After a mentally abusive relationship, and a lot of bad dates and or one nighters… I got to a place where I stopped looking to be in a relationship and just enjoyed being somewhat promiscuous and enjoyed being single in the Manhattan dating scene. Over a year ago, I met my current boyfriend, who at the time, was nothing more than the guy I called when I needed a warm body next to me at night. After our strictly physical relationship became more routine (in a good way), I began to see what a beautiful and simple, kind, loving man he could be. Here’s the twist… in addition to being so sweet, he is also understanding. I decided to reveal my past to him and explained that I am a post-op transsexual and let him know that if he wasn’t comfortable with my past then he could go on his way and I would as well…

Long story short, he accepted me and eventually we took our relationship to the next level and we have now been living together for 9 months. He accepts me and my past more than any other man has, but the problem is this… I feel he lacks ambition and even a certain amount of social skills/intelligence at times and it bothers me. He’s a simple, loving, non-judgmental creature who drives a bus for a living and plays video games when he has free time. Occasionally, we will go out dancing, but that is the extent of our activities. I’m 28, an aspiring actress/commercial model, ex escort/stripper. I have lived more in my half a lifetime than some ever will, and sometimes I feel I deserve someone who is a bit more worldly or has more life experience.

And while you seem to have processed your past in a healthy fashion, make no mistake about it, you’re carrying a full set of Samsonite into any relationship.

But everytime I think that way I remind myself of my circumstances… my prior failures with men, my transsexuality and the fact that I can’t have children… and I snap out of it momentarily, only to be discontent again at a later date. He has brought up marriage and I shy away from it, but the thought of getting back out there in the single life and risking being rejected by men who may not accept me and my past scares me… I’m so torn. Please help!

Lysette

Dear Lysette,

Well-written, and probably the first post-op transsexual reader question I’ve had yet. Thanks.

So, to start off, I’ve gotta tell you: I’m torn, too.

I mean, it would be easy to tell you to keep him. You know how lucky you are to have found such a non-judgmental man in a very judgmental world. Hell, I come from Los Angeles and New York, where men break up with women if they’re 5 lbs overweight or didn’t get an Ivy League degree.

And while you seem to have processed your past in a healthy fashion, make no mistake about it, you’re carrying a full set of Samsonite into any relationship. Finding a man who loves and accepts both your transsexuality and escort experience is a tall order indeed.

Yet, it’s never a smart idea to do something just because it’s “safe”.

One of my favorite quotes is “What would you do if you could not fail?” Well, if you could not fail, Lysette, you’d be single once again, going through the dating process, and experiencing all of the ups and downs that come with it. You’d be doing so under the assumption that there is a better man for you out there, and that the search for that man would be preferable to staying in your current relationship.

As we’ve debated endlessly on this blog, there’s not a right or wrong answer – at least not until you look back at the end of your life. Which is why it’s impossible for me to tell you what’s right for you. We can agonize about this from every angle and still not come up with the perfect answer. After all, if you leave him, you risk never finding as kind a man. If you stay, you risk resenting him and always thinking you could do better.

Choices are hard when the answers aren’t black and white. I think you’re reaching out in hopes that I can share something that you haven’t contemplated yourself.

I doubt it.

Looks fade. Money comes and goes. Intelligence is hot, but you can get stimulation in 1000 different places.

But as a dating coach who has spent four hours a day, five days a week, for six years listening to similar issues, I might be able to better predict the pros and cons of your choices.

The question is what YOU can live with.

This brings me to a point I’ve long wanted to make here, which is that everyone gives advice from their OWN experience. Myself included.

Thus, the reader who “settled down” and found herself miserable and trapped in a dead-end marriage will warn every woman, “Don’t settle! You’ll end up like me.”

The dating coach who “settled down” and found himself ecstatic with his decision after making certain compromises will tell you another story.

All I can say is that, as I get older, and work with more clients, the more confident I become that nothing is more important than kindness and selflessness.

Looks fade. Money comes and goes. Intelligence is hot, but you can get stimulation in 1000 different places. The things that matter most when assessing a life partner is whether he/she loves you unconditionally, accepts you at your worst, and puts you first.

I have a client right now who has a wonderful 4 1/2 month relationship with a man. But even though she feels passion for him, she feels a bit uneasy. Why? Because no matter what an amazing man he is, he still prioritizes his kids and job before her.

Is it more fun to ride a roller-coaster than a steady train? Yeah. But there’s a price to pay, too.

And so she walks on eggshells, never knowing if this man truly loves her and will want to stay with her in the long run. Yet she left her last, devoted boyfriend specifically because she didn’t feel the excitement and inspiration she wanted to feel.

Once again, there’s not a right and wrong. It’s a tradeoff, pure and simple. My client gave up comfort and chose more excitement. With that excitement comes insecurity. Is it more fun to ride a roller-coaster than a steady train? Yeah. But there’s a price to pay, too.

You know what you’re facing, Lysette. You can give up this man and take your chances that you’ll find another non-judgmental man with a bigger brain and fatter wallet. Or you can stick with what you got, knowing that while you have very real issues with him, at least he loves you, flaws and all.

Your reservations are 100% valid and you’re not wrong for wanting to leave him.

You’re still young and growing, and it’s entirely possible that you’ll find another, more impressive man who embraces your past as your current boyfriend does.

You don’t know unless you try.

Alas, only time will tell.

I wish you the best of luck. Please let us know what you end up doing.