What’s your biggest regret of your 20s? by QuestionGuy September 7, 2022, 11:43 pm What’s your biggest regret of your 20s? What do you think? 1 Point Upvote Downvote 20sAskAskMebiggestQuestion and AnswerregretWhats See more Previous article TIL Paris, Texas has its’ own Eiffel Tower, which is wearing a red cowboy hat. It is a scale model, standing at 65 feet tall. 35 Comments Leave a Reply 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?” Log in to Reply 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. Log in to Reply Spending almost all of it wading in depression and anxiety. My 30s have found me with much more confidence. Log in to Reply Not making a move on Liz. Log in to Reply Being in a serious relationship from 22-27 Log in to Reply Getting married Log in to Reply Not investing a lot of $$$ in Corning Glass when my father-in-law told me to. Log in to Reply Not working hard enough and planning for future. Log in to Reply Losing contact with a girl I was really into and not getting married by the time I hit 30. Log in to Reply Caring way too much about what people thought of me. I feel like I wasted so much time being worried about dumb shit. Log in to Reply feeling jammed Log in to Reply I was arrested for cocaine possession very shortly after my 21st birthday… that kind of sucked. Log in to Reply Not exercising or eating better Log in to Reply Definitely my suicide attempt. I should have picked a less boneheaded and flawed way to do it. Log in to Reply Too many video games, not enough pussy. Log in to Reply Getting married. Too young. Log in to Reply My first wife. Should have waited. Log in to Reply Financial stupidty that I have learned from and tried to teach my kids about so they don’t follow Log in to Reply 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) Log in to Reply 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. Log in to Reply Nothing. Had anything been different, I might not be where I am now. Log in to Reply Not losing my virginity sooner. Log in to Reply Getting a masters degree Log in to Reply Should have done more drugs, not as fun when the hangover lasts a few days now. Log in to Reply 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. Log in to Reply Drinking. Ugh, how embarrassing looking back on behavior when drinking. I am just thankful it was before everyone had a camera on them. Log in to Reply 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) Log in to Reply Going into sales. I used to enjoy it for many years, but now in my mid 40s, I wish I had done some things differently. Very very differently Log in to Reply Working too much. Log in to Reply I don’t regret anything Log in to Reply Much to soon to be asking that. Log in to Reply Not taking photos or documenting my adventures. Log in to Reply 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. Log in to Reply 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. Log in to Reply 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. Log in to Reply Leave a Reply Cancel replyYou must be logged in to post a comment.