Sometimes when I am feeling a little guilty about my adolescence I think about the dozen or so otherwise date-free girls who I escorted to proms, weddings, etc. at the behest of my older sister. One of the best pieces of advice I ever got was to make that date feel like I was not just a forced fixup. My sister was a smart gal.
I think you’re a smart guy, who had fun with a lot of grateful girls who may not have been prom queens but were probably great people nonetheless. And I am sure those social qualities have helped you in your professional life as well.