I had a date with this girl, it was good going until she started talking about her high school and things like regret or whatever - completely broke frame. I had a terrible high school experience with very little friends. The few friends I had, we'd just hangout at school and not really do anything. Now this girl hangs out with people all the time, and does stuff with them. I felt like a fucking loser telling her that I didn't do much in high school or in my first two years of college (had a super beta LTR with this starfish girl and we barely did anything fun).

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I'm sure this is something I'll encounter in the future when dealing with girls who are of high social value, how might I not break frame in this case?