Dear Prudence

Should I Tell My Fiancée I’m Trans?

Prudie’s column for March 16.

Diamond engagement ring intersecting with the Transgender symbol.
Photo illustration by Slate. Photo by mevans/Getty Images.

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Dear Prudence,

I came out as trans to my parents when I was a teenager. They weren’t supportive, and I was sent to see a psychologist I didn’t feel comfortable talking to. I felt so guilty about the high copays that I claimed it was “just a phase” and even managed to sort of convince myself. I’m now in my early 30s, have a great career, and am engaged to a wonderful woman, but I still experience the desire to transition. My fiancée knows I saw a therapist when I was a teenager, but she doesn’t know the details, and it’s weighing on me. In the last three years I’ve been having recurring dreams where I get to be a woman, and when I wake up, I feel so depressed I can’t even get out of bed. I just want to fall back asleep and dream again. My question is twofold: Do I owe my fiancée an explanation? Do I call off the wedding? I don’t even know where to go from here. Part of me wants to keep things as they are, looking forward to these dreams as they come up and thinking about what could have been. The other part of me wants to scream who I truly am to the world and deal with it, even if that means losing everything.

—Can I Come Out Again

Instead of asking whether you owe your fiancée an explanation or whether you should call off the wedding—which frames your thoughts and feelings about your gender as a shameful secret that you’ll have to atone for—ask yourself whether you would want your fiancée to be able to come to you if your situations were reversed. Even if you were surprised or ultimately found that your orientations weren’t compatible in the long run, I don’t think you’d be angry—you’d be grateful to know what was causing your partner deep distress and ready to offer compassion and support. You’ve already tried to downplay your desire to transition, to minimize your longings, to dismiss your identity as “just a phase” that’s not worth burdening other people with, to keep it to yourself. And while you’ve been able to build a lovely life, the anguish of feeling totally alone, like this is the one part of yourself you can never share with anyone else, has you wishing you were asleep 24 hours a day. Implicit in your letter is the fear that it’s too late—that because you didn’t transition when you were a vulnerable teenager without meaningful support you can’t now, because you’re in your 30s and have a good job and a partner and are too invested to consider transition now.

So no, I don’t think you should talk to your fiancée because you’ve violated an implicit contract never to consider transition. You should talk to her because repressing your thoughts and feelings about the possibility of transition is absolutely crushing you, and you shouldn’t spend the next 10 or 20 or 30 years psyching yourself up to make it through the day for other people and waiting until you can really live in your dreams. If your city has any support groups for trans people and people questioning their gender identity, I’d recommend stopping by for a meeting and getting a sense of how many different paths to transition there are and how many of us come to it in our 30s and 40s and 50s and later. The question of where to go from here is totally up to you. You don’t have to do anything you don’t want to do or don’t feel ready for. But talking to your partner, a therapist you trust, a friend or two, and other people who are contemplating transitioning is a good start.

Dear Prudence,

I recently broke up with my girlfriend of about a year. We’re both in our mid-20s. I broke up with her because I recently just bought a house, and as I enter this new phase in my life, I was not sure that I wanted a serious relationship, and I did not want to lead her on when I was unsure of what I wanted. She completely understood, and it was amicable. A month out from the breakup I find myself missing her. Some days it’s not that much, and some days it is a lot. My problem is that I am having a hard time trying to figure out if I miss her specifically or if I just miss having someone in my life in that capacity. Part of me thinks that if I wanted to be with her, I would have no doubts. I haven’t talked to her since our breakup, so I’m not even sure if she would want to get back together. Is there a way to figure out if I miss her or just miss having a girlfriend? Is this just post-breakup blues and I’ll move past this sooner or later?

—Reunite or Not

A month out from the breakup isn’t really enough time to have a strong sense of whether you miss that particular girlfriend or simply having a girlfriend. Give yourself another couple of months to adjust before trying to draw any bigger conclusions. I think it’s worth noting that you don’t describe either being with your ex or not being with her in very strong terms: You weren’t sure of your commitment, you broke up, she understood, sometimes you miss her, and you’re not sure what she might be thinking or feeling now. It sounds like you were less conflicted about buying the house than you’ve been about this relationship. That’s fine, and kind of what your 20s are for. It sounds like you’re worried that you’ve made a mistake if you sometimes miss your ex, but just because you occasionally wish you could call her or see her doesn’t mean you made the wrong choice. You don’t have to be completely indifferent for a breakup to be a good idea. You’d spent a year together and experienced a nonromantic milestone that helped you realize you didn’t feel especially strongly about your relationship, so you were honest with her about what you could and couldn’t offer her, and the two of you parted ways. Since you don’t have any new information to offer her other than you still like her (which you both already knew), I think you should keep up the no contact for a while longer. Spend some time being single and figuring out what you do want next, rather than just rushing back to your ex because you’re not sure what to do with your periodic bouts of loneliness.

Catch up on this week’s Prudie.