1. Live on your own for a few years
“Getting my own apartment. Moved out of my parents house only after purchasing a house with my wife. Never had my very own place.” — ChaosX422
2. Invest your money
“Investing. Even a few hundred in an index fund would have grown to something quite substantial in the past 25 years. Whatever you can afford to invest, do it.” — ward_bond
3. Be more outgoing and adventurous
“Not being more assertive or outgoing. I was always afraid of imposing on others or bothering them. I think I missed out on a lot of friendships.
People are generally friendly and like meeting new people who like them. I was that way, but couldn’t believe that other people would want to talk to me.
This also killed me in dating. I always assumed that girls were just being friendly, sucked at reading signs, and because I didn’t want to make them uncomfortable or be the guy who forced awkward, unwanted, physical contact I didn’t make moves very often.
So that meant that girls assumed I wasn’t into them or the chemistry just never built.
I also rarely dated outside of dating apps like Tinder or OK Cupid because I didn’t want to ruin friendships by asking out girls I already knew.
Damn, I was stupid.” — WereOnTheEdgeOfGlory
4. Take a few college classes
“I had fun partying, doing drugs, and being wild, but I really wish I’d at least taken a college class per semester to get a head start on things. I’m in my late 20s now and 3 semesters from graduating. It sucks to think I’d be done now if I had even taken one class per semester.” — itiswhatitdotoyou
5. Have a lot of sex
“Having more sex. I married very young to someone I didn’t truly love, didn’t get divorced until my 30s. Now in my 40s I’m enjoying myself , but it would have been a lot more fun if I had the energy and tits of my 20s.” — pamzee70
6. Take care of your mental health
“Slowing down on drinking and taking care of myself mentally and physically. It’s not too late for all of that, I even cut down drinking. But all these vices and lifestyle choices I made routine kind of followed with me and they’re a pain to change.” — MrApproval
7. Stay single for a while to get to know yourself
“Staying single and getting to know myself before getting married. I might have realized my first two husbands were totally wrong for me.” — squeek82
8. Save up your money for the future
“Even just $50/month would have made a difference.” — molleeewrites
9. Make as many friends as you can
“Being more social, making friends, finishing college, having a ton of sex. Now I’m paying for all of that. I wasted my 20s being tied down to someone I’m no longer with. I have kids now. I no longer have the same young hot body so confidence is super low. Definitely wish I experienced more things. Traveled.” — apinkflamingo69
10. Exercise often
“Exercising. I’m 50 and just started last year. It’s hard work, but the payoff is already showing. I was dumb.” — apinkflamingo69
11. Make a life plan
“I regret not having made a life plan, of some type. To give me direction. Instead I followed what others needed of me, taking care of others, and when the time came I needed those same people they dropped me. I regret, more than anything, not having had a goal for myself to work towards. I could have accomplished something, anything while helping others.” — KazDav
12. Travel the world
“Traveling the world more.
I landed a good job out of college and then started making decent money but then burdened myself with debt from a new car, house, etc. Having those things is nice but they combined to lock me down so I couldn’t take a few months to explore the world. There’s so much to see out there and short trips of a week or so at a time doesn’t really give you the chance to immerse yourself into the culture and really get that experience.” — SailingSmitty
13. Party when you get the chance
“Partying more… I was working 8 hours/day and 6 hours I had classes at the university… Now I am 29, I party hard but it’s not the same feeling.” — MITSF
14. Get tattoos and piercings
“Gonna sound stupid, but got a bunch of body piercings. When I was in my early 20s I nearly got a variety of different piercings, mostly to see what they would be like, but always chickened out. Now I’m older and in a professional job I wish I’d just taken those risks, even if I took it out a few months later.” — Jman7188
15. Spend time with your family
“Eating out at all night diners with my friends.” — drewbrown215
16. Wear sunscreen
“Sunscreen. I was never as diligent with it as you should be. And now 20 or so years later I have had skin cancers and ‘suspicious looking’ spots cut off and frozen off my face regularly.” — eleventacles
17. Remove toxic people from your life
“I wish I got toxic people out of my life, and didn’t get dragged down in their shit so much. FYI – if you don’t like someone, you don’t have to be friends with them!” — feeling_daria
18. Make the first move
“Kissing this guy when we stayed up all night talking. You miss all the shots you don’t take. Learned my lesson and never missed a chance afterwards.” — WeedleBeest
19. Stop giving a fuck
“I regret all the fucks I gave. The best thing about getting older is giving less fucks.” — coughdrop01
20. Slow down and actually enjoy life
“Slowing down and enjoying life more. When I was in my early 20’s, I was too much in a rush to grow up, start a career, and start a family. I was too much in a hurry. I was too busy thinking about the future. My early 20’s were probably some of the best years of my life. I just wish that I had taken the time to slow down and enjoy it more.” — sundac
21. Visit the doctor instead of putting it off
“Going to the dentist regularly. It’s no fun catching up on dental work that should have been taken care of years ago.” — BoBot86
22. Get some work experience
I didn’t work at all in my early 20’s and now it’s biting my ass several years later. I graduated college two years ago with zero work experience, and no one would hire me. I’m currently on my third temporary job (which ends in a month), and I have yet to land a full-time permanent position anywhere, let alone in the industry I went to school for (geology). I also live with my mom.
You’ve been warned kids.” — coniferbear
23. Be more social
“Not being more social than I was. Turns out – it’s WAY more important than practical skills when it comes to job hunting AND keeping a job.” — JoOngle