I'm a lesbian and my now-boyfriend recently came out and socially transitioned, and I don't feel comfortable dating him anymore.

G
asks:
I'm a lesbian and I've had a girlfriend since last year. Things were going great, but now he's my boyfriend, L. I don't have an issue with L being trans at all, but I don't feel anything for him anymore and I don't feel comfortable dating him if he's not a woman (or at least woman-aligned). I don't want to hurt his feelings since he's having trouble being accepted by his parents and people at school, and I don't want us to stop being friends, but I really want to break up with him. To make things worse, I lied earlier in the year when he asked about this same problem, and I said I didn't have a problem with dating him now that he's out. How do I break up with him in a way that won't hurt him or our friendship?
Mo Ranyart replies:

First off, in case it helps to hear this: it's all right to want to break up with your boyfriend. You're allowed to end a relationship for any reason, and "I only want to date women, and my partner is now very clearly not a woman" is a perfectly valid one. Sometimes, a person's gender transition means their relationship no longer fits the framework of their partner's sexual orientation, and as a result, that relationship must end or evolve into something that's more platonic than romantic or sexual. While it can certainly be a sad part of an otherwise happy and affirming process, it doesn't mean either of you are at fault or are doing or feeling something wrong.

I want to say that up front because, after reading your question, I get the sense that you're feeling guilty about wanting to break up with L. Breakups suck, for the most part; it's understandable that you'd feel upset thinking about doing something that will hurt a person you care about. At the same time, though, it isn't wrong to end a relationship you no longer want to be in; in fact, I'd say it's going to be the kindest choice you can make. Staying in a relationship when you know you'd rather break up won't avoid problems; it might postpone the immediate pain of a breakup, but it's likely to make that breakup feel worse for both of you when it does eventually happen.

Plus, since you already know you aren't interested in continuing the relationship, the odds are good that L will figure out that there's a problem before long, if he doesn't suspect it already. I don't want you to be in a situation where you feel forced to fake affection you don't feel; that wouldn't be kind or fair to either of you. In the long run, I imagine you'll be able to support L better as a friend and ally, rather than a reluctant romantic partner.

Sadly, I don't have any secret breakup techniques that can guarantee a perfectly smooth, pain-free breakup that doesn't impact your friendship in any way. It's likely that he will be hurt by it, and there isn't a way to have that conversation with him that can keep that from happening. What is possible, though, is for you to act with a lot of kindness and compassion, give him space to feel whatever feelings he has about the breakup, and hopefully continue a strong friendship when he feels able to do so.

What I think is best to focus on here is finding a way to end your dating relationship that's clear and compassionate; you can't shield L from hurt feelings, but you can do your best to break up with him as kindly as possible, while offering whatever ongoing support you're comfortable with. It sounds like he doesn't have a lot of support right now, so if there are ways you'd still like to be there for him when you aren't dating, I encourage you to be clear about them when you're talking about how you want to end or change your relationship. Affirming your support for his transition and his gender somewhere in this conversation will be a kindness to him, so he can be very clear that you still support that part of his life.

A sample script to build on might look something like: "I care about you a lot, and I've enjoyed so much about our relationship, but I've come to understand that I need to date a woman to be happy in a relationship. Continuing our friendship is important to me, and I want to keep supporting and affirming you, but I need to end our dating relationship."

I hope you'll go easy on yourself when you think about the "lie" you told L when you said his transition wouldn't be a problem for your relationship. I can't know what was in your heart when you said that, of course, but I can't imagine it was something you said maliciously. Maybe you wanted to spare his feelings during what was likely a stressful time, or it felt like too much to break up when you were aware that other people in his life weren't being very supportive, or you were determined to find a way to be happy in a relationship with a guy. Whatever the reason, I doubt it was in any way an intentional attempt to mislead him; I encourage you to extend some compassion to yourself and call this something other than a lie, if you can.

If he asks directly why you said his transition wouldn't be a problem for the relationship at an earlier time, you don't have to share—or know—your exact reasons; it's all right to say that you truly hoped it wouldn't be an issue, and that you wanted to give it a try because you care about him so much.

As I said before, there isn't a way to break up with L that will guarantee he won't have hurt feelings about it, as much as I wish there was. He may need to take some time and space away from you for a while, but hopefully, when he's ready, he will reach out to you again and you can work on building on the friendship you still want to share. It's common for people to withdraw a bit after a breakup, but with a solid friendship in place it's also common for ex-partners to be able to come together as friends after some time apart.

A few years ago, I answered another question with some general advice about how to break up with a partner you want to remain friends with; I think the entire thing might be helpful to read, but I want to leave you with my closing thought from that column, which I think applies here as well:

Lastly, it's important to remember that while breakups are often tough for the person being broken up with, they're not always a breeze for the person doing the breaking up, either. Particularly if you still care about the other person - and it sounds like you do - it can be difficult to see them unhappy, and adjusting to being single again can take a while, even when you know breaking up is the right thing to do. Give yourself some time to feel whatever you might feel: it could be relief, happiness, sadness, all of the above or something else entirely, but whatever it is, it's okay. Change, even when it's ultimately positive, takes some getting used to. If you don't already have some self-care strategies that you know work for you, this is a really good time to develop some. Journaling, connecting with friends, or taking on new projects or activities could all be great ways to take care of yourself right now.

I encourage you to be just as gentle with yourself, in this entire process, as you are with him. I'm hoping for the best for you both.