It’s a risk, I suppose, in the sense that asking out anyone is a risk, but it’s not such an inherently risky proposition that you shouldn’t do it. Asking a friend to go out with you is not hurtful. You are allowed to come out as bisexual if you’re only attracted to one of your friends named Greg and haven’t first run a hypothetical attraction test on all the other men in the world. You are allowed to come out as bisexual in your late 20s. He worried that it was his “fault” and that I wouldn’t want to be friends anymore. But he concluded I was angry with him, texted me an upset-sounding apology. I also texted him the same information, just in case. I had to leave early the next morning for a work emergency, so I left him a note (along with a glass of water and some aspirin) explaining why I had to leave. I initiated it, and he asked several times if I was OK with what we were doing. I was at his place recently, comforting him over a breakup we got drunk and slept together. Possibly bisexual: I have always identified as a straight guy, but I am recently panicked and confused by feelings for my best friend (a gay man), “Greg.” We’ve known each other since college and have always been close.

Here’s an edited transcript of this week’s chat.ĭaniel Mallory Ortberg: Hi, everyone! Hope you all enjoyed the break-now it’s back to your regularly scheduled Dear Prudence. Daniel Mallory Ortberg is online weekly to chat live with readers.