Not a dating scenario, but I once had a coworker ask me how long I had a stutter and she mentioned one of her friends had one. The way she said it so casually like it wasn't a big deal made me feel at ease and I was open to talking about it with her. Oddly enough, no one had ever asked me that before, probably because they didn't want to sound offensive, which I understand. For me personally, I thought it was cool how she asked me about it.