What do you regret?

Following up from a post in a separate thread (http://boards.straightdope.com/sdmb/showthread.php?t=628737), I thought I’d like to know what things people regret the most…

For my part, there are two things:

The first occasion occurred when I was in college (in 1990). I had a huge crush on a girl (who I will call Sarah, for the sake of this post) who was, if truth be told, WAY out of my league - she hung out with all the jocks and I was…well…not a jock. She was really cute and there were lots of guys who had the hots for her. However, she was best friends with a girl who was dating a friend of mine, so I saw an ‘in’…

Somehow, my friend’s girlfriend managed to convince Sarah to join the three of us for dinner together to a restaurant (which was a big deal, since we were poor students). After dinner, we all went back to my place (my room, since I was living in a student residence hall) and after a period of talking and drinking, my friend and his girlfriend made their excuses and left, leaving me and Sarah alone.

We sat together and chatted (her on my bed and me on a chair), and at a certain point, I managed to sit next to her on the bed.

And there I sat… and sat… and sat. I was too afraid to make a pass at her (I was thinking “What if I move in for a kiss and she says “Uh, no, I’m not into you” and I’m horribly embarrassed”) and so we chatted, 6 inches from one another for 40 minutes. Eventually she figured out that I wasn’t going to make a move and she left.

The next day, my friend’s girlfriend called me and said that Sarah had actually thought I was cute, but that by not making a move, she’d figured that either I just wasn’t that into her or that I was a sad, sad man with no guts. Either way, I’d blown my chance. I felt like saying the obvious (“Why the fuck didn’t you tell me before we went out that she liked me!”) but I refrained. I did see Sarah again quite a bit, but she never showed any interest, and obviously, I really had blown my chance.

So 20 years on (happily married for 9 of them), I still look back and regret not making that move. Randomly, I recently saw some photos on Facebook form a mutual friend of a group of us (including Sarah) and it all came flooding back…

It’s weird, because this was someone who I knew for a few short years during college, when I was young, and yet it had a profound effect on me ever since. After that, I’d like to say that I was more ‘forward’ than before (not aggressively so, just more along the lines of “It’s better to regret doing something than not doing something”), but this really did change me. But yet I regret it. Ah, Sarah…

So, anyone else want to share, or is it just me? If anyone else throws in their story, I’ll add my second regret story - less teenage sob story, more interesting.

I regret so much of my life that if it were a painting, half of it would be smeared.
BTW the sexiest thing in the world is confidence.

Some of my biggest regrets are too painful for me to talk about, but I’ve definitely had my share of relationship regrets. On the other hand though, I think that a lot of times these relationship things work out for the best.
In your story, I don’t think Sarah sounds like a very nice person. She sounds like one of those girls who would get upset that a guy can’t read her mind. Instead of jumping to a negative conclusion, she could have looked at it as you being a gentleman rather than gutless. And, of course, there was nothing stopping her from making the first move. :slight_smile:
I bet your wife is nicer. :slight_smile:

So what was the second thing?

If cigarettes are regrets, I’d smoke em too.
(Don’t ask me what that means…)

I’ve had relationship regrets also, but even some of those decisions were the result of something wonderful. Although I spent a number of years unhappy and disappointed, I have two great kids. Regrets can teach you what not to repeat the next time around. Life is delicate and short and I am convinced more every day that when you come across someone with whom you are compatible with you must try your best to pursue what you want. Not that any relationship is perfect…if you are seeking perfection you will never find it. I’ve had professional regrets also, but there too, I am making thoughtful and better decisions this time around and working hard towards goals that will ultimately allow me to be happier and financially secure. For the most part, I try not to dwell on every big and little regret. If I did, I wouldn’t have the energy and power to move forward.

My first regret would be continuing to pursue a degree in a field that I KNEW I hated. But by that point I had dropped out of so many programs that I was determined to finish SOMETHING and stuck it out. Now I have a degree that’s pretty worthless (haven’t worked in the field for like 5 years) and $20k in student loans I can’t afford to pay. If I had just given up that one last time I wouldn’t be in this financial mess :\

And my second (and bigger) regret is deciding to get married when everyone told me not to. When my own gut told me not to but I did it anyway because I thought it was the ‘right’ thing to do for my daughter. Marriage didn’t even last six months and now I’m in a worse situation than before I tied the knot.

But the problem is that in the real world there’s no obvious line between being confident and being creepy. Usually the only difference between the two is whether or not the other person finds you attractive.

There are a few could-have-been-lovers I regret not having. But they might rank behind shouldn’t-have-been-lovers on my list of regrets. :dubious: Neither category will appear in my Top Ten list.

Me too. And I regret that my worst regrets are too painful and horrid for me to even hint at here.

I regret not knowing this 45 years ago.

On a happier note, I luckily avoided death and incarceration, and accumulated enough savings to retire modestly. Mr. and Mrs. Septimus are comfortable with two wonderful children. We are the envy of our friends and neighbors … (although this is partly due to the severe self-made problems of our friends and neighbors :smack: ).

You, America. I regret you.

Cigarettes are a good one – it took a good bit of effort to stop once they became a habit. Beyond that, I don’t know – everything silly or short-sighted served as lessons for me. I would regret losing all my possessions (books, and papers) if it ever came to that, but one thing I don’t regret is having kept those relations who could keep a few things for me in storage if I wound up in the pokey or homeless.

Regrets. I’ve had a few. But then again…

Hmmm. That’s true. Maybe real confidence comes from a place where you already feel that there is some connection? I dunno. To me:
Ashton Kutchner=accessible.
Barny from How I Met Your Mother=smarmy.
For whatever that’s worth.

My biggest regret is having started drinking. While I never got in serious legal trouble (pulled over for DUI a couple of times, but never arrested), and never lost a job due to drinking, I became an alcoholic, and came very close to losing my family.

But on January 30, 2012, I’ll have been sober 12 years.

Almost all of them have female names, and the majority are labelled ‘didn’t while I had the chance’ (or usually ‘didn’t know I had the chance’), and the minority ‘damn, that was a mistake’.

The other one is following my then-girlfriend halfway round the world. I shoulda stayed put, because I was very happy with life there, but then at the time I couldn’t imagine life without her. I soon found out what that was like. :frowning:

Mine is the exact opposite. I should’ve gone, but didn’t.

For a partner?

This post.

Yes. We met when I was doing a placement at her university. We hit it off pretty fast, and spent the summer together - the best summer of my life, really. I went home to graduate, but had a decent shot at coming back for grad school. I chickened out, we did long-distance for a while (not much fun when you’re both students and can’t really afford intercontinental travel) and I broke up with her some time later. If I could change one thing in my life, that would be it.

I should have moved to Charleston a decade earlier.

I regret not studying abroad in Chile my sophomore year of college. I was severely depressed and I let that be an excuse not to go.

I regret betraying the secret of a friend who abandoned me, out of apathy and maybe spite.