This was my impression as well … the weirdest part to me is that this was presented as a “secret” he could potentially keep from her. I’m in the same general age cohort, and man, college feels like it happened during the Dark Ages for me. I don’t even remember a lot of stuff that I got up to in college … and that’s not even a reference to partying too much, either. It was so long ago, I didn’t even have email in college! Who knows what I was up to? If anything, that would be a funny story from college … not a big secret to harbor or reveal.
If I was the girlfriend, I guess I would be wondering why it’s still such a big deal.
Did he bring up it up out of the clear blue, or was it one of those “Did you ever … ?” curiosity conversations that people have when they’re dating?
Just one without experience.