Like all things in life, regret has a great Ben Folds song written about it. Actually, a lot of his songs center around regret, come to think of it, but the one that’s actually just straight up called regrets includes evocative passages like:

I thought about sitting on the floor in second grade
I couldn’t keep the pace
I thought I was the only one moving in slow motion
While the other kids knew something I did not
But if I acted like a clown
I thought it’d get me through, it did
But that don’t work no more

What is something you have always regretted doing? from AskReddit

Of course, regrets really go far beyond just general musings about where we’ve been. Sometimes they are concrete and brutal instances, like the ones Reddit decided to share.

1. Brush your teeth

Dental hygiene. Had braces as a teen and neglected my teeth for the 20 years after except for yearly cleanings.

Too many mountain dews and too many days of “I’ll just brush my teeth tomorrow” turned into cavities and peeling enamel.

You don’t appreciate teeth not hurting until they are.

– Garbmutt

2. Toxicity

Wasting my time on toxic friendships. Never again.

I also regret not ending my first relationship when I first wanted to (after year 1 instead of year 8…)

– aquanite

3. Job stuff

Not doing internships in the summers during law school.

Instead, I went straight through and graduated in 27 months.

It was a mistake that limited my ability to get a job after graduation.

– MarbleousMel

4. Care for your body

Not listening to my doctors warnings and not taking care of my diabetes from 15-25.

Since March last year I have had an op to restore vision in my right eye, an op to do the same in my left, an op to reattach the retina in my left eye and currently waiting to have another in my right eye to restore vision and an op to remove the silicon oil that is currently holding the retina in my left eye in place.

Was completely blind for 2 months and only now have a small amount of vision in my right eye. The left eye has just enough vision for me to walk around without hurting myself until the oil comes out.

Listen to your doctors kids.

– IronSkywalker

5. All for a girl

Quit a college program for a girl. Just stopped showing.

It wrecked my grades and took forever to be complete my degree after

– ludoludoludo

6. The man at the repair shop

I work at a small, retail family business (repair shop). This older guy we didn’t know kept coming in to hang out with us, probably 4 or 5 times a week. We thought it was kinda weird, but we were fine with it, he’d just hang out in the back with us and talk for 30 minutes.

This kept on for maybe 6 months, he kept trying to hang out with us outside of work, seemed kind of desperate. Most of us turned him down respectfully. I turned him down because I was like 25, and he was 55.

He starts buying everybody really expensive gifts. He came in with a 2,000 dollar AR-15 as a present for me (I used to be into guns). I turned it down because I didn’t think it was right to accept it. Most of the people there turned down his gifts. This seemed to really upset him, and he stopped coming around.

About a month later, we got a call – can’t remember if it was from his lawyer, family member etc. He’d had terminal cancer for the past year, and he had finally died. He’d hidden this from all of us.

So, he was just trying to make new friends before he died, we mostly turned him away because we thought he was weird and desperate.

Biggest regret of my life.


7. Look into it

I regret not doing a fuller investigation of career options before going to college or making the effort it would have taken to change course mid-career.

I just retired from a career that was satisfying but probably not my best match.

– moinatx

8. Marriage woes

Marrying the wrong person.

Be sure you really know who you are marrying. The family. The friends. The acquaintances. When they’re angry, sad, happy. How they spend money. How they save money.

Because you could end up like me – 31 years unhappily married. And we have a special needs daughter who needs us together in the same house for reasons I can’t go into here.

So I’m locked in, and so is she.

Learn from my mistake.

– Eye_Doc_Photog

9. Cat’s in the cradle…

Not spending a lot of time with my dad.

He died when I was 18 and before that I was “too cool” to hang out with him much.. I regret it so much now.

He technically died from kidney failure after 20+ years with a heart transplant. I ended up needing a heart transplant 2 years after he died and had no one that could relate to what I was going through…. because he was gone, and I never talked much about his transplant with him.

He also never even came to my high school graduation cause he was working so he never really got to see me accomplish anything in life.

I was just a stupid teen that was too cool to hang out with my dad, even though we did so much together when I was a kid.

I miss him everyday, please spend time with your parents and loved ones you never know how long they’ll be there.

– v-rok

10. Saying goodbye

My favourite aunt got diagnosed with liver cancer, she was hospitalised for months but I only visited a few times because it killed me seeing her so weak and full of tubes, I honestly thought she would recover but she died on the operating table and I never got to say my goodbyes.

– Cooshtie

11. Just missing out

I’ll go to conferences or collections of study sessions or something, and I’ll be like, “I’m going to go to x.” Then, when x comes along, someone will ask me, “So, you coming to x?” And I’ll be like, “sorry, but I’m busy,” when I’m probably doing nothing.

I always regret it.

They’re always really interesting sessions with people I would have wanted to meet and learn from, and what did I accomplish from not going? Nothing.

– RandomStranger18

12. The list

Regret not taking school more seriously and getting better grades.

Regret not staying out of trouble.

Regret not being smarter about money.

Regret never living alone.

Regret spending too much time with an ex and not enough time developing strong healthy female friendships.

– Italiana47

13. Fighting it out

I don’t like to say regret, because I did learn from the experience, but I got kicked out of school and sent to jail for fighting.

It was day one of the Phlebotomy program.

– Skyezah7441

14. Animal cruelty

When I was a child discovering the world in the garden, I figured it would be cool to find out what happens if you cut the eye stalks off a slug.

Thought it would be a groundbreaking science experiment, turned out to be a harsh lesson in empathy.

– DilatedSphincter

15. No parting gracefully

There was a time when I did not know how to break up. Interpersonal relationships is hard. It’s hard to start a relationship in particular, but the hardest thing is to exit a relationship as gracefully as you can.

Sometimes you can’t part gracefully, and you have to be able to accept that too.

– juicius

Lessons to be learned all around.

What’s a regret you can’t let go of?

Tell us in the comments.