One time I was on a date with a woman who was talking about her ex for a while. After she was done talking she mentioned something about past relationships (in general) and I said "I've never been in a relationship, if it wasn't obvious." And her response was "Yeah, it was obvious," and then she proceeded to drill right into the fact that I'm really insecure and don't understand social dating norms that well. It probably would have hurt my feelings a lot if it wasn't all so damn true. After that I was sure I ruined my chances with getting anywhere with her but then like......she seemed to still show interest in me and even said something implying she wanted to hook up and I was like wtf. I ended up not going anywhere with her on that date because that convo (where she called out all of my insecurities) made part of me think that she didn't want to go anywhere no matter what. We tried to schedule a second date but our schedules didn't work out (admittedly this was mostly my fault, she was willing to meet the next week so maybe she did want to, idk).
