This list seems to fit the mood, so here we go.
I should have been a caddy at the country club instead of a researcher at the library
I should have stayed in Washington DC
I should never have kissed Cynthia
I should have looked harder for a job in my field instead of settling for where I ended up.
I should have kissed T.
I should have started having sex way earlier
I should NOT have lost my temper that day in the Raquetball court.
California was a mistake.
The hot tub with the architect was not a good idea.
The hot tub with the fashion designer would have been a wonderful idea
Buying lingerie for C was funny, but not very smart, even if I did get her sizes just right.
I should not have quit skydiving.
I should have gone down on K when I had the chance.
My career has been completely by accident. I should have taken charge a long time ago.
I should NOT have deleted all my blog posts and the pictures of my beautiful friends.
I should have told CTR to fuck off months before I did.
Judging people for their past mistakes when I had plenty of my own in my near future was cruel.
K loved me, I should have loved her back.
I should have learned Spanish.
Maybe I should have stayed in Italy and given it a shot.
Who am I kidding? She didn't want me to stay.
Apparently, I should have taken out more student loans...
