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Dating a Transwoman: My Adventures & Some Advice.

By- MichaelTSG

What in the world is the problem? You want to date a transwoman, and one placed an advertisement on some transsexual dating site, along with a picture. You responded politely and respectfully to her ad. You told her about you and what you're seeking.

You even sent along a nice, current photo of your charming self.

She and you seem to be a good match. Based on what you see in her profile, you seem to have similar values and interests. Your goals line up well. You like her pictures, and you hope she likes yours. If you're like most guys, you're no Brat Pitt but you also don't frighten small children and dogs.

And she ignores you. What the heck? (This happened to me several times.)

The promising coffee date

Or maybe you two did meet for coffee or lunch. She's got this great smile and eyes that sparkle. You notice that she's got a sharp mind and a quick wit. You love her svelte shape and more-than-ample boobage. Knowing transsexuals as you do, you expect they're implants, but that's no matter.

She raises the subject of transsexualism and specifically mentions that her boobs are not implants, but the result of hormones. Wow, that's very cool. Hooray for hormones!

You think to yourself, This one has possibilities! You leave the coffee shop together and go to a movie. The movie was great. And on the drive back to her car, you talk about it then the subject changes to her life. She tells you about her background and you're listening attentively.

When you get back to the coffee shop where she left her car, you give her a light kiss on the lips and a hug. She's a definite participant in this goodbye ritual. She says she wants to see you again, and then you part ways. Later on, you email her and tell her -- and you're serious about this -- how much you enjoyed meeting her.

The rude shock

A couple days later, she emails and says to forget it, that you're an overcontrolling, insensitive man. Again, what the heck? (This also happened to me.) You think about this for a while and write her back. You politely defend yourself because you don't think you're an overcontrolling, insensitive jerk.

You remember back to all the times your prior girlfriend said, "I'd like to spend Saturday shopping for clothes," and you said OK. Prowling Macy's and other stores isn't as much fun for you as a NASCAR rally, a hike up a mountain trail or seeing Avatar for the 10th time, but you'll happily do your part for your girl.

In the stores, you were an active participant. You have a good idea of her taste in clothing and you know what you like to see on her, so you shop also, instead of sitting on the "husband bench." When you find something you think she might like, you hold it up for her to see and decide about. So you think, Is this the behavior of an overcontrolling, insensitive jerk?

You say to this woman you went out with that you feel her judgment is premature and in error, but you also say goodbye since it's unlikely you'll ever hear from her again.

Welcome to the insane world of transwoman dating. Or of any kind of dating, for that matter

You may not be to blame

Bear in mind one detail when you're seeing someone over age 30. By that age, most of the single ladies you meet have been married and divorced or have been through other major events (in the case of transwomen, transitioning) that could result in some severe emotional baggage. Single people over 30 have scars.

There is a good chance they are single for a good reason. In other words, don't be too quick to think the problem is you. Other boyfriends may have walked out over issues she has.

Or, she may enjoy being cruel. If that's the case, this girl has huge problems you don't want anything to do with. There's no shortage of sadistic monsters online. Adolph Hitler may lurk behind the sweet, smiling face of this transwoman you tried to date.

See, this is why it's good to be in a relationship! You have someone you can have fun with, someone you can trust, someone you can talk to, someone to mess around with in bed and whose body you know, and someone who isn't freaking nuts. Hopefully.

(However, if you repeatedly get criticism about your attitude, behavior, appearance or hygiene, then be aware you have an issue that needs to be addressed. If you're not sure what to do to improve matters, consult a therapist or your Mom, or take a shower and use soap this time, or mouthwash, whatever.)

(If you're overweight and that's an issue for the ladies you've been seeing...well, everyone knows what to do about that problem. Diet and exercise. Get to work. If it's a drug or alcohol problem, there are organizations that can help. If it's cigarettes, there are online and real-life support groups and products to help you quit. If you really want to quit, then quit.)

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Approach personal ads with caution. You don't know this transwoman advertiser. She may be misrepresenting herself. What she put in her ad may be some fantasy that she has about herself and it may bear little resemblance to reality. I know one transwoman who placed a misleading personal ad. She used a fake name and posted her age as 10 years younger than I know her to be. She really believes that she looks that much younger. Guys will agree with her just because they want to get into her panties.

The truth is, her photographs required work in Photoshop to erase or diminish deep lines and lots of wrinkles. The truth is, she looks her age. Don't believe your own propaganda, people.

Some personal ads that you're looking at may not be sincere. Maybe that sweet-sounding transwoman who is looking for love is actually looking for money, property or a way to escape poverty, such as in the Philippines. Keep your wits about you in the early stages. If she's asking for favors or money, walk away (unless you don't care and have cash to burn.)

When it comes time for the first meeting, invite her to lunch or dinner at a nice restaurant. You can suggest a place, but since women are the ones who get pursued, let her choose where to meet. Safety will be on her mind. With any luck at all, you will have a fun conversation and be able to share experiences, and will part on a positive note.

Immature mind in a mature body

But if you get one of those post-date turn-downs (like I did, "overcontrolling and insensitive"), and if you genuinely feel she's off the mark, don't take it personally. There is one big issue with transsexual women that's addressed elsewhere on the TSGirlfriend.com website. Usually, transwomen were not raised as women. In most cases, decades will pass before transitioning, and so you may be dealing with, say, a 40-year-old woman with the expectations and experience level of a teenager.

Over the years, I have encountered many TS's who possess unrealistic expectations and who are way oversensitive to some things when compared to natal females. Their feelings and beliefs have not yet been tempered by experience and the passage of time. They were not raised by women as women and thus lack perspective. This lack of maturity can easily lead to making erroneous judgments, and thus to unhappiness.

The "princess syndrome" is a good example of immaturity, and I have run into this a few times: "You must cater to my every whim else I shall pay no attention to you." Oh lord, give it a rest. What mature man wants to date someone who acts like a freakin' 14-year-old girl? A worthy response to that would be: "Hannah Montana is on and you're missing it."

Men are lunkheads

Really. We truly are. Most of us have a clue as to who and what we are, but generally we don't dwell on the philosophical aspects. We don't intellectualize it. There's an old joke that says all men want is beer, football, food and sex. To some degree, that's true.

We like what we like, and we don't like what we don't like. Women can find out everything they need to know about men in the Mars/Venus books by Dr. John Gray. We are simple creatures. Most of us don't have a high tolerance for stupid bullshit. When a woman slaps us with the likes of the princess syndrome, we roll our eyes and leave. And then the princess sticks the blame on us for not recognizing her oh-so-special qualities.

We may be lunkheads -- it's a genetic guy thing -- but we aren't stupid. Most of us recognize bullshit when we see it.

Transwomen should be mentored by genetic females in the ways of femininity, not by other transsexuals, and certainly not by so-called "transgender women" (read: cross dressers.) Doing so will who only serve to reinforce their unrealistic expectations. I'm laughing as I write this. The question that came to mind was: "Do you want to be a woman or a parody of a woman?"

If you're routinely failing at relationships, look inward.

Identifying important qualities

If you put a 40-year-old genetic woman side by side with a 40-year-old transsexual who transitioned five years previously, I assure you the genetic female will have a better grip on what she considers important in a man, and will be far more successful at identifying those qualities.

If you're quite sure there's nothing going on with you that would justify a negative response on the part of a transwoman, it could be a simple lack of chemistry. Or maybe it's bad judgment, immaturity or "Unknown Factor X" on her part. Just move on. If it's any of the latter, most likely, she has lessons to learn, and unless she's asking you to teach her, you'll be better off with someone else.

Remember, she may be single for a very good reason!

Copyright 2010, by the author, all publication rights reserved.

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The topic of this page is dating a transwoman, some adventures and advice..