What It's Like To Be Over 30, Transgender, And Looking For Love

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What It's Like Looking For Love While Being Transgender

If you're a woman in your mid-thirties, the dating scene is challenging enough. You're conscious of feeling older, as wrinkles become a reality and you feel like your stock value as a potential wife is plummeting. So in the past year, I decided it was high time I met a fabulous man.

In my good moments, I feel quite fabulous myself. I feel like an attractive, successful, and snarky strawberry-blonde who cooks like a dream and has a joie de vivre ... unlike most. I was open to meeting all sorts of men. But, there's one thing that sets me apart from other women my age — I'm transgender — specifically, I'm a transsexual woman.

In short, I've always felt like a heterosexual woman. Before surgery, I was attracted to men. But, unfortunately, I also looked just like them. While the topic doesn't pick up as much shock value as it once did, I assure you that a very powerful stigma remains for those who are transgender.

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It's created some emotional baggage (which, let's face facts, we've all got). The thing is, I struggle with my own pain and shame that feels especially sharp in relation to dating, relationships, and sex. 

So while I had hope and assumed I'd eventually find a like-minded guy who would appreciate me for me, it didn't work out as easily as I'd envisioned. 

I truly wish I was divulging to you that holding my head high, I summarily rejected each man who clearly wasn't worthy of my love, time, and energy. But to be completely and painfully honest, I gave each multiple chances. I cut guys more slack than most anyone I know. For many reasons, including the secret hope that I clung to — the hope that each of these men would do the same for me. Because, I, like anyone else craved a genuine love to call my own.

Yet, the fact remains, it's impossible for me to ignore my history when it comes to sex and relationships. I know that the only path to true love is truly loving and accepting myself — and that means being able to be fully open and honest with everyone in my life, including dating partners.

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While I've dated several men — many for just a few weeks, some for a few months, and one (my first love) for over a year — none have ever been worthy of knowing my truth. And, frankly, it's me — it's because I'm terrified. This is the same fear that has paralyzed me all of my life. The very obstacle that caused me endless tears through my first five years of therapy.

Because the fact remains that the biggest hurdle I faced when I decided to become a woman wasn't going under, while a surgeon turned the parts I was born with inside out. It wasn't learning to own and operate my brand-new, $25,000 anatomy.

It was the bloodcurdling fear that correcting a glitch and becoming who I already felt like I was on the inside subjected me to the possibility that I'd have to live without love. 

I thought I had overcome this obstacle years ago, but sadly the fear persists. And I wish I could continue writing about how I have overcome it. I wish I could write further about how I solved my dating struggles. I wish I could say I was able to create an opening in my life for a fabulous relationship that's enduring and sustaining. Yet, I am left with this horrible pit in my stomach.

Intellectually, I can see how it would be possible for me to find a partner who is open-minded and fully accepting. Emotionally, I'm still working my ass off in therapy to get there because the questions that linger won't stop churning away. 

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Do I belong on the Island of Dating Misfits? Am I doomed to either superficial, short-term relationships — relationships that force me to keep my history a deep, dark secret — or a life of lonely spinsterhood? I'm not positive, but I can only hope not.