We Asked 100 People to Tell Us Their Biggest Regret
We asked 100 people one question:
“What is your biggest regret?”
The answers ranged from specific financial mistakes
to deep emotional wounds regarding family and lost time.
Here are the regrets they shared.
Personal Identity & Choices
- I wish I came out earlier, but I was too scared.
- I regret that I wasn’t in the military during 9/11.
- Not getting mental health help sooner.
- I wish I got in a better habit of flossing.
- Buying a 1984 Toyota Cressida ($5,000 down the drain).
- Not standing up for myself more as a young woman.
- I wish I had told somebody I used to work for to just f*** off.
- I regret getting into the car with my ex-husband (he drove into a tree).
- I don’t believe in regrets.
Relationships & Romance
- Cheating on my kid’s mother.
- Getting into a relationship with a married man.
- My baby’s father.
- I wish I would have met the love of my life forever.
- Not having a relationship with a specific gentleman I met (Reggie).
- A specific one-night stand (he kept his hat on during sex).
- Getting married early.
- My marriage (ended in a painful divorce).
- Staying in a relationship that was toxic.
- Taking back an old boyfriend.
- Dating men.
- Having sex so young.
Family & Parenting
- Going to prison when my daughter was two.
- Telling my mom that I hate her.
- Partying a lot when I should have spent more time with my kids.
- Not saving more for my kids’ education.
- Not being very present in my daughter’s lives.
- Not listening to my dad.
- Running away from home when I was 16.
- Living recklessly.
- Not talking to my father more before he passed away.
- Not learning more Korean at a younger age to talk to my immigrant parents.
- Not seeing my family for years.
Substance & Legal Issues
- Getting as drunk in college as I did.
- Not getting sober sooner.
- Getting plastered at my sister’s wedding.
- Going to a specific house party at 17 (blacked out).
- Ever smoking a cigarette.
- Smoking weed.
- Texting and driving.
- Drinking and driving (lost license and did jail time).
Past Behavior & Bullying
- Any time that I’ve hurt somebody.
- Making a nasty racial reference to another kid in grade 8.
- Bullying a girl into stepping in dog poop barefoot.
Education & Career
- Taking French instead of Spanish in high school.
- Falling in with the wrong crowd in high school.
- Being homeschooled.
- F***ing up high school.
- Getting “stuffed like a chicken” in basketball and not having a comeback.
- Not continuing college.
- Going to college.
- Not becoming a doctor.
- Not going to nursing school.
- I wish I continued playing soccer.
- I wanted to sing opera (but didn’t).
Location
- Not getting out of my hometown sooner.
- I wish I would have stayed in Maui.
- I regret moving to Seattle.
Loss & Grief
- Not going over to my best friend’s house right after work (he passed away shortly after).
- Not being strong enough to hold my daughter when she died (pre-term labor).
- Not being there with my family when my sister passed away.
- Not spending enough time with my brother before he passed away.
