Dreher misses his never-happened twenty-something sojourn in Europe. But he wanted a wife and kids and thought he'd be on the shelf if he waited too long.
The regret I have about never having lived in Europe is very, very mild -- but that's because I have what I most wanted in life (a family). If I had reached middle age without marrying, and was locked into a job I couldn't now afford to leave because I needed the health care, or for whatever middle-aged reason, the regret would be fairly unbearable for me.
I can't see the iron-clad logic of that myself. But he asks an eternal question: what does one regret? Most of the candidates, as Rod notes, are two-sided. I regret deeply getting HIV. I still don't know how it happened, but it did, which means I wasn't being careful enough in my twenties, as many young men can testify to as well. And yet, looking back, how would my life have been without facing mortality so young? I tried an answer here. Not so simple.
Do I regret leaving Britain and what would probably have been a political career - now part of a truly exciting experiment in liberal Tory governance? I think at some point you understand that this is the life you have, a consequence of countless tiny decisions that didn't even seem like decisions at the time. I loved America from the get-go but the decision to immigrate was never clear, always incremental, beset by fate and chances and love and illness.
And this is life. It is an adventure, not a plan. Regrets are the flip-side of freedom. I'd rather have both than neither.