What Is Your Biggest Regret In Life?

There are things I wish had gone differently, and decisions that look stupid in retrospect, but I’m pretty content where I am, so I can’t say any of the regrets are overwhelming.



I coulda had a V-8.


I regret not going to college right after high school and not figuring out what I wanted to do with my life at that time, instead of waiting til the ripe old age of 34 and having to juggle school, work and other grown-up responsibilities.

Also, there was a guy I dated several years ago whom I was crazy about, but I stupidly, and all but deliberately, drove away. A few months later I met my current SO, and I couldn’t have gotten a better one if I had one made to order by Og. But still, I sometimes wonder about the one who got away; I hurt him, and my heart still aches when I think about him.

Probably my biggest deliberate mistake was choosing a very large state university over a smaller, more intimate liberal arts college. I got a damn fine education, but failed to thrive socially in any way. Instead I learned to think of myself as a small fish in a very, very big pond.

Most of my life’s mistakes have not been deliberate, more a matter of failing to do things I hated, feared, or couldn’t see the point of.

Years 3 through 7 of graduate school.

My biggest regret…?

Not doing my homework. Literally. I scraped through highschool on the raw strength of my test scores, and couldn’t be bothered to do my homework. I knew the material, often far better than the teachers, so why bother? Well, I’ll tells ya why… Because colleges look at grades, not at actual knowlege, when they do their scolarship/admissions thing.

My ninth-grade English grades scuttled a National Merit Scholarship, and I couldn’t find any other scholarships, thanks to my grades. Several colleges and universities, including state schools, turned me down flatly based upon my (obvious) crappy study habits.

Second biggest regret…?

Having screwed up my chances for a scholarship, I wasted two years before joining the military. The Nav straightened my lazy ass right out. I should have gone much sooner.

I’m surprised there’s not a bunch of “oh, I have no regrets” or “everything happens for a reason” posts.

Biggest regret is that long distance relationship that lasted for two years then fell apart when we finally lived together. Big waste of time, money and emotion.
Doesn’t tear me up, over it. But do regret it.

I also regret ever getting into a long-distance relationship (well, one particular one). It ended with me being cheated on and left me with a lot of issues. I used to be one of those guys who loved having a girlfriend and sought commitment, and now it’s left me skittish about commitment and being unable to get excited about any relationship prospect. I think I’m getting over it now, but I’ve thought that before.

I suppose I also regret not learning a musical instrument or a foreign language or never developing what probably would have been a natural ability to be a good baseball pitcher (I have the perfect frame and flexibility for it, especially when I was younger, and it’s one of the few serious athletic pursuits a boy with bad asthma could handle). But it’s not like a decision on any of those things was ever in front of my face, and they’re all really as much my parents’ fault as mine.

My only two regrets are picking up smoking and dropping out of high school.

Not much point anguishing over any of it now though.

I wish I had travelled when I had time in college. True, I didn’t have money, but I could have worked around that. Because now I have money but no time, and it sucks.

I was going to say something else but **trunk ** called my attention to a biggie: I was never a traditional bully, but I held their coats on occasion and definitely joined in the pointed “HAHA” at times. Jesus, I cringe inside at my behavior now. I truly regret it and wish I had acted more bravely and more as a good guy.

I guess I also regret being so painfully shy as kid/Teen – I could have done so much more with the gifts that I had * if I could only have gotten over it a bit earlier

*meager gifts; this isn’t meant as a vain boast about any of my supposed my “gifts” such as they were, just as a regretful sadness

I waste all my time regretting, and I regret that. I shouldn’t have believed my dad when he taught me to be ashamed of everything I did wrong. Now, I spend a lot of time feeling ashamed of stuff that happened as much as 50 years ago. I know it’s stupid (and I’m ashamed of that,) but I don’t know how to get loose from it.

I regret not learning to drive earlier. I could have had a greater choice in jobs and where I lived. But, the job I had, which I took because of where I lived, brought me to my husband and the life we have now.

I regret drinking and sleeping around in college, but someone would have grabbed me up and married me and, same deal - husband and our life together wouldn’t have happened.

I regret the two times I dropped out of college. I regret veering off into education rather than staying a straight biology major as an undergrad. I regret a year spent estranged from my family over a woman. I regret both of my marriages. I regret wasting three years of my life in south Texas. I regret that I got an advanced degree in business instead of microbiology. I regret that I allowed my second wife to destroy both of us financially. I regret that I was apparently doing_or not doing_ something so egregious that a woman I truly loved left me without ever explaining why.

I should have gone forward with a 6 year Navy hitch. They were trying to push me into a field I didn’t want, and I was a hardheaded teenager who thought he knew everything. Net result is that I didn’t serve my country, and I’m ashamed of that, together with missing out on what the USN would have offered in return.

I’ve had this same thought many, many times in the past seven years. I knew law school was a mistake from the first day of orientation. Unfortunately I felt like I had no other options at that point because I’d already made the commitment. (If I could do it all again, I’d probably do something with movies/comics/animation instead).

The good news is that there are legal jobs available that don’t involve practicing law. I’ve worked as an editor for the past three and a half years. I read a lot of cases, true, but I also write articles and design page layouts – two things that I love doing. From what I’ve heard, nontraditional legal jobs are becoming more and more popular with law school graduates. You just have to find one that’s right for you.

Anguish about the past is worthless unless it leads to a change in present behavior.

That said, my few regrets are:

  1. Having Hunter Thompson as a role model. I missed a lot of stuff because I was more interested in the party.

  2. Tammy. When I was 26 I had a 19 year-old girlfriend who was built like a young Marilyn Monroe, bought all her underwear at Fredericks and was madly in love with me. I broke up with her to go back into a relationship with a married woman. :wally

I could have ended up with a beautiful, fun wife.


I wish I’d joined Weight Watchers or Jenny Criag or something 10 years ago. I also wish I’d done a creative work project instead of a thesis for my Masters Degree.

Only regret was that I didn’t look into a broader range of career options. I dismissed a lot of options without much thought. But am I anguished by regret? Nope, I’ve done fine and who knows where I’ll be if I had walked down another road. Maybe better, maybe worse. Living with regret serves absolutely no purpose.

You know, it’s funny you should say this, because one of my regrets (although certainly not my biggest regret) is going to that smaller liberal arts college instead of a bigger state school.

Oh, the classes were challenging and there was more comraderie, but because the college was small my options for majors and concentrations were limited; I wound up majoring in something I didn’t care for. Also, those colleges can get r-e-e-e-al claustrophobic sometimes, especially after you’ve been looking at the same faces day in and day out for four years. I loved my friends, but damn, we were sick of each other after all that time in college. Also, it was a small college in a small town, so you couldn’t really even get away from campus that much. It wasn’t like you had many options besides drinking or Tai-Kwon-Do once you left the school (The locals, by the way, hated college students, and they were not shy about telling us so.).

A larger college would have given me more options on what to study, more outlets for my free time, and a larger number of places to go when I just wanted to get away from it all. Of course, I’m not saying I regret college per se, but sometimes I would have loved to be a small fish in a big pond.

My biggest regret? Not learning math and science when I was a kid and thinking that I was magically going to get it when I hit college.

Oh, and as far as regrets . . . Well, I try to be philosophical about these things. I mean, hey, that’s why they call it “sadder but wiser,” right?