My dad has a friend with three sons, who I will refer to as oldest, middle and youngest. I’ve seen them on occasion growing up, but not more than once or twice a year.
About a year ago I (25f) ran into youngest (22m) at a club and we chatted and drank (too much) and he ended up spending the night with me. We have absolutely nothing in common and didn’t really keep talking afterwards. I asked him if he was planning on telling his family anything about it (because my parents would not be happy if it got back to them) and he said he was just going to tell his brother, the middle. Cool.
Last week oldest got married. Youngest now has a girlfriend and both of our sets of parents are trying to set me up with the middle (24m). We ended up hanging out for a lot of the night and now we’re texting and he’s being pretty flirty.
We have a lot in common and if I hadn’t been an idiot that night a year ago, I think we might really have something here. Personally, it doesn’t bother me, but I can’t imagine it not being a deal-breaker for him.
So now I’m wondering whether youngest ever actually told him. Is there any chance he knows and actually doesn’t care? At what point, if any, do I need to bring it up? And how? I am confused.