How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here . It’s anonymous!
Dear How to Do It,
I recently finalized a divorce, after having been married to my wife for 10 years, and am now back on the dating scene. I’m mostly looking to have casual sex with someone I can connect with more than once. The problem is I went on a few dates with this one woman, and after a night of drinking, we had sex. It was great, but then I did something that really embarrassed me.
I inexplicably started crying. It was my first time having sex with anyone other than my wife and I guess it just hit me at that moment. She was really nice about it, and I hope we can patch things up. But it’s so awkward and I really don’t want that to happen again. How do I