Middle age surprises. Crack-addicted friends with bad chips on their shoulders in 1992 have since made peace with themselves, started families, replaced missing teeth, and become altogether wonderful people. Great womanizers who cavalierly juggled supermodels in their twenties now find themselves alone, with suspicious suntans and too many Chrome Hearts rings on their fingers.

In my early-thirties, terminally single, I found it hard to get through dinners with happily...