the cut on tuesdays

How to Tell Your Best Friend You’re Trans

Photo: Photo Illustration by Stevie Remsberg; Photo: Getty

The Cut on Tuesdays

A weekly podcast from the Cut and Gimlet Media, with host Molly Fischer.

This week, we’re talking to Daniel Mallory Ortberg and Nicole Cliffe — co-founders of the much-mourned website The Toast — about how they became friends, and about what it’s like to make and remake a friendship when your friend is going through enormous changes.

For Daniel and Nicole, one of those changes came when Daniel started to think about transitioning. They’re able to talk through all this stuff now, but along the way, there were many dropped hints that did not get picked up.

Nicole: I remember Danny showed me this Instagram page, which I immediately added because it’s very beautiful. It’s like, it’s FTM transition. So, just before and after pics, essentially. Danny would be like, you know, “Oh, my gosh. He looks so amazing. How cool is this?” I was just in my head, just like, “Yeah, Danny definitely thinks that like trans dudes are supercute. That’s great.”

Molly: Just filing that away, yeah.

Nicole: Just filing that away. And I think it was two years before we had any conversation, any conversation whatsoever that there might have been more to that.

Danny: And of course, in my mind, I’m like, “Oh, yeah. Nicole gets it. We’re on the same page here.”

Nicole: No, Nicole did not get it. I don’t pick up on hints. I think that probably for months, Danny had been attempting to get me to figure out on my own. I’m sure that what Danny wanted very much was for me to ask, and I failed to do that, because I am a dumbass who does not put things together. Hints or otherwise. So, what Danny eventually did, I think it was a text message that was just, “I’m sure you’ve noticed that I’ve been thinking a lot about gender recently, and I don’t know what any of that means, but if you wanted to periodically call me a beautiful boy, that would be good for me.”

Danny: That is so me. Oh my God. Like, a lot of careful couching and then a divaish request to be called beautiful. That is extremely on-brand, and I believe it completely.

Nicole: And I was like, “Oh, oh, of course.” And then like lay on my bed for an hour being like, “Oh, okay. Okay. This is happening. This is something.” I felt bad later that I had been like a poor friend in that there are things I should have noticed. I remember realizing that like Danny had been talking about this with other people who weren’t me, and I felt such jealousy so briefly in that moment.

Danny: I think that was kind of one of the first times that we kind of bumped up against, “How do we talk about things where we don’t believe right away we’re going to be like, Yes, you and me. Friendship magic, same as before, we intuitively and immediately understand one another?” How do we relate to each other when we have to talk stuff out?

To hear how Danny and Nicole got better at talking it all out, click above to listen — and subscribe wherever you get your podcasts.

How to Tell Your Best Friend You’re Trans