re: Does anyone else regret not playing high school sports ?

I played HS football. The only reason to play sports is because you enjoy it, not because you think it will somehow make your life better. It doesn't work that way. No regrets, but it didn't make me a 'cool guy,' and nobody gives a shite about any of that stuff after you graduate anyway.

If you want to meet girls, sports are the wrong place, because they ain't there except maybe once a week, and you're on the field while they're in the stands. Do something where you'll actually spend time with them. Join the band, or better yet, the theatre department.