This is a very interesting question to ponder. By trying to imagine myself in twenty years and saying what I wish I had done, I am admitting that I have failed to do something. But what will be my failures in twenty years? My regrets might be radically different than anything I have ever imagined. Will I even live another twenty years from now? A question like this can really make one think.

I guess one regret that might occur if I don't find a consistent lover sometime between my current age of 27 and 47 will be not pursuing something further with a girl named Maryanne that really liked me when I was 22. We lost our virginities to one another and this girl really wanted to be with me but I didn't see a connection after a short while, so I quickly ended it. Sometimes I think maybe I should given her more time. Maybe I would have grown to really like her. In these past five years, I have went on dates with over a dozen or so girls and have had some hookups but nothing consistent that might have led to a relationship. If I don't find something consistent by the time I'm 47, then maybe Maryanne will be the one regret that I wish I did earlier in my life because I always got the feeling that she was willing to do anything for me. Perhaps I would have been really happy with her.