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The TS Dating Advisor - Free TS Date Advice.
Dating Advice for the Transsexual Relationship.


The TS Dating Advisor provides some free TS date advice. Email addresses will be withheld. We'll do our best to answer all serious questions on the subject of TS dating. This is the best place to get dating advice for the budding transsexual relationship. We will not respond to requests to be hooked up. That's not our job.

From: Deleted
To: Deleted
Sent: 9/5/2013 12:05:50 A.M. Pacific Daylight Time
Subj: I read your article on transwomen and I have a question.

I read your article, "Having Sex With a Transsexual Woman: How to Make Love With the Transsexual Female," and I have some questions. Here is some background information. I am getting close with a transwoman and debating whether to date her seriously. I want to emotional prepare myself if I decide to have sex with her.

I was wondering, what is the range of penis size a transwoman can have? Is the range the same as normal males, or smaller? Can a transwoman ejaculate? I don't dare ask these questions of the transwoman whom I am getting close with, at least not yet. I can accept who she is, she is a lovely person. If you could answer me, that would be great, thanks!


If she's been going through hormone replacement therapy, there's a good chance the penis is smaller than usual. Female hormones also affect a TS's ability to get hard. Ejaculate? Usually, yes. Good luck.

From: Deleted
To: Deleted
Sent: 8/23/2013 5:35:02 A.M. Pacific Daylight Time
Subj: Post-op.


I've been dating my girlfriend (pre-op) for about six months now and in December she will be getting SRS done. I have a few questions but not sure where to look. First off I'm hung a few inches above average. Will I hurt her if we try to have vaginal sex? No STD's, we are both clean. If I were to cum inside her vagina, it won't cause any problems, right?


Vaginal depth is usually around six inches or less. If you hit bottom and keep driving in, yes, you can create discomfort. Cumming in her vagina won't create problems. Good luck.

From: Deleted
To: Deleted
Sent: 8/20/2013 12:46:01 A.M. Pacific Daylight Time
Subj: Help!!!

I recently went on a date with a girl and I was wondering if someone on here could help me figure out what I did wrong.

Background info: We both graduated pretty recently. We are 18. We met in our freshman year of high school and became pretty good friends. Around the junior year, when she was 16, our friendship really developed because she had started hormone therapy. I always had a crush on her, but I kept it on the down low because I didn't think my feelings were reciprocated.

We have always been there for each other. In our junior year, she was having a lot of problems. For example, she had tried out for the cheerleading team but they told her she couldn't wear a girl's uniform. Well this made her really upset. So to fix it I talked to my football coach and told him that if she didn't get to be a cheerleader like she wanted, I was done playing back up QB and WR, and that come basketball season he might as well forget about me playing. Well, long story short, she got to cheer in the uniform she wanted.

Then in our senior year, I was having trouble getting scholarship offers. As you can probably tell by my writing, I'm not very smart. Then she tutored me for the ACT and helped me in my classes and I finally got the GPA and ACT score I needed. In graduation, I was told I got a full ride to a college (whose name I won't mention.) So feeling on top of the world, I told her how I felt. And she said she liked me too. Now here is where the date starts.

I showed up in a tux and the whole get up because we had agreed to go somewhere nice. I brought flowers (not sure if this was bad) and gave them to her. She looked so beautiful. I opened the car door for her and everything. When we got to the restaurant, I opened all the doors for her and kept to all my manners that I had been taught.

When we got the check, I started to pull out my wallet and she said, "Let's go Dutch." This kinda shocked me and I explained to her that I was taking her out and she had dressed up and everything for me so the least I could do was pay. I mean, we had hung out before when we were just buddies and I had always paid, so why would it change now? So she let me pay. (Is this where I messed up?).

We left and I took her home. At her house, I parked and walked her to her door and she asked me if I'd mind coming in and staying a while 'til her parents got home so she wouldn't be alone. Of course I didn't mind. I mean, I've always liked protecting her and being with her. I said yes and we sat on her couch then cuddled while we watched a movie.

Well, her parents got home and when I was going to leave she asked me if she could repay me for dinner and for staying with her while her parents were gone. And I said, "Yeah, how about a kiss good night and dinner again tomorrow?" She laughed and explained she meant a little more than a kiss. (Here is where I think I messed up.) I told her that I don't think we should and she just kissed me and I left. Now she won't text me back or anything.

Did I offend her by saying no about having sex? Because that's the last thing I wanted to do. I don't want her to think I'm not attracted to her because I really am. I don't know. I was always told to wait 'til marriage or at least past the first date. Don't get me wrong, I really wanted to but I don't think it's right. It's not like with other girls, I guess I just respect her more or something.

It's just she looked so beautiful and innocent and pure and I don't deserve her. I don't know how to explain it. So what should I do or say to her? I don't want to lose her over something like this because I do want her. So much. I just thought it was disrespectful to have sex on the first date. Please help me.

--Tom J.

Hello Tom,

She's obviously very comfortable with you and enjoys being with you, which is a good thing. However, it's not uncommon for young folks to misunderstand or overreact, simply out of inexperience. She may have done exactly that. My guess is she thinks you rejected her because of her boyish body, male genitals, or whatever.

You clearly know where she lives. Go knock on her door and ask for the opportunity to explain. Or mail her a nice greeting card (actual card, envelope, stamp) and enclose a letter explaining yourself and your feelings. You can do that well; you did so with me. Apologize for any misunderstanding. And tell her you want to see her again.

With any luck you two will resume communicating. Good luck!!

From: Deleted
To: Deleted
Sent: 2/1/2013 2:10:06 P.M. Pacific Standard Time
Subj: I need help.


I have a problem. I think my girlfriend is running an escort service. She is a very passable TS girl. I found notes saying thanks for a good time. When I ask her what's going on, she said it's an old friend. And she had more money than before? And my neighbor said there have been people stopping by at all hours, day and night. I have a crazy work schedule and travel to other places. I asked her again and she said it's nothing and it stopped for some time, but lately it's started again. She also has a strong sex drive; she was to do it all the time. I need help, what should I do?

--Travis T.

I dunno. Most adults have a job of some kind. If her's bothers you then you should find someone else. But if you don't mind, just ignore it and be part of her life. Apparently all the sexual stimulation she gets pays off for you, since she wants sex all the time, which is not a bad thing at all. Here's the basic question: Do you mind sharing her?

Subject: Bringing my TS girl to my home.
Date: 1/16/2013 9:44:07 P.M. Pacific Standard Time
From: Deleted
To: Deleted


I have been dating a beautiful TS woman and we love one another but I have some doubts about how passable she is. To me, she means the world. I already explained her to my close sister and she approved. I guess I'm just afraid of what someone might say who sees her and me together. What if a family member notices us or even my next door neighbors? Please help I don't want to make her feel like I'm ashamed but I'm assuming it's a natural feeling I'm having. I don't know how to explain it with out hurting her feelings.

--Mr. D.

If you love her, you accept her and you defend her. Dating a TS can test your willingness to say unpleasant things to people you know, such as:

"It's none of your business."

"Well, she's a woman now, so deal with it."

"I don't care what you think."

But if your love is conditional on how well she passes, then you don't really love her.

Good luck.

Subject: Question.
Date: 11/12/2012 9:56:03 A.M. Pacific Standard Time
From: Deleted
To: Deleted

Hi, I have done much research to know that I am not alone in my situation. But I am still very confused and would like some guidance/education to help me process this! Okay, here goes.

In the beginning of the summer, I saw on my boyfriend's iPhone emails to and from Craigslist. He made ads himself, responded to ads, looked in local and non-local areas. He went as far as to put real pics and real info about himself and even one time mentioned having a girlfriend. He promised to not do this again.

I should note that I am a psychotherapist with a specialty in addiction. I know that if someone enjoys something they will not just stop but usually get better at hiding their pleasure when it may be frowned upon. So I did my best to trust and practice having faith.

Just the other day he handed me his phone to watch a video and I guess on the new updates with the iPhone all you have to do is hold your finger down on the browser 's back button to pull up all the history. Well, to my surprise, there were tons of sites for Craigslist, m4m and t4m. I wasn't as shocked as last time, it just confirmed my belief from before that he wasn't going to stop.

I waited for a couple of hours to pass then I gently brought it to his attention and expressed how betrayed I felt. After all, he had said, "I will never go back on because I know how much it hurt you!" All I got from that conversation was: "I am not going to talk about this now. Anything I have to say will just come out the wrong way. I;ll get back to you."

I was shocked but figured I really wanted an explanation so I have held back. It has been about two weeks and his birthday is this Thursday. I didn't want to bring it up this week and ruin it and I figured he might be thinking the same thing. So I am trying to hold out until end of November because next weekend is Thanksgiving! Ughh, I don't know what to do.

It bothers me for a few reasons: He made it very personal in the ads and responses but says he has never met up or had sexual interactions with these people, no phone number exchanges just does it because he thinks it is funny. He says he's been doing this since age 16. His mom caught him once an asked if he were gay; he said no, and I am the next person that caught him.

He gets very defensive when asks about "likening t4m to being bi or gay. He says, "I know who I am and I am comfortable with my sexuality and do not like guys; I just do it when I am bored and I think it's funny." I don't know how much to believe of this. I accept him for who he is, and heck, who knows? Maybe I might like something "non-routine" as well!

I am always trying to bring up new sex ideas, toys, positions, anal. But he is more on the shy side. He says, "I don't know, I have never put that much thought into it." I laugh to myself because for someone who is doing what he is doing, I for sure would only expect him to have some kind of fantasy ideas or interests. But nope, he always lightly switches the convo.

But we have a great sex life, at least twice a day if not three or four times. We do experiment, but he shies away form toys; has never had anal with me even though I offered. Any advice would be greatly appreciated!! Thank you for your time!

I regret not having answered your query promptly. Sometimes I get incredibly overwhelmed here. If you still want my opinion, here goes: I don't buy his "it's funny" story at all. I believe he is concealing a side of himself. He's divided his life into tight little compartments. He's "shy" about sexual variety because that would take him over the threshold into another part of his life that you aren't supposed to know about. My opinion is that you are being lied to. If I were in your shoes, I'd walk. Away. Good luck.

Subject: How are you?
Date: 9/14/2011 2:20:35 P.M. Pacific Standard Time
From: Deleted
To: Deleted


I just want to ask u about my relationship. I have been going out with my T-girl now for about eight months. I love her but we having a problem in our sex life. She's almost 98% top and I love to make her happy, but sometimes I don't wanna be a bottom. She tried to be the bottom once but she didn't like it at all. Also, she's the kind person that likes to have sex all the time and she likes me because I please her all the time, but I wanna try to top sometimes. What can I do? And why do you think she likes to be top all the time?


Why does she like to top all the time? Well, who can really say about reasons when it comes to sex? You can continue as you are with her. Or, if it hurts too much, use a better lubricant. Or you can both go together to a sex therapist or counselor and discuss the matter, or I suppose you can find someone else. Really, that's about all I can advise....

Subject: Some much-needed advice?
Date: 9/26/2011 11:44:45 P.M. Pacific Standard Time
From: Deleted
To: Deleted


My name is Jonathan, I'm in my 30s, and I came across your website while looking for advice on dating/friendships with TS women. I have come across some very beautiful and kind women and that's even before I came upon your website.

My question pertains to the women who have gone out with me and those who didn't but that I still chat with, and why they seem to be all over the map on what is appropriate and what isn't, what you can and cannot say. I have come across some very kind and understanding women who give bits of advice but even they seem to do the same thing. It is really starting to get frustrating because when I meet the right woman for me (and I am very confident I will), I do not want to mess anything up. I am sorry for coming across as very frustrated but I thought maybe you could give me some help or advice. Thank you very much for your time.


People will differ. I just treat a TS precisely the same way I would a genetic girl. Some won't even be a close match, some will be flaky, some will be morons, some will be control freaks...it's just part of life. If you don't like some girl you've gone out with, move on. Dating is a bitch. For me personally, I keep sex out of the discussion for the first few dates. One T-girl I had been out with three went totally silent on me when I invited her over to watch a movie and to possibly play around. She won't even talk to me now. Some people need to get their heads examined, either that or she was just using me to go to restaurants, etc. Either way, to hell with her. Next? LOL
Good luck, man.

Subject: Tsgirl Question
Date: 12/4/2010 3:31:13 A.M. Pacific Daylight Time
From: Deleted
To: Deleted

Hi, my name is Dennis and I just happen to come across your site and I have a few questions to ask pertaining to sex with a post-op TS girl.

I've been dating my girlfriend, who is about a year and a half post-op, for almost a month now. I would like to have sex with her and we've been talking about it, but I really dont know what to expect. She tells me all the time that her pussy is just like any other woman's pussy and I want to believe her -- really I do -- but she showed it to me and it just kind of looks like a dick reincarnated.

She has been honest with me from the start about her being trans and I truly appreciate and accept that. She is very beautiful and when she first told me I didn't believe her, and when she told me she was post-op, I guess that made it even easier for me to accept that she used to be a boy.

I'm not a virgin and I know what pussy looks like. I always thought it looked kind of cute and sexy and I enjoyed playing with my partners, but I don't know if I can truly say that now. I know I probably sound like and idiot but my question to you is, did you feel the same way when you first started dating TS girls or not? And does sex with them really feel the same with them as it does with natal girls?

I really need to know 'cause what I love most about having sex with women is that warm, lumpy, silky feel inside of a woman's vagina. I just need to know if TS girls feel exactly the same and whether I would be able to tell the diffrence. I really care for my girlfriend and want to intimate with her but I just need to know from someone whos been there. Thanks.


The appearance and functionality of the vagina is a function of the surgeon. Some are completely convincing, others look like burn holes into the body.

An artificial vagina has no way to lube itself, so you will need to use something slick. Any sexual lubricant should work fine.

The average depth of such a vagina is around 5" to 6". A guy with, say, 9 inches of dick is going to bottom out. In my experience, a "new" vagina can be uncomfortably tight. It can take a while to (forgive the expression) break it in.

Good luck to you.

Subject: I'm confused
Date: 12/16/2008 12:08:17 A.M. Pacific Standard Time
From: Deleted
To: Deleted

Maybe you could help me. I am a man who is sort of in a relationship with a transgendered woman who lives here in my neighborhood. We hang out at the local watering holes, talk on the phone, etc., but I am reluctant. I understand how she wants to be treated just like any other woman and I respect that, but it just kind of seems that it's gotta be her way or no way.

She doesn't seem to care that this would be a big step for me. It's all about her struggle and not mine. I truly do care for her but she has issues with a previous relationship that have nothing to do with me. I'm afraid that If I invest a lot of time, I could end up empty handed and feeling like a complete idiot for pursuing this. I know there's no sure things in any part of life, but I don't understand why she can't cut me some slack.

I would love to be with her fully and openly but I fear that if she flakes out on me then no other woman in my town will date me (People are stupid here.) My so-called friends already make fun at me for being friends with her. I hate this but I think I love her and this has been going on for a year and a half now.

I'm sure you think I'm an ass and I apologize, but I'm very frustrated. Neither of us are seeing other people and it seems like I have two choices, take a chance with her on her terms and face the bullshit from my friends and family if it doesn't work, out or just let it go. What do you think? I would be grateful for any advice.



Do you treat her as you would any other woman, or as something else? It sounds as if she has laid down certain exceptional conditions of treatment and she expects you to accept them. If this is the case and her conditions exceed what most women would expect of a man, and if you are balking at meeting them (as you appear to be), then I recommend that you walk away.

Good luck to you.

Subject: Some Questions about your article...
Date: 1/29/2008 9:02:19 P.M. Pacific Standard Time
From: Deleted
To: Deleted


I just wanted to start off by saying I read your article and it answered a bunch of my questions, and it has made me want to open up to the possiblity of a TS. I have recently been talking to one online, and between you and me, I like her. She is pretty and good to talk to, but I can't tell if she is being serious about all this or not, also I have many friends and I love going out and partying and whatnot, but like I am worried that they will see her for something else and make fun of meo. Some of my questions are, is it wrong for me to want her to be well hidden? How do I bring up this subject with her? and do you have any suggestions on how to go about this?

It is a possibility they will make fun of you, but we are assuming they even know that she's a TS. If she's very passable they probably won't know, and why tell them? Is it any of their business?

Subject: Dating advice
Date: 10/22/2007 8:21:38 AM Pacific Daylight Time
From: Deleted
To: Deleted

Hi Michael,

I am a 25-year-old post-op and met this guy on a dating site here in South Africa for transsexuals. We started talking and he was very eager, but I felt that I had to tell him that recently I just broke up with my ex and that he is coming over to get his iPod that he left at my place while we were together. This guy freaked out and told me that I have issues and that I should have sorted those issues out because he has been hurt before by women. He said he is only looking for one partner to have a long-term relationship with. It has been a very challenging relationship for me, since I had to call him and explain that my ex is only an ex, and that I love him and would want to move in with him.

Nevertheless, to cut a long story short, I think I have triggered in some way his fears and anxieties that he had and that he had suffered all along. He also tends to have a low self-esteem and told me that he had a dysfunctional family when he grew up. I was prepared to help and stand by him through all this, but he keeps withdrawing and this really tends to hurt me. I have spoken to him before and he promised that it would never happen again, but he still builds a wall around himself which is virtually impossible to penetrate.

He is very unsure and very insecure and needs reassurance. He told me that he wants commitment but wants to take it one day at a time. I try to go at his pace since he is fragile, and try to be gentle at the same time, but he doesn't call me, and when I asked him he said that he doesn't want to think and deal with it now. I got upset because I think he owes me an explanation as to whether he is still with me or not. He replied that he couldn't answer my question because he still has questions but will deal with it after his exams.

We got into another argument and I lashed out at him asking if he wants to be with me because he put on the site that he is looking for his "she-male queen." I need to also be aware of this so that I know where I stand, because I am not "chick with a dick." Lots of things go through my mind and sometimes I can't help but guess because he is not forthcoming with me. When I confronted him with this, he dropped the phone in my ear and wouldn't take my calls. I know it was stupid of me, but I am also human and he wouldn't even give me the opportunity to show him and prove to him that I wouldn't hurt him, and that I will love him in a very special way.

We are of different races and I am extremely pretty and passable, so he always questions me when I do speak to him, as to why would a beautiful Asian lady like myself would want an ordinary, simple black guy like him. I am in a lot of pain right now and I would appreciate your insight into this matter. I don't know why this has to happen to me.

Kind regards.


He wants a chick with a dick, and that ain't you. That's Problem #1. Secondly, this guy needs to get into therapy and resolve some personal issues. You say that he asks of you almost every time you call, "Why would a beautiful Asian lady like you want with an ordinary, simple black guy like me?" That is the wrong question and unfair to ordinary, simple black guys. Instead, he should be asking, "Why would a beautiful Asian lady like you want with an insanely jealous, insecure and demanding bisexual guy like me?" You can do better, and I suggest you say goodbye to this fellow and move on. Or, bide your time until his psychotherapist (and/or psychiatrist) pronounces him "cured." Good luck to you.

Subject: Asking for some advice
Date: 7/17/2007 8:11:17 AM Pacific Daylight Time
From: Deleted
To: Deleted


I have been coming to TSGirlfriend for some time and following the advice page. I have seen wonderful advice to wonderful people. So here is my situation:

I have been communicating with a gentleman for some time now. We have exchanged phone numbers. Our conversations start off wonderfully, we chat about what he did during the day, and I share what has happened in my life. It is a real connecting moment, and I truly enjoy feeling like I am a part of his life and sharing mine with him, limited as it is. We have shared our long-term fantasies, the desire to live long happy lives with someone special. Images of domestic life with each other. I have shared things about myself that I never thought I would with a man. I have a lot of emotions on the line here.

But the problem arises inevitably in every phone call. It turns to his sexual desires. Though it is kinda nice to know I am desirable to him sexually, it is very unsettling. I have told him many times that it does make me very uncomfortable, he acknowledges that and the conversation changes for a time, but will return to that topic.

He reassures me that he does not see me as pre-op, and that he only sees me as the woman I project. He stated that his desires do not involve that part of my anatomy, thank god! But I have stopped calling him, and as of today he has not contacted me.

Here is my question, does he see me truly as a woman or just the object to satisfy his desires? Or do I try to change myself to make it easier for me to accommodate this aspect of his personality?

I have asked several people in the chat room but did not get a response from a man's piont of view. I would love to hear your feelings on this. Maybe someone else can learn from this situation, also.



Hi Tammy,

Given the fact that you two have not yet met, I can only offer advice based on what you do know for a fact. Yes, obviously, he's interested in sex. He apparently denies thinking of you only for sex, but the evidence contradicts that. You didn't mention how much time has passed since you ceased calling him, but if he's not trying to reach you, it indicates there is little to no emotional attachment on his part. I don't think he's telling you the entire truth about his interest in you. It would not be a good idea to change to accommodate his desires. The end result of that will be to make you very unhappy. Good luck to you.

Subject: nervous and frustrated
Date: 6/24/2007 8:56:15 PM Pacific Daylight Time
From: Deleted
To: Deleted


I seem to be having a bit of a dating problem. I am a 23-year-old pre-op TS and I recently met a 22-year-old on a motorcycle forum. He and I obviously share a lot of the same interests, and we have gone riding together, and out on a few dates. He seems to be really into me, and I am really into him. But he has no idea of my gender, and I have no idea when to tell him or how. I don't want to freak him out like super bad.. I don't know what to do. I need help badly.


Hi there,

You do need to tell him and now is the time. You have to open up and put your feelings out there, you have to tell the truth, and you might get trashed when you deliver the news. It might be beneficial to print out some info on transsexualism and have it with you when you tell him so that he doesn't think you're just a guy in a dress who is playing a game. Some of the info at TSGirlfriend.com might also be worth showing him, such as the article on how to date the pre-op TS.

You need to consider tactics here. Some guys will react very badly, they might shout, a few might even get violent. It could be to your benefit to reveal the truth in a public or semi-public place. Having others around who could witness any bad behavior might mitigate any such response.

If I were the guy you would tell this to, I personally would prefer, first of all, that you lay your feelings on the line, say that you care for me, and ask me how I feel about you. Then, I would want you to say that there is something I need to know before this goes any further, and add that you hope it won't destroy our friendship.

I think probably I would react most favorably if you explained that you are a woman, have always been a woman but were born into the wrong body, and that you will correct the body so that your outside matches your inside, as soon as you can. And then I would want you to say you really care about me, and that if I care about you then I should read a couple of things before deciding what to do.

And then I would want you to show me something that clearly and quickly explains what a transsexual is, and that info should clearly differentiate TS from TV/CD.

It is possible that he already suspects something along these lines. If it is a total surprise, he may well be hurt and confused, which is why you need to put your feelings out there and why you ask how he feels about you. Let him see in your eyes that you are feeling very vulnerable with this revelation, and that will tell him that you are not playing some silly game. The info about transsexualism will help clear up the confusion.

Good luck to you.

Subject: Confused
Date: 6/10/2007 7:03:03 AM Pacific Daylight Time
From: Deleted
To: Deleted


I have a friend and she is a pre-op transsexual. I have meet her through another friend who has since pased away. After years of going out and helping her with personal items, getting an apartment and cosigning on it, helping with the rent, I started have more feelings for her. We would go to gay clubs, where she is comfortable. I dropped her off at the apartment and we started to kiss and make out. After doing this for a couple of weeks, she started to give me a hand job.

After going shopping with her for her birthday, she gave me a BJ. While we are doing this, I was afraid I might hurt her feelings and did not know where I should go with it. I started to like it more and more, and began looking for it. We stopped it for a while, and then we started making love again. This time, I started giving her a hand job, trying to get her off. After a while, I noticed she was hurting, so I stopped and I left. We have spoken to one another until we went out next weekend. We chatted about what happened and she was shocked that we crossed the line that friends should not have cross, unless we were willing to take it to the next step.

I wanted to take it to the next step, but not hurt our friendship. She has been giving me mixed signals, she stated you need to know this if we get married. I love her and don’t want to hurt her; her heart has been broken before. I feel that I’m using her as a fallback. I want to find a woman to marry and have kids. If I don’t find this woman I would married my TS friend, but I’m also afraid of my family not accepting her. Am I hurting her? Playing with her feelings and mind?


I think you need to meditate on your own feelings. Nobody wants to be the fallback person. It isn't fair to her to be sort of strung along, maybe for years, and maybe suddenly dropped in favor of another. If you find her intriguing and wish to pursue a relationship, then your focus needs to be only on her. Insofar as your family is concerned, is the choice of your relationship any business of theirs? Good luck to you.

Subject: website page idea
Date: 3/23/2007 9:56:32 PM Pacific Daylight Time
From: Deleted
To: Deleted

First off, you have a good website and promote good ideals.

I'm looking for a page that gives advice to guys that the girls in the chatroom probably wouldn't want to date (that includes me). From what I've read, I'm sadly the typical type of guy that T-girls have to deal with. In part, there is an element of sexual novelty, and the porn industry hasn't helped that in any way. Lots of Internet porn hasn't done me any good, and I know I'm more likely to objectify a girl because of it, but I do try hard to recognize that all those pictures are of real people, and sometimes, I can even see some sorrow in their eyes.

I'm 22, never dated or had a girlfriend, might be bi, but questioning that happened more recently. I started looking at transsexual porn when I was around 14 or 15. I wondered if it made me somehow not-straight, but I'm not as worried about that. I have a feeling I want to be somewhat submissive in bed, but I'm still a virgin, so that's just a guess.

Basically, I'm wondering if you have any advice for someone like me. I know what the girls in the chatroom are looking for, and it probably isn't me; I can respect and understand that.

Thanks for reading, and any observations would be appreciated. I'm trying to figure this out, but most people in my position aren't very open about it, and the two things people think of when they hear the word "transsexual" are Jerry Springer and San Francisco (which luckly, in a way, I live near).

Thanks again.

You, my good man, need experience. Get out there and socialize, take up some activity where you have the opportunity to interact with others (women, men, whatever). Make friends. Move, move, move!

Subject: Hi - From South Africa
Date: 1/5/2006 1:36:44 PM Pacific Standard Time
From: Deleted
To: Deleted

Dear Ms Editor,

I found your page extremely interesting -- most probably as a result of the fact that, as a result of demographics (and maybe a bit of it being unknown), there are not many TS girls in South Africa. I know that there used to be a very active community of transgendered people seeking reassignment surgery here -- but it appears they all have emigrated. That is even with South Africa having changed its legislation that allows people who changed their sex to easily change identity and enter into legal marriage.

I view myself as a heterosexual male, i.e., interested in females, but seems to have less luck with them: Two failed marriages!

Out of curiosity, I went on a date with a pre-op TS girl, and even had sex with her.

The interesting thing to me is that I was neither revolted by her penis nor extremely attracted to it, either. What I did find is that I seemd to "connect" better with her on an emotional and spiritual plane than with any natural-born female I've ever been with. (And the sex was better too!)

Unfortunately, I let go of her. I didn't know how to handle the whole thing. I corresponded with a few TG girls here in SA and found that there was "something deeper" in their conversations -- something difficult to articulate but still something I've never found exchanging views and correspondence with "real" women. It's like the grass is greener, the sky is bluer and life infinitely sweeter for some of these TS girls. That appeals to me, being a romantic at heart.

Since then I've looked up a few sites on the Internet, and apart from the ones clearly intended for pornographic purposes, I really enjoyed to read about some of the experiences the girls had in their quest to change to female.

The whole issue is now confusing to me -- would it not be the best thing if one is attracted to a particular lady and then find out -- sort of by the way, not that it really matters, that she is/was a genetic male? It sort of fits my concept of a romantic story. Why would one then purposefully search for a TS girl and then choose the one who fits with one's one profile?

The reason I ask this sort of philosphical question is the following: Though nothing came of my relationship with the TS girl I mentioned, it has created so many questions and has confused me. There was a magic with this TS girl I've never found with a "real" woman before. It had me so confused I went for psychological counselling fearing I was gay/bisexual without even knowing it. It did not appear from the counselling that either was the case.

It will be interesting to find out whether there are any theories behind this one. Obviously South African psychologists are not familar with attraction to transgender people. In a popular magazine over here, there was an article on shemales in Brazilia (apparently they call them bombardiera), but the article claimed that these ladies exist because men can then have a relationship with another male without feeling guilty about latent homosexuality.

This is definitely not the case with me. I appreciate a fine woman just as much as the next guy, but believe it is not what you were born with that makes the person, but how that person defines him/herself.

So I would really appreciate it if you give me a view on the following:

Am I just starry-eyed about one romance and have unrealistic expectations as a result of that?

Was I correct in my feeling that this TS girl, and maybe all TS girls, could perhaps be more accommodating, romantic and understanding in a relationship?

Do you think American TS girls would at all be interested in corresponding with South African residents with a view of meeting and exploring the possibility of a more meaningful relationship?

Thanks for the interesting site.


I've been married in the past. I have also had a long-standing interest in transsexual women, I think because they are more interested in being feminine than are genetic women in the USA. Some years ago, when back in the dating pool, I also intentionally sought out TS women and entered into a relationship with one. It's been over four years now and still going strong. It is perfectly OK to acknowledge that a TS is a romantic possibility and proactively seek that person out.

If you are attracted to a TS girl because of her femininity and not because she's a chick with a dick (if pre-op), then the basis for your attraction is heterosexual. Treat any TS woman as you would any genetic woman. The romantic possibilities for either should be about the same. Trust me, the TS woman wants to be treated like any other woman. As a side note, TS girls are often suspicious about the nature of men's interest. Many men who approach them are bisexual. The TS girls I know are as little interested in bi guys as are genetic women.

TS women know what it's like to be a guy. That is a serious advantage over the genetic girl, in my opinion. On average, I would say a TS girl would understand you better.

Some American TS girls would be willing to correspond with SA men, if they had some reason to believe they are serious about a future meeting and not just leading them on. Good luck to you.

Subject: my friend is a ts, a question for you
Date: 8/2/2005 7:19:54 PM Pacific Standard Time
From: Deleted
To: Deleted


I have a good friend who is a TS. She had her surgery about a year or so ago. Recently, she met a man and he moved in with her within a month. They've been together about three months now, have talked about marriage, but my friend still hasn't told him about herself.

I've been to her house for dinner to meet him, and found I was very uncomfortable because I had been told to be careful not to say anything that might clue him in. I felt like I could never get to really know him, and that I was part of a cover up of sorts.

She has grown children and has photos of them at her house, and has told him she is their mother. I had to tell her I didn't want to be around them as a couple under the circumstances, and she now doesn't want to be my friend and feels it's a betrayal on my part. She says she'll never tell him because he might leave her if he finds out. I worry about her safety if he finds out another way. She told me two psychiatrists told her NOT to tell unless they were going to get married!

I've been doing research and found your website and others that encourage TS's to disclose this information in relationships. So, are my concerns valid, am I a shitty friend, or what? She said she HAS to lie forever to him because "her dream is at her fingertips." Is it OK for him not to have a choice? Just curious what the prevailing consensus is on this. I really enjoyed her company before I had to be part of the deception.

Thanks in advance for your response.

I don't blame you for wanting to keep your distance. You are correct, you would be part of a cover up. I doubt very much any psychiatrist told her to keep it secret. I think you ought to tell her that you cannot support her actions because she is being dishonest, and that you don't wish to be part of her conspiracy. Also tell her it is your view that she needs to disclose her past as soon as possible.

She is in serious denial if she thinks she call pull this off. This whole matter will blow up in her face at some point and you really don't want to be around when that happens. It could get violent. Say your piece, offer your advice to disclose and walk away. You aren't being a bad friend. You're being a very sensible, good friend. Good luck.

Subject: HI From Leslie
Date: 2/19/2005 1:03:25 P.M. Pacific Standard Time
From: Deleted
To: Deleted


I'm a post-op TS, and still quite young. I'm currently in a relationship with a married man. I know, a no-no. But he promised my a while back that his marriage was over and he was getting a divorce. Now he has told me that he has changed his mind and wants to stay with his wife. Then on another day, he told me that he wants to stay with his wife and have me as his girlfriend on the side. I'm not at all looking for that kind of arrangement. I'm looking for a full-time one-on-one comittment. His wife found out about us having an affair and she's furious. Also, I told him of my post-op status, and he totally refuses to believe me. What do I do?


Walk away girl. This guy is a liar and a cheat.

Subject: Unsure and now in doubt
Date: 12/28/2004 12:46:07 A.M. Pacific Standard Time
From: Deleted
To: Deleted

I have been living with a beautiful pre-op TG female for about 10 months now. I have been very happy and was enjoying our life together. I came home from work one evening and caught her with another man in our apartment. I was so heartbroken that she would do that to me. She said it was her first time, and I believe her, but she does a lot of things that really hurt me and she doesn't understand why it bothers me.

She constantly talks to people online and over the phone, she has various profiles on different sites. She lists that she is single and not looking, even though we have been together for so long. I have tried to ask her to at least say that she is in a long-term relationship, but she says that since people supposedly doesn't pay attention to profiles that it is unnecessary to say she is in a relationship.

I have been dealing with this as best as I can, but it is hard for me. Every part of my being is telling me to leave her and be done with it, but I truly care for her and want to work through this with her. I fear that if I leave now I may start a cycle that will be bad for her. I try to remember that she is young (20 years old), and still learning. I am 29 years old and I remember how I acted when I was 20. I fear that with her being TG that she is being approached just for that reason and I fear that a lot of the people that she speaks to have dishonorable intentions and won't respect her as a person. I would like to hear from someone with experience in transgendered women.

With a heavy heart,


This is a people problem, not a transgender problem. I doubt what you caught her at was the first time, and I wonder whether she is hooking behind your back. At the very least, it's evident that she is being promiscuous. She has no reason to have profiles or personal ads up, or to be soliciting attention from other men. My recommendation is to insist that she stop. If she leaves you as a result, consider yourself to be fortunate. I think you're being lied to and taken advantage of. Good luck.

Subject: A Comment & Question
Date: 6/3/2004 10:58:37 AM Pacific Standard Time
From: Deleted
To: Deleted

I just read the article, "T-Girls as Women -- Your T-Girl Should be a Happy Girl." These are things I do normally. However, it's good to go back and review how not to screw-up.

I've noticed one thing. When I do these things and make a woman happy or content, her girlfriends will do their best/worst to interfere. The old saying, "Misery loves company" is very true. They're not happy, so why should anyone else be? That is the only thing I can think of that I do not know how to combat. How do you keep interfering women out of a relationship?


I suggest you tell your lady that you and she need to have a talk and you lay it out for her. Cite examples of their interference and let her know how much it bothers you. Then tell her that you and she need to come up with a solution. She may not regard their meddling as interference, and she may also not be aware how unhappy it is making you. Good luck.

Subject: Possibility of date being an escort...
Date: 6/2/2004 3:55:14 PM Pacific Standard Time
From: Deleted
To: Deleted

A few weeks ago, I received a message on an adult personals site from a local TS woman. I messaged her back and we started communicating via email and we exchanged photos. Shes new to the city and mentioned that she really wanted to go to the zoo in our town, so I offered to take her and she accepted eagerly, she even said
that it would be the coolest date. Well there are a few things that have made me suspect her of being an escort: First, shes VERY attractive and passable; shes making it really easy for me to ask her out, almost too easy; and in her old profile she has her profession listed as "Entertainment." But she hasn't SAID anything that would make me suspect this. In fact, she told me she was looking for a man who desires her mind as well as her body, and that doesn't sound escort-like to me. So I'm a little paranoid about this. Is there anything I should be on the lookout for?


Requests for cash, donations of jewelry or whatever. Escorts charge for dates, one way or another, and up front. They don't send you a bill in the mail. As far as "entertainment" as her profession is concerned, maybe she plays accordion in a rock band. ;-)

Follow up: She proved to not be an escort. They had a great time on the date.

Subject: need help
Date: 4/21/2004 9:55:34 AM Pacific Standard Time
From: Deleted
To: Deleted

I have had a problem with a TS lady I was corresponding via the Internet. I seemed to be making her angry and did not know why. I read the inmformation on your site and then saw why she was getting annoyed. I had been doing what it says on your site not to do - sending promises of eternal love without having met her, etc.

I can see, as your site says, you wouldn't do that in a coffee shop or a party to soneone you don't know, there is no reason to do it over the Internet. I could not before see her reasion and she did not give me the reason she just was annoyed. I would know not to do the same in the future and to be a bit cooler but there is a problem.

Recently we had a very bad row -- it ended with her calling me a "faggot" (untrue), and becaue I felt hurt and upset, I called her I'm ashamed to have to say, although she is the most feminine and more of a woman than any GG I've seen, "a man with fake boobs." (also untrue).

Although I still like her very much and would be cooler in the future, would you say there is any chance things are not too broke to fix and may in the future be repaired?

Thanks for any advice you can give.

--Bryan H.

Hello Bryan,

Ouch is the word. Do you have her address? Try sending her a dozen red roses with a note attached, suggest you say you lost your cool (and you are very sorry about that) and would like to talk. If you don't have her address, try sending a greeting card from online, bluemountain.com has a great selection, and again apologize for losing your cool. Tell her you would like to talk and work it out. That's about as good as it gets. Good luck.

Subject: Dating advice please!
Date: 3/14/2004 8:29:45 PM Pacific Standard Time
From: Deleted
To: Deleted


I need some dating advice. I got an email a few days ago from a TS girlwho saw one of my letters on your site so I emailed her and two days later we had a long conversation on the phone. Problem is, she seems to be downright eager to get into a committed relationship even though we only had the one conversation. Now, I'm feeling guilty as heck but I think one conversation isn't enough to make a commitment. I'll forward copies of the emails for you to read.

Am I misreading the situation and overreacting? Please give me your opinion.



Hello R.K.,

She does seem eager. Clearly, you do need to proceed at a pace you feel comfortable with. The best way to find out whether you are misreading the situation is to continue talking and see whether she actually is pressing for a quick commitment. There's no harm in continuing the dialogue. Then you need to ignore any pressure and decide whether this is too much too quickly, and act accordingly. Good luck.

Subject: What am I doing wrong?....
Date: 2/13/2004 9:49:24 AM Pacific Standard Time
From: Deleted
To: Deleted

Thanks for the information on dating a TS woman. But trying to get to that first date is one of the hardest things I've ever done.There is one woman I'm interested in. However, being honest (no game playing) and being a gentleman has gotten me nowhere. She will not even give me the time of day. I have not said anything that could be misconstrued as just wanting a curiosity date. Yet, I have placed with all the others. I was even told, "I know what you really want!" and, "What is your angle?"

I'm really getting to the point of throwing my hands up and walking away. What am I doing wrong?


So walk away. It seems clear to me she doesn't want to be involved with you, or perhaps any man. If she really believes what she told you, that's unfortunate, for her. Believe me, there are lots of great TS women out there who would love to hear from a gentleman.

Subject: TS Dating Advice
Date: 1/12/2004 5:16:43 PM Pacific Standard Time
From: Deleted
To: Deleted

Dear TS Dating Advisor,

I am currently dating a beautiful pre-op TS woman and I have some questions and concerns that I would like to share with you in hopes that you may shed some valuable insight.

We have been dating for about a month now and there are some hurdles that are coming up that will soon have to be acknowledged. First let me preface by saying that my GF is very, very passable and hotter than most genetic females that I have known or dated. I find her to be intelligent, humorous, and a great communicator, qualities that I seek in women I date.

The first issue is that of the friends/family acceptance issue. I am tight with my friends and family both and don't think that they will accept me dating a TS. She is feminine, soft and tender to me she has the perfect woman's body and she is in no way masculine. She lives in the same town as I do and we go to a lot of the same places (clubs) so it is just a matter of time before we run into my friends. We have discussed this several times and she is amazingly understanding so far. I suggested that we stage a "first" meeting out some night so that we can at least get it to a level in front of my friends where as I at least meet her and know her. That way when I see her I can talk to her whenever we are out without the hassle of everyone watching me or wondering how I know her.

Here is my other concern. I met her over the Internet out of curiosity after learning about Katoeys on a trip I had to Thailand about five years ago. Over the years I surfed the Net here and there and then I found her. This brings me to my next hurdle. She is in the adult industry. By that I mean that she has a website and she is an escort (to a small, discreet client base). I have to accept that part and so far I am doing just fine but the what becomes real difficult is that it would be that much worse in explaining it to my friends and family. Assuming I got over the initial TS reaction from them. Do you have any suggestions as to how I should handle this relationship?

Ask yourself, is it any of their business whether she is TS? Is there some reason your friends and family need to know that? Telling them could well create more problems than it would solve. Insofar as how you met, agree on a story and stick to it. You responded to a personal ad, you met at a club, you met at a restaurant, you met at a sports event, whatever.

Regarding her website and escort job, again, is there some reason they need to be aware of that? For all they need to know, she is living off an inheritance or is supported by family overseas.

Normally I wouldn't recommend one tell lies, but in this case it might well be the way to go as you are risking rejection by friends and family.

Many relationships have begun in our free transsexual chat. This is the best, most popular free transsexual dating and relationship chat in the world. Check it out today!

Join our mailing list! We will not spam you, no worries.


Subject: it's me again help
Date: 11/2/2003 12:32:49 PM Pacific Standard Time
From: Deleted
To: Deleted

My boyfriend he is 10 years younger than me want to marry me after I told him I'm post-op transsexual. Should I go forward? He has a daughter, she calls me "mommy," that makes me happy. Also my boyfriend told me his child is my child and he'll stay with me forever. I'm 39, my boyfriend is 29. Should I go forward to marry him?


Sounds pretty good so far. Marriage is a very big step. Do you love him? Are you very sure he loves you? Have you two known each other long enough to know each other very well? Only you can decide. Good luck to you.

Subj: Jane
Date: 9/6/2003 9:01:32 PM Pacific Daylight Time
From: Deleted
To: Deleted

Dear Advisor,

I am a mature transgendered woman and I have, finally, resolved my questions and fears of my sexuality and now ready to date. I cannot find the spot to meet men who are willing to see me and not my gender. I would like to date and have a seemly normal life, that is not to say there is such a thing, but you understand. I went to y'all's chatroom but I was the only one there, rats. Can you help me in my quest? I am a nice girl and have a regular job. I work as a master carpenter with a group of men and they totally accept me as "the girl." Please advise me as where to go. Thank you for for time and consideration.


Like it or not, gender is going to be an issue. Many men seeking a GG will be very put off (or worse) to discover on a date that you are a pre-op TS. I suggest you visit TG clubs, and also avail yourself of online dating services (such as match.com), and in your ad be up-front about the fact you're TS.

And if you were the only one in our chatroom on your visit, that was a rarity. The room is often quite busy. Try again. Good luck to you.

Subj: Article Feedback
Date: 8/24/2003 3:52:53 PM Pacific Daylight Time
From: Deleted
To: Deleted

I am very much in love with my boyfriend. I always believed that he was bisexual, but whenever I would ask him he would deny it. Upon reviewing his computer history files, I learned that he has a membership with a black TS sex site. He visits the escort section the most. He has also responded to all four of the TS girls listed in the New York City section of your site. I believe he has had sex with at least one TS recently.

He once confessed to having had a sexual experience with a shemale before we met. He has emailed gay guys invitations for sex as well. My problem is we are constantly making plans for the future. He proposed (although I declined for obvious reasons), we are looking at buying a house, named our first-born daughter, etc. So my question is, what are the odds of him waking up 10 or 20 years down the road and telling me that he is gay and that he wants a divorce? Is this a phase that will pass? He is 33.

--Confused GG.

How important is monogamy to you? It seems to me this guy is not ready to be in a sexually monogamous relationship.

Subj: Men
Date: 7/3/2003 7:43:12 AM Pacific Daylight Time
From: Deleted
To: Deleted

I want to ask something of you. Please help me understand men. I've been coming in your TS chat room now for a little over a month. I've met so many really nice guys, but the problem is that I meet them, we talk, we meet, and after one or two dates they want to move into an exclusive relationship. I explain up front that I'm looking, and I want things to go very slowly. They agree, then suddenly things change. I'm then being pressured to make a decision to see them exclusively, and stay out of chat.

What's the deal? I'm up front with what I'm looking for, and explain in depth that I must feel chemistry, as do they, for it to move forward. I never call them, and I don't email them except to answer theirs. I guess I assume all people are like me, if someone is not interested, so be it, I move on, lots of fish in the sea. I'm obviously doing something wrong here, and I would truly like your opinion as a man.

The big thing is, their behavior scares me off. In one situation, if this guy had not gotten so pushy and intrusive into my life, we could have formed a real friendship, which could have possibly led to a relationship in time. Now as it stands, I want nothing to do with him. Please give me some insight.


My guess is that it is very difficult to actually be able to just talk to a TS like a regular person, much less be able to actually go on a date with one. Also, I suspect, the guys you have met are very aware there are a whole lot of others out there who would like to be in their position. Hence, they feel an urgency to lock you into a committed relationship and don't want you even chatting online with other would-be suitors.

The guys need to chill out and proceed at a pace that YOU desire. They need to get past their fear you might find someone else. What they aren't seeing is that most every other guy is going to make the same mistake with you. So the advantage goes to the man who can relax, just enjoy being with you, and let things develop naturally. Also, I would suggest you add one detail to what you tell them up front about going slow. I recommend they be made aware that engaging in a rush to commitment will result in your dropping them.

Subj: question
Date: 5/11/2003 7:29:43 PM Pacific Daylight Time
From: Deleted
To: Deleted

As a straight guy with friends and family who might not be supportive or understanding about having a TS girlfriend, how does one deal with this issue? While I understand the fact that it's no one's business but ours, there is always the issue of getting her "clocked," etc. It may be reasonable to say, "If your friends don't understand, they shouldn't be your friends." But what about family?

My girlfriend replies: You face one of the toughest issues a TS or her boyfriend/lover ever faces -- family! Unfortunately there is no easy answer, but you already knew that or you wouldn't be asking the question.

First and foremost, I would hope that you have a feeling for what their reactions will be, what they can handle and what they can't. If they have met her and like her, that certainly would make it easier, too. The fact that they love you and that you love her would also help them deal with this issue.

There are a number of approaches: 1. Say nothing and hope no one notices. 2. Face the issue upfront, head on and let the cards fall where they may. 3. Feel them out on the issue first without letting on she's a TS, then decide how to best handle it. But no matter how you decide, what it will all come down to is they will either accept her or they won't. If they don't, then YOU have a very hard choice to make, her or your family.

Should the outcome be something less than perfect, remember people have the capacity to change, especially when they love you and you love them. Show them the love you have in your heart for her, even if it takes a while, the chances are good they will eventually accept her.

This may not be an issue with your girl (you did mention her being "clocked"), but I'm throwing it out for what it's worth. I was once told that what you project from inside you into the world is what the world will see. Taking that to heart when I discovered I was a girl, I decided from the very beginning that the female inside me would be projected into the world.

Despite how I looked, especially at the beginning, I was confident in my womanhood and I let that confidence show whenever I went out. Surprisingly, it worked! The world saw a person confident in her female self and accepted me from the very beginning. Lucky? Sure there was some of that but I truly believe that the confidence I felt in my womanhood is what made it all work.

Subj: advive
Date: 4/27/2003 10:48:43 AM Pacific Daylight Time
From: Deleted
To: Deleted

I am a divorced black male living with my 17-year-old son. To make a long story short, I have been dating TG women for almost 18 years and have had a few relationships in between. The problem now is, although my son is aware of who I date (I don't try to hide it from him), I feel that since he is close to graduating high school next year and will go to college, I don't want to bring my current relationship home. His education and mental well being is important, so is that of the woman I love. She really wants us to move in together and so do I, but I feel that my child's needs come first. I am in love with her and wish to continue our relationship. Currently she is on hormone replacement therapy and when she takes her weekly shots, her emotions run wild and she says a lot of hateful things. It is after her shots that she gets very upset (separation anxiety) and says a lot of hateful things. I have discussed this with her and she blames her hormones. We are fine other than the once-a-week shots. Please help.

Girlfriend says to stay away from her when she is in one of those moods, or consult with her doctor about adjusting the dosage. "She shouldn't react so badly," she said.

Subj: No Subject
Date: 4/26/2003 5:50:40 AM Pacific Daylight Time
From: Deleted
To: Deleted

Oy, I'm not sure where to start. I'm 19 years old and I live in Florida. I'm a pre-op TS that's pretty new to all of this. I've been trying to find someone to date for the longest time it seems like, but most of what I've found are guys that are way older then I am. It seems like most men who have considered dating a TS are far older, and the ones who aren't are just totally hormone-driven sex fiends in their 20s. Most guys my age either A. Don't know how to react when they find out, don't really know what a relationship would entail, or B. Haven't even figured out what they are yet. It's not that the older men that I've met aren't good guys, but I may be young and naive but I do have morals. I don't want todate a guy that was in high school when I was born (ha-ha). Am I just out of luck for the next few years 'til I get older? Or am I just not looking where I should be? I just don't know what to do anymore.


It's a real problem. There must be somebody for you, so all I can really do is recommend putting yourself out there for him to find you. You're an AOL member, use their personals section (keyword: love, put your ad in women seeking men). You've got a listing here too, which is good. Also, consider referring the hormone-driven guys your age who contact you to this website to learn. Your new man might be among them. Hang in there, girl.

Subj: re: advice
Date: 4/23/2003 6:06:22 PM Pacific Daylight Time
From: Deleted
To: Deleted


I find your editorials very helpful and I have been interested in TS's for about two years now. It is because I can connect with them easier than GG's. But I do run into a problem and I want to ask you this. I am 5'6" tall. Or short, depending on your point of view. I see many ads that seek the attributes I have, except this one. I have recently met one online and talked to her on the phone and we both are seeking love, something long term and a life in the country. I haven't told her my height and she is 6'. How soon should I tell her? I am really afraid (due to many no responses) that she will drop me. Please help. Thank you.


You do have to tell her, and it should be soon. You've spoken on the phone, hopefully several times, and you two have had the chance to develop a rapport and friendship. If she really likes you, it's because you're you, not because of your hair (or lack of it), or height (or lack of it), or money (or lack of it). Bear in mind that she has her fears of rejection as well. She's six feet tall, way taller than most GG's and taller than most men. If she's rejecting men strictly on the basis of height, then she is making a mistake.

Women appreciate honesty. They want to know what you really think and feel. You have to trust her judgment and trust in her desire for honesty in a man. If I were in your situation, I would tell her how I feel about her. That we have things in common, such as a love of country life. I would tell her I am very interested in exploring a possible relationship with her. I would also tell her that I know that she appreciates honesty. And that she needs to know something about me that has been a problem for some other women (right now, she's thinking, "Oh no, he murdered somebody.") Then I'd tell her how tall I am. If there is a long pause, I'd crack, "Hey look at it this way. I'll always be looking up to you." If it is an issue for her, then you have the chance to talk about it.

If she's concerned about how others will view you as a couple, there are a couple ways to go. Those who comment can be ignored ("It's none of your business") or she can slap 'em around some ("He's short but the best fuck I ever had.") It's amazing what can be accomplished with a sense of humor.

If you don't make a big deal out of it, odds are she won't. If she rejects you over your height, then you were talking to a pretty shallow girl, or a foolish one. If you get rejected, send her this URL and tell her to read your letter. She might rethink her actions.

Subj: Advice?
Date: 4/10/2003 11:26:29 PM Pacific Daylight Time
From: Deleted
To: Deleted

I met a TS almost two years ago and dated her on and off (she has one more surgery) for the past year and a half. I found out last month about all of this, I was in the dark and always thought of her as a woman. Admittedly, I was out screwing around with other girls, so I wasn't real serious about her. When (a few months ago) I thought I may want to get serious, I paid more attention to what she was saying and caught her in some lies.

Like I told her, little lies lead to big lies and well, I uncovered it all through a friend and my own research that there was a switch made. After the initial week or so of rage, I am trying to take a different road and trying to understand this person. I guess what I am asking you is, what is thought of about a person like me? A stereotypical guy, beer-drinking, sports-playing, skirt-chasing, that has had this happen to them?

I care about this person, and I know she is totally into me, speaking of a future and living together and life "after everything is done," but I do not know how to feel. Any advice or comparisons would be appreciated. I am a big enough person to ask for this advice and not let it rule my decision. I just have no one else to ask.



Well first off, she should have told you. Not to do so is a personal safety risk for TS's. Beyond that, you two seem attracted to each other. It is apparent that you have been able to accept her as a woman in the past. Your anger is easily understood. What you discovered would be a serious shock to any regular guy. You ask what is thought of a guy like you. From here, you seem like a good man, and apparently she thinks so too. All you have to do is forgive her goof and enjoy her for who she is. And who is she? She's the girl you're attracted to. She's the girl who loves you. Remember, this is just a simple plumbing issue. She's been a girl all along in spirit and mind, and now her body reflects that. It's the girl in her you've loved being with. So enjoy.

Subj: Can I Ask Some Advice, Please?
Date: 3/3/2003 4:47:22 PM Pacific Standard Time
From: Deleted
To: Deleted


I met a TS girl recently via personals, and we started hitting it off very well, and were mutually attracted to each other. She lives one state away, and while talking, she asked if I'd like to visit her for the weekend. And so I decided to.

I got there, we still very much liked each other after meeting in person, and was honestly one of the best dates I've had in months (sushi for dinner, movie, talking, a bar, just great). The night progressed even farther, and we ended up back at my motel room. I guess she got a little too relaxed and (I apologize sincerely if this is vulgar), she ended up relieving herself on my bed during the act. Embarrassed, she wanted to go home, but we were going to do something the next day, and kissed good-night, so I didn't think anything of it.

The next day, I got up, bought her a dozen roses and chocolate, and called her to begin our day. Long story short, I was there in a strange town exclusively to see her, and she wouldn't return any of my calls, or pick up the phone all day long. I stopped by her house, and left the flowers there on her door. A few hours later, I stopped by again, and the flowers were taken in. But still no call. And I was faced wih the realization that the entire reason I came to this town suddenly just dropped me. I spent a very boring and empty evening alone in a small town before I returned home the next day. I've been miserable all day (and the majority of the weekend) trying to figure out what to do, or even what exactly happened. I would be very appreciative of any advice you can offer on either how to close and heal the the communication gap between us, or even help me put this into perspective so I can deal with this easier.


As my girlfriend points out, who really knows what goes on inside the head of someone else?

Let's get to the bottom line here. The accident might or might not have been accidental. There is the possibility she did that as a means of justifying cutting off further contact. Some girls just don't know how to say "I'm not interested." She knows you're interested and has deliberately chosen not to reply to your calls and messages. Take her lack of response as the message. If she changes her mind, she knows how to reach you. So, now, it's time to move on. Good luck.

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