Former Escort and Post-Op Transsexual Wants Her Understanding Boyfriend to Be More Ambitious.

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!


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 4½ 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.

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  1. 1

    You only forgot one fact – she also needs to love him – otherwise those good points you mentioned:

    “he 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.”

    are totally non-issue, as she starts feeling suffocated, and unworthy of his feelings.

  2. 2

    When it comes right down to it, I think the important thing is L-O-V-E. Do you love him? If you love him, accept him — flaws and all and make yourself responsible for your own happiness. Make the money that you need to make, experience the places that you need to experience; even if you have to do it individually. If you don’t love him, move on — no matter how scary it may be. Yes, there are many judgemental people in the world, but there are also a surprising number of nonjudgemental people. The right one may still be out there waiting for you. Just my two cents. 🙂

  3. 3

    Thanks, Lysette, for writing. It’s definitely a thought-proving question. I have no advice, but just had a few questions for you.

    During your dating days, what percentage of men accepted you for who you are (including your past)? Did any?

    Do you want a lifetime relationship, or are you happy with just dating someone for a while?

    Have you tried suggesting some more “worldly” activities to your boyfriend? How did he respond?

    Are you happier with your boyfriend, or by yourself?

    If you found that though not every guy was willing to date someone with your history, there was a decent enough pool of guys that would then you might be inclined to try your hand elsewhere. But I just want to caution you that someone’s willingness to date you is not necessarily the same as their willingness to marry you. (Some of the discussion on the Women are Racist thread might illustrate this point). But if you’re not interested in marriage then again, that opens up your options.

    If you haven’t suggested activities more to your liking to your boyfriend, then I suggest you do so. If he isn’t willing to try them does he care if you go out with friends and do those activities? And do you care if you’re still able to do those activities, but he chooses not to join you?

    And my last question is probably the most important. If you’re happier by yourself than with your boyfriend, that’s a definite clue that you should leave. But if he makes you happier, then the question becomes are you willing to risk not having that additional happiness in the hopes that you find someone else more stimulating who also accepts you the way you are.

  4. 4

    Great questions and things to consider, A-L.

  5. 5
    Mikko Kemppe - Relationship Coach

    Great answer Evan!! I agree, in the end you can only listen to yourself and follow your heart! That is if you choose to believe that your heart and intuition will guide you in your journey! I wish you the best also!

  6. 6

    It is unfortunate, of course, that not that many people are actually enlightened enough to be non-judgmental. It is indeed true (from what I observe, anyway) that most of the non-judgmental folk are those who are in the least demand. They are simply in no position to be picky.

  7. 7

    Surprised more people haven’t commented on this one.
    28-year-old guys are usually huge dumbasses and often paupers playing video games. If your guy is solid emotionally, non-judgmental, kind, etc, then you’ve got a great foundation. He’ll probably turn out to be a real gem by the time he’s 33 and may even start moving up the social ladder. I’d suggest keeping this one. That’s almost the best you can hope for with dudes age 20-30. The fact that he accepts you is, quite frankly, remarkable. You won’t find that anywhere else.

  8. 8
    Karl R

    Lysette said: (original post)
    “sometimes I feel I deserve someone who is a bit more worldly or has more life experience.”

    Dating isn’t a meritocracy.
    Great partners don’t go to the people who “deserve” them most. The same is true for almost every other aspect of life as well. When you try out as an actress or model, does the casting director ask you why you think you deserve the role? He doens’t care. He’s looking for what he wants.

    What you deserve is irrelevant. What you want, what you need, and who you can get … those are relevant. I’ve always assumed that I could get someone who as good as the women I’d previously dated. She wouldn’t be the same. She would be better in some ways and worse in others. And that has remained true for me.

    I can get everything I need and most of what I want. I don’t know whether you can get what you want in addition to what you need. But your ability to get both has nothing to do with what you deserve.

  9. 9

    I have to agree with Lance, though (and thus expose my own lack of enlightenment) – I am actually surprised you were even able to be promiscuous! I mean, unless you really look feminine, and you simply don’t tell your partners that you used to be a man, I think at least 99% of men would be totally freaked out by that!

    Or am I way off in my estimate?

  10. 10

    Hi Lysette, I am an ex working girl myself and have experienced a similar side to life as yourself. I’m sure we have similar stories. The thing is, when you have worked in the inidustry, you feel wonderful and stimulated on most dates as the clients can often be interesting, funny, rich, successful men. Every session leaves you feeling like the first date with a new guy. Then when you quit and step into the real world, it’s not the same. I currently have a reliable, secure, boring, socially inadequate guy, but he loves and accepts me for me and my history. Often times I question do I want this, he is boring, i want more from a guy. But then I think about the scenarios of the fake connections I had with clients and put it into perspective. Just as Even says, looks fade and it is difficult to find guys who are ok about our past and love us. But then at the same time we will always hanker for that excitement. We won’t get that excitement hun. We have experienced something very different and we expect more. In reality, people who have not done our types of work and lifestyle and have ‘normal’ relationships are happy with the simple things in a relationship. As someone else also suggested, you can help him to grow and become more fun, I am doing this with my guy. Your guy trusts and loves you, why not give him the chance to grow and make something wonderful out of your foundation together. If he truly doesn’t want to work towards developing then you need to poss re think about what you need. Be careful tho, we share different life experiences and expectations than the average woman hun. xx
    PS, Evan, your response has just turned everything around for me. It all makes sense now. Thank you xx

  11. 11

    He’s succeeded completely in becoming an woman and this is never satisfied.

    @Lucy.  Your point of view is not often heard when discussing your former profession.  Adrenaline is addictive.  Yes?

  12. 12

    Its good that Lysette has resolved her physical issues before she thought in terms of a finding a life partner.
    I made the horrible mistake of getting involved with a tranny chaser close to the start of my journey.
    I am a pre-operative transsexual and probably won’t have my gender reassignment surgery for a few years yet.
    However, it does sound as if Lysette is looking her boyfriend as a work in progress who can be fixed.
    That’s not good. Either love him as he is or leave him alone!

  13. 13

    that post op hypergamy too strong. she should leave him and look for her perfect man so he can move on with his life and find someone who accepts him unconditionally, like evan suggests women on here to find.

  14. 14

    I had to call a female friend of mine and show her this letter from the OP because is was practically her life at a point in time. Her ex husband was a bus driver as well and she was upset about his lack of ambition. She wanted him to go back to school so that he could get a better job. He begrudgingly agreed to do so, but had a lot of difficulty with his classes and decided that he didn’t want to continue. At the time she told me that she felt like he was lazy and kind of dumb and said it was sad that all he wanted to do was drive a bus.

    His side of the story was that he loved his job as a bus driver. He genuinely enjoyed going to work each day, driving, meeting new people and continuing conversations with regulars. He said that the drivers received a dollar an hour raise each year. He was making $15/hr., so if he stayed on he could double his salary in 15 years. While many wouldn’t consider that ideal, it still sounds like there is at least some ambition there. And he is fortunate to be of of the few that  get to actually enjoy going to work everyday. I didn’t think that is was right for her to try to get him to leave that just because of her personal feelings on the matter, while having no regard for his.

    If he likes his job and video games, and he liked them 8 months ago, I don’t think you should try to get him to change. But maybe you could talk with him about compromising – more date nights more often, with a wider range of activities. In return you could play some games with him or just let him have game night if you aren’t interested .

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