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,

I recently started casually online dating after leaving an abusive marriage, and it’s been going great! There have been lots of nice guys, and we have had some sexy fun. That said, I’ve run into a weird situation that I’m almost certainly overthinking but am baffled by.

I used to work in adult retail in my early 20s and am a very empathetic and sex positive person, all of which is information I share either before meeting or on the first date. I went on a first date last night with a great, interesting, funny guy that I got along very well with, who told me after dinner that he has a medical condition that causes incredibly painful erection

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