What’s your biggest regret of your 20s?

What’s your biggest regret of your 20s?

What do you think?


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  1. Generally just not doing things. Take chances, experience new things, put yourself out there. Better to fail sometimes then look back with regret and wonder “what if?”

  2. Didn’t spend enough time with friends. Not hanging out on the occasional weekday. Not asking out a woman I met who gave me her phone number and said we should hang out more after we met one night and just had the best time.

  3. Graduated university with an average GPA, I’m in a job and industry I don’t like, never had the confidence to start dating (met my first girlfriend when I was 29 last year but we recently broke up), not being in great shape, and barely traveled (partly because of quarantine)

  4. My biggest and only real regret in my whole life was allowing myself to cheat on my ex and the love of my life. I do truly regret and many times wish I could go back to stop myself from doing what I did.

  5. I wish I had lived with more integrity and treated the people around me better. I hurt and disappointed some good people during that time which I have come to regret a lot. Luckily I still have some good friends, but I’m embarrassed sometimes.

  6. Getting so obsessive and ruminating about heartbreak that I didn’t take enough time to meet some of my goals and have as much fun as I should’ve (I did have some fun though)

  7. Dating anyone, I wasted a lot of time dating immature people who were very toxic. I would have been much better off not dating and wasting my money on others and instead just busting my ass at some random hands-on job saving every penny I could get my hands on and buying a home. Then once settled in a home I owned not rented try out getting to know people and getting to know people much much slower. Though being as how I met my current GF who has been the longest relationship of my life for over 3 years IDK if doing anything different would have made me miss that chance to meet her or not so maybe I would not change anything.

  8. Not investing.
    Worrying about women.
    Worrying about finding a job.

    I wish I knew how many people were supporting me and helping out that I was completely oblivious to. Some people I have been able to reconnect with and say thank you, the others I say thank you by paying it back by helping others.

  9. Mine aren’t over yet, I have a couple years left. But I really wish I started losing weight earlier. I didn’t start getting my shit together till I was almost 26, and I spent 20-26 eating/drinking myself into an early grave. But I’m thankful I caught on early enough and I’m making changes before I’m way older, because I can only hide bad habits behind the veil of youth for so long.

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