I used to use this as an icebreaker, until I got a very uncomfortable response from a female colleague. Turns out that whilst men’s “worst dates” are usually weird or awkward, and tend to make for good light entertainment and a little window into their lives, women’s are way more likely to be sexual assault related… Made me wonder how many answers I had heard in the past were glossing over some trauma that didn’t need to be brought up in a social setting.

I now usually rely on the way more positive “what’s the next thing you’re looking forward to?”.