You Need Help: Should I Try Again To Turn a Friendship Into Romance?


Hi, I’m a trans masculine bisexual who has a problem with falling in love with my friends. When I first met my best friend, six years ago, I was madly in love with them. Butterflies, obsession — the works! I told them and nothing came of it, but we stayed best friends even with my crush complicating things. At the time, I figured the only reason I had been rejected was because my bestie had only ever been with cis gay men. That my trans body was the problem, like it had been in almost every romantic encounter I had had with cis gay men at the time. I know I was attractive to them, because tbh I look almost identical to their cis gay ex. And we were together constantly (I even lived at their house for two months!), so to me, the only reason we weren’t a couple, was my genitalia. It hurt, but we remained besties.

Fast forward to this weekend, I no longer have those butterflies, but we are very much soul-connected. While out at the club, they told me they had their first sexual encounter with a cis woman and were experiencing crush feelings. It felt like I had been stabbed with a knife. I always assumed that this would be my person if it weren’t for my body, but now it feels like a personal rejection. A rejection of me. And it hurts. Being rejected based on your body hurts a lot, but there is a slight cushion to the idea that it is out of your control. Or maybe it was a cruel twist of fate and we met at the wrong time? Or maybe now their sexuality is expanding and I have a chance? I don’t know if I can handle watching them fall in love or date this girl because… that should have been me… If that happens — how do I handle these feelings? How do I stay happy in this friendship if I start feeling jealous, protective, or resentful? And if they are expanding the types of people they sleep with… is it worth the risk making a move again?


Oh dear Letter Writer, I can practically hear the record scratch. I’m sure in your ears it was loud enough to drown out whatever music was playing in the club, that moment when the core assumption that had allowed you to accept your friendship with your bestie as it was came crashing down.

You write, “I always assumed that this would be my person if it weren’t for my body, but now it feels like a personal rejection.” The neatly organized narrative that you and your friend were incompatible on some immutable level outside your control kept you safe. It came apart at the seams when you learned your friend was open to being with someone whose body was like yours in ways you previously thought they would never be into.

Although this key assumption fell apart, I still see several assumptions driving your thinking. For example, you “know” he finds you attractive because you look just like his ex, but that assessment relies on a pretty superficial notion of attraction, which I imagine you know on at least some level. Attraction is much more like a cocktail than a shot. It’s a bunch of stuff mixed together in a nuanced way that is at least 50 percent inexplicable. I mean, look at all the debates over who is the hottest Hollywood Chris! I have, more than once, had a major crush on an identical twin while finding their sibling to be tolerable at best.

You assume that if your bestie is theoretically capable of wanting to date people with vulvas now, then not wanting to date you six years ago was a personal rejection. Of course, rejection is personal — how could it not be? It sucks. It feels bad. It is often completely not fair. But declining your romantic overtures was not a rejection of you as a person — as evidenced by the years of friendship, cohabitation, and platonic intimacy you’ve shared since then! Still, I think if they wanted to be with you romantically, it would have happened by now.

So, my first advice is to release these assumptions. If you can’t quite let them go, put them in a Tupperware container and stick them in the pantry. Close the door.

With those set aside, let’s get into it. I have to go out on a limb a bit and start with the big unnamed pain I read in your letter. I encourage you to take a look at the ways that internalized transphobia and perhaps even bioessentialism are affecting your sense of self-worth. Tap in a trans friend, a journal or other self-reflective tool, and/or a therapist. If I’m wrong and you were just being concise, all to the good, but it seems like you are holding onto some feelings and ideas about your body or your AGAB that are obscuring the ways in which you are lovely, worthy, and desirable. I wonder if you were projecting your own feelings about your body and assuming your friend felt the same way, that these feelings explained their rejection because they reflected something true and unchangeable about you. Of course it’s true that some people have preferences for certain bodily configurations, but your body is not inherently a reason for someone to want to be with you or not want to be you. Your body just is, it is yours to do with as you please and with the consent of all parties involved, and it is good — yesterday, today, and tomorrow.

Here’s what we know: Six years ago, you fell hard and fast for a new friend. You made a move, they weren’t into it. Despite the awkwardness of a lingering one-sided crush, you continued to build an incredible, soul-connected friendship. Now, your bestie has a new crush and it’s bringing up a lot of old hurt and insecurities for you. I have so much compassion for that. It’s painfully human to torture ourselves wondering why someone doesn’t want us the same way we want them, demanding answers from the fates, trying to pull apart the timing, the exact word choices, the deodorant you were wearing, all the details that added up to the sorrow of unmet longing. When your friend did the innocuous thing of sharing a new crush with their best friend, I imagine they had no idea of the journey they were about to send you on.

It seems like you’re vacillating between internalizing their new crush as proof that something is wrong with you and hoping it means there is a chance to add a romantic or sexual dimension to your relationship with your bestie. If I had to guess, I’d say neither is true. As covered above, one person’s non-attraction doesn’t truly say anything about you at all. And, unless you’ve left out important details from your letter, it seems very likely that your friend’s feelings about you are of the same flavor they used to be — deeper, surely, after so many years of closeness, but not of a different variety. This isn’t the answer you want most, but I am worried that’s clouding your ability to see that it’s still a really wonderful answer. Having a best friend rules! Having best friends who trust you with the vulnerable corners of their selves, as you two clearly do with each other, is one of the most amazing things about being alive.

At this point in your relationship, I think you have to decide if you can let that amazing answer be enough, really enough. You have to evaluate if you can experience the friendship not as a consolation prize or a waystation for your ultimate destiny of romantic partnership with them but as a gift that is exactly what you want. I’m not saying you have to force yourself to let go of the crush, which may not even be possible. Sometimes these things just linger — my longest running unresolved crush on a dear friend has been going on for (checks calendar) 9 years. But it is background noise, a little special effect sparkle alongside the main event, which is an amazing friendship.

Can you imagine yourself getting there? I think you have to answer that for yourself before you even consider sharing how you’re feeling with your friend. Which brings us to your actual questions.

As far as how to deal with jealousy, protectiveness, and resentment if their new crush progresses to a relationship, the only way is to not let those feelings get any oxygen to begin with. That means adding “that should have been me” to the stack of ideas removed from the miasma of this situation and stored as far away as you can tolerate. It will hurt to separate yourself from that idea, and I’m sorry, but it’s not real, and it’s detrimental to you and this friendship. Work on peeling apart your ideas about yourself from your bestie’s new crush, because it’s highly likely that from their perspective, the two are completely unrelated.

My hope for you is that you can accept that you and your bestie aren’t going to be together romantically, AND, this has absolutely no bearing on your worth as a person or how hot you are or if your kind of body is desirable. Note, I’m not saying to just get over it or anything impossible like that. And if you find that you can’t, or that in the meantime it’s too painful, have an honest conversation with your friend about what you’re feeling and what kind of space you need from the friendship or from hearing about their dating life so that you can do your own work to come to terms with the friendship as it is. I have a lot of hope for you, LW, and for this friendship, and I’m wishing you every good thing.

You can chime in with your advice in the comments and submit your own questions any time.

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Adrian is a writer, a Texan and a Presbyterian pastor. They write about bisexuality, gender, religion, politics, music and a whole lot of feelings at Autostraddle and wherever fine words are sold. They have a dog named after Alison Bechdel. Follow Adrian on Twitter @adrianwhitetx.

Adrian has written 153 articles for us.


  1. this is a good, thoughtful, caring answer <3 LW best of luck to you in integrating this new development, and in finding the right person for romantic partnership- even though it doesn't sound like that is this friend, it sounds like you have an amazing friendship and that is a very special thing indeed.

  2. Adrian, all of this was so lovely and perfectly put! “Attraction is a cocktail, not a shot” is a quote I’m gonna file away in the Smart Stuff AS has taught me file for sure!!

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