I should also make it clear that I’m all for regretting genuinely bad choices. If, say, marrying someone (or running off with someone else, or whatever) was clearly a bad idea at the time, and you went ahead anyway despite the warning signs, then feel free to beat yourselves up for any disastrous consequences.
Gosh, I have a lot of regrets, and I suspect they’ll continue to pile up. One of the overall themes is that I should have tried harder, pushed more, not taken No for an answer. Many things would have turned out better if I’d just kept trying and not given up so easily.
Even knowing this, I still tend to just accept things that don’t necessarily HAVE to be accepted.
I should have kept my first job, where I was the first employee. I would have ended up owning a multi-million dollar business with a hundred employees, and I would have sold it about 10 years ago for cash.
Rats.
Not working hard enough at it to become fluently bilingual.
You don’t know her.
In the end, I guess I didn’t either.
Not living the solitary life I knew was right for me.
Not handling the $8000 well I received from the 401k I cashed out from the company that laid me off
My stupid a$$ deposited all the money in my checking account and took rent out of it instead of opening up a savings account and putting it up
Biggest regret I ever made in my life
Jman, I’m sorry you had that experience. We’re stupid when we’re ten. But I know the regrets are sort of like we did those stupid things as adults, and it’s not fair or pleasant. I definitely could have done exactly the same. I sympathize and wish the memory could be erased for you.
My regret is not helping my grandmother when she was struggling to take care of her house and I was in my late teens. Which, sadly, is a pretty adult regret.
What do you mean - would you have been happier if you hadn’t gotten married and/or had children? Something else?
I wish I had taken some art classes in high school. I would have gotten a scholarship to study architecture at Yale, but they wanted to know why I hadn’t taken any art classes. “I didn’t need them” wasn’t an acceptable reason.
That would about sum up me too. 'Nuff said for now.
I regret not staying in Beirut after 2006. If I had, I could have spent the last 8 years of my life happy, instead of unhappy. And the next x years, as well. I had a good life there.
I don’t have deep regrets. I’m incredibly lucky in the life I had led, although bad things have happened to me and those around me, things have usually worked out okay. I’m also a naturally optimistic person so don’t tend to dwell on mistakes I’ve made.
The closest I can get to a regret is an annoyance that I followed the ‘healthy eating guidelines’ for so long.
Not ‘cutting loose’ more when I was a teen/young adult. I was always so scared and just didn’t get up to many of the hijinks that make good stories later. I wish I had just relaxed a little more.
Regrets I’ve had a few
But then again too few to mention
I regret not learning to swim until I was 48, missed out on a lot of activities due to feat of the water. :mad:
I also regret not pursing many young girls interest in me due to attractiveness alone. As I get older I realize that they were not really unattractive and that I likely missed out on getting to know some good people and that most of the attractive women I did have relationships with were superficial people. 
And lastly I wish I had kept in better contact with distant relatives before they got too old or passed away.
My deepest regret: giving up any hope of ever finding love at age 30. In my early teens I considered it a foregone conclusion that I’d marry and be be a father; in puberty and later I somehow learned that I was utterly unattractive to women.
Later at age 47 I cleaned up my mental act and some time later got utterly surprised one evening. We are almost four years together and it still gets better.
This reminds me of a minor regret that I think about. Picture it, I’m in college working at a local grocery store. A friend from school comes in to buy flowers for a girl he is about to meet up with. It’s just about closing time so he waits for my shift to end and gives me a ride to where I was going to hang out. I’m about to get out of the car when he kisses me! (at this point, I had only kissed one other person) Now, a number of thoughts occur to me: didn’t you just buy flowers for some other girl? and I am seeing someone so I personally shouldn’t kiss you back, even though that person wasn’t particularly faithful to me… So I kind of vaguely shake my head at him and get out of the car. We remained friends and all, but it would have been fun to at least smooch for a while and he was really sweet and sooo cute.
I still have a crush on him so I googled him and of course, he died in 2009. And now you know the rest of the story. 
I too wish I could erase this for you, and a bunch of times I have put my foot in my mouth! It reminds me of Terms of Endearment (bear with me here!) when Debra Winger tells her older son who is acting like a poopyhead – you’re going to look back and feel bad about how you acted toward me and I’m telling you, don’t. I know you don’t mean it.
This is a good thread. Not because I’m going to tell you what my deepest regret is, but because I tried to, and then I found that the couple of things I was going to write about weren’t as bad as I thought.
So, I spent time thinking about a couple of difficult things, and came out better on the other end.
Thanks!