How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous! Dear How to Do It, My boyfriend and I are both transmasculine and have been together for a ...

DEAR MISS MANNERS: My boyfriend wants to take me on a date that involves dressing to the nines. He would like to see me in a super fluffy ballgown, which is a request that I am willing to oblige if I ...

Like seemingly everyone else on the Internet this week (at least, my corner of the Internet), I have been fully wrapped up in the latest iteration of drama between celebrity exes Olivia Wilde and ...

DEAR HARRIETTE: My boyfriend is shorter than me. We always knew this and laughed about it at first. Recently, we have been going to dress-up events, and I have worn heels. Nothing too high, like 1½ ...