The Biggest Mistake of Your Life - Reddit

“What’s your biggest regret?”

That was the question on Reddit. Thousands of comments poured in—confessions, missed chances, unspoken apologies. I didn’t expect to see myself reflected in so many of them. But there I was, in every regret typed anonymously into the void.

One user wrote:

“I ghosted a friend when she needed me most. She called during her mom’s cancer battle. I panicked, ignored her, and never called back. She never spoke to me again.”

That hit me. I had a friend in college—Naomi. We were inseparable until life got hard for her. Her father died. Then her boyfriend left. She started calling me late at night, crying. I didn’t know how to hold space for that. I avoided the calls. Eventually, she stopped trying. I never called back.

Another comment read:

“I stayed at a job I hated for 11 years because I was scared of not having ‘security.’ Now I have neither the job nor peace of mind.”

I haven’t made it to 11 years, but I’ve been sitting under fluorescent lights in this cubicle for six. Six years of telling myself just one more year, just a little more savings, just until I figure out what I really want. I haven’t figured it out. I just got better at ignoring the question.

Then came this:

“I let pride ruin my relationship with my dad. We didn’t talk for six years. He died before I could say sorry.”

That one stopped me cold. My father and I haven’t spoken in two years. I can’t even remember the argument anymore, only the silence that followed. Pride is strange like that. It swells until it’s the only thing you can see. But it shrinks the second you're too late.

One person said:

“I didn’t apply to art school. I still paint, but now it’s only nights and weekends after a job that drains me.”

I didn’t apply either—not to art school, but to writing programs. I filled notebooks with short stories, poems, unfinished novels. I told myself I’d get back to it once I had a real job, once things were “stable.” But stability is addictive. It makes dreams feel impractical.

And then this:

“I regret not enjoying the little moments when my kids were young. I was always so busy ‘getting things done.’ Now they barely need me.”

I don’t have kids. But I thought of my mom. Of all the times she asked me to come by, to call, to stay a little longer. I always said, “I’m just so busy.” Busy doing what? Busy avoiding regret by building a life I wouldn’t want to escape. Funny how that turned out.

Regret isn’t always a firework. It’s not a dramatic collapse. It’s quieter than that. It’s the email you never sent. The friend you never checked on. The thing you said you’d do “when the timing is right.”

Most regrets aren’t about what we did.

They’re about what we didn’t do.

And those are the ones that echo.

Now To Lighten The Heart, Here Are Some Funny Ones

• "I told my cat he was adopted. He knocked my glass off the table and walked away. So I guess we're even."

• "I tried cooking like Gordon Ramsay. Burned the food, yelled at my wife, and cried in the shower. Nailed it."

• "Dating apps are wild. I matched with someone, we both swiped right... and then he messaged me: 'I meant to swipe left.'"

• "Told my boss I was feeling 'spiritually unwell' and couldn't come to work. He just replied 'same' and told me to take the day."

• "I bought a smart fridge. It now emails me when I'm out of cheese. I'm being cyberbullied by a fridge."

• "My toddler just asked me if dinosaurs had moms. I said yes. Now she's crying because she thinks T. rex didn’t have enough hugs."

• "Was on hold for 45 minutes. The music stopped and I got excited. Then it looped back. I aged 3 years in that moment."

• "My dog barked at his own fart and then left the room like it was my fault."

• "Told my therapist I procrastinate. She said to try journaling. I’ve been meaning to start a journal for three years now."

• "Someone said I dress like a divorced history teacher. Joke’s on them—I teach math."