Dating Advice for Trans Men (and everyone else, too)

Recently another trans man reached out to me. He asked how he could safely date and meet someone who he liked and who also liked him. (Yes, you are reading that correctly, someone came to ME for dating advice!) The truth is, dating isn’t easy for anyone, unless you’re extremely lucky—in which case, I hate you. The truthier truth, and I’ve said this before— is that dating while being trans is even harder. It adds a whole other layer to it. And it really shouldn’t. But it does because there’s transphobia, gender norms, internalized transphobia, etc.

Fear is where the difficulties begin. A fear of safety. A fear of rejection. A fear of being shamed. A fear of being vulnerable. Will I be safe going on a date with a stranger? How will this person react to finding out I’m trans? Should I tell them ahead of time or should I wait to see if there’s a connection before I put myself in a vulnerable situation? Is there a safe and/or unisex restroom where we’re meeting? Does this outfit make me look manly/womanly enough? If I do come out, how do I and when do I? The questions and anxiety continue.

I’ll be honest—I’m not sure I have a great answer for this question. I quickly begin to sound like all of the married friends or friends in long term stable relationships when they try to feed me (unsolicited) advice about dating. Here’s what I do know.

Lead with authenticity. It’s the hardest and most vulnerable thing you can do in life. But it will also be the most rewarding. What do I mean by this? For example, whether you tell a person you’re going to date ahead of the first date or on date three that you’re trans is your choice. Neither choice is more right or more wrong. If it feels more natural to you to let someone know from the beginning because nobody has first and second dates to waste on someone who is a bigoted jerk face? Then share it from the beginning. If you want to see if there’s a connection first before you share something extremely personal and vulnerable? Then wait until you know you’re interested in seeing this person again.

Another good example is around gender presentation. Don’t over-concern yourself with trying to be super masculine or super feminine to fit perfectly into a gender role. Act like yourself. I remember when I first started dating after I began my transition. I was really worried that I wouldn’t be seen as a “real” man. I tried to overcompensate and spent way too much time thinking about ways to fulfill gender stereotypes so I could fit in as a guy’s guy. But that’s just not who I am. Before I came out and transitioned, the world saw me as a super masculine woman. And now suddenly the world sees me as a slightly feminine man. I act the same, for the most part, but the world has different expectations for men and women so the perspective changed. I don’t want to play pretend—I transitioned so I could finally be myself, not to turn into Thor.

Try, try, and try again. We can’t all be Cory and Topanga and find “the one” in middle school. I think loneliness, a feeling of hopelessness driven by insecurities and self-doubt make us consider settling. You deserve better than to settle. You aren’t dust, you don’t need to settle, you’re a phoenix that rose from the ashes—or some other inspiring metaphor. Listen, my point is that you’re bound to have some terrible dates, some mediocre dates and some incredible dates. Be like Goldie Locks, search and find the just right, don’t take the too hot and too cold porridge just because it’s available. And DO NOT get out the rolodex of exes. You’ve been there and done that and in the majority of the cases not enough has changed to give you different results.

Remember that your worth is not measured by whether you are single or in a relationship. I know it’s hard on a Friday night, when Facebook and Instagram are both telling you that everyone you know is coupled up AND they are always so happy and so cute you could puke. Meanwhile you’re pouring another glass of wine while you watch Netflix, alone, reminding yourself that you are technically not alone because Fluffy is sitting next to you, grooming herself. It’s hard to remember that when those couples aren’t posting cute pictures they are probably arguing over who’s turn it is to clean the toilet. Or they’re in separate rooms in the same house because they desperately want the alone time that you are cursing at this moment. It’s difficult to feel affirmed as beautiful, funny, smart, and worthy beings when it’s up to us to give and receive validations. And on top of that as trans men, we have heard over and over again through the media, the stranger at the shell station, maybe even some of our friends and family, that we are freaks not worthy of love. It’s hard to not have some of that sink in and consume the way we see ourselves. Especially when we’ve come home from another bad date. It begins to feel like we’re going to be alone forever and being trans put the nails in that coffin. But it didn’t.

Being trans and making the brave and bold choice to be true to yourself made you even more dateable. Because now you are able to be your authentic whole self and that means you have some of your authentic whole self to share with some lucky person. And until you find that lucky person, celebrate you. Fill out online dating profiles, swipe left and right, ask friends to set you up with (quality) people, smile at someone at the grocery store, make small talk with the cute cashier at the pet store, and maybe one day you’ll be thinking of bad advice to give another single trans man.

Most importantly, remember that you are a brilliant, magical, bold, and handsome stud muffin who worked too hard to get here to not lead with authenticity with that best foot forward. Now go look in a mirror and tell yourself, “I’ve got it going on.” Do it. Because this (self-proclaimed) relationship expert told you to do it.


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