I wish that I didn’t win both games of chess with my acquaintance in university and instead kissed her.

I sometimes wish I had married the 2nd guy I was engaged to. It wouldn’t have lasted, but damn, we would have had some fun!

I had a girlfriend in high school who wanted to have sex, and I felt it was too early in our relationship, which I wasn’t very serious about.
She was crushed, and ended up bedding a friend of mine, who I know didn’t care for her.

There’s a list of certain women who….well you can all see where this is going.

I can think of a number of times when I was too cautious and should have taken a chance. If I’d made a few more of the smaller mistakes just for practice, maybe I could have avoided making one or two really big ones.

I think I made the best decisions I could at the time.

I kind of wish I’d have had a baby with my ex.

I wish I would have broken more rules as a teenager. I wish I had been more promiscuous and lived how I felt inside and not been so reserved and afraid. That’s what being a teen is all about right? And it seems like everyone but me got into mild trouble as a teen except me. I don’t have good stories or life experience because I always just did the right thing and stayed obedient.

@BackinBlack It’s not all it’s cracked up to be, being bad. I only tried it a few years and saw things I wish I hadn’t. Learned a lot of bad things from bad people. I promise, it wasn’t exciting, it was flat out scary.

I agree with @KNOWITALL.