20 Things People Over 40 Regret Not Doing When They Were Younger

We’ve all heard the saying, “Youth is wasted on the young,” and let us tell you, those over 40 have some stories to share. They’ve been there, done that, and now they’re sipping on their coffee, thinking about the things they wish they’d done when they were still young, wild, and free.

One Redditor asked, “People who are 40+, what do you regret not doing when you were younger?” Thousands of users shared these laws and we have compiled the perfect list for you!

1. Bad Relationships

The over-40 crew is practically throwing a parade for those who can cut ties with toxic exes and not get stuck in dumpster-fire relationships.

A discerning Reddit user commented, “Getting over exes/staying in stupid relationships. In retrospect, so many people to meet; spending time unhappy or sad over break ups, what a waste of time that you don’t get back.”

Another replied, “Good point, and I’ll expand. Sometimes, you think that you may not meet someone new that you’re compatible with, someone nicer, better looking, etc. You absolutely will. There are so many new people and opportunities out there.”

2. Dental Hygiene

Teeth, people, teeth! The over-40s wish they’d been on a first-name basis with their dentist.

Someone commented, “Taking better care of teeth.”

Someone else added, “Yes! This. And making sure my dentist wasn’t a quack. He hollowed out my teeth even for a tiny filling because why not? So I did go to the dentist, but the work he did is collapsing now and costing a mint.”

3. Friends

A Reddit user wrote, “Making more friends and staying in touch with old friends. It gets so much harder as you get older.”

“I’m good at keeping in touch with friends, but I have a hard time getting anyone to hang out more than once or twice a year as everyone acts like I’m asking too much of them or being clingy. It has to go both ways. I can’t keep one-sided friendships going for very long.”

It’s not a popularity contest, but the over-40s are dropping truth bombs about the importance of having a solid crew.

4. Saving Money

A discerning Reddit user commented, “Save your money! Stuff those 401ks, IRAs, HSAs, and 529s!”

Another replied, “Yep, wish I would have opened a 401k or something when I first started working. My company is small and doesn’t offer one, but I really wish someone would have said hey, you need to retire.”

Skip the impulse buys, ditch the daily Starbucks habit, and put those dollars into a savings account.

5. Life Plan

Someone commented, “Making a plan for a life past 30. I lived life to the extreme with the motto of “live fast, die young, and leave a good-looking corpse.””

Someone else added, “Yeah, ever since I turned about 28, I stopped thinking in terms of decades out but rather the next year. It felt like I didn’t expect to be around after the next 2 years. I’m still doing this at 33. I have no idea what I will be doing at 36. It almost felt like I was hoping to be dead before that time came to be.”

Plan for a future that’s not just about paying bills and adulting; it’s about living your best life.

6. Traveling

The over-40s are practically begging you to grab that backpack, book that ticket, and embrace the sweet chaos of wanderlust. Your future self will high-five you for those epic travel tales.

A Reddit user wrote, “Not traveling more when they were younger. Discovering other cultures, making new friends, and gaining fresh insights can all be accomplished through travelling.”

Another added, “I’m thinking of going back to my seasonal job so I can have a few months to travel. I’m 24, and should be looking at a full-time career. But, I know years down the line I might regret not seeing all the countries I want to see, backpacking, and meeting new people.”

7. Toxic Family

A discerning Reddit user commented, “I regret not getting away from toxic family faster, getting their tentacles of negative/unhelpful thought out of my head. Just working more, saving more, so I’d have more security now.”

Another replied, “I feel this. I also steer clear of negative and toxic people. If their energy affects my peace, bye-bye then.”

Yeah, yeah, family is family, but sometimes you have to drop the dead weight. Don’t let toxic vibes hold you hostage.

8. Dating

Dating, oh sweet dating – a dance of romance, missed connections, and awkward encounters.

Someone commented, “Dating, I wasted my youth working. I didn’t start dating till I was well in my 30s when I finally started dating; so far, no luck, but I’m not giving up. I’m sure I’ll find someone someday.”

Someone else added, “Thank you for saying this. I needed to hear this, as someone who just turned 38 and has had no luck in finding love yet.”

9. Partying

A Reddit user wrote, “I regret not staying sober more. Partying is great, but everything in moderation… I regret not trying to get into my career field earlier.”

Another replied, “I really regret all the money I spent partying. Which, like you said, isn’t saying to NEVER party, but I was out every weekend more out of a feeling of obligation and not wanting to seem lame than actually having fun. I don’t even talk to any of those people anymore. I have nothing to show for all those nights out.”

Balance those crazy nights with some chill ones. Your liver, your wallet, and your future self will thank you for not turning every weekend into a scene from The Hangover.

10. Stretching

A discerning Reddit user commented, “Stretching. Wake up every day with back pain due to tight hamstrings, flexors, and shoulders.”

Another added, “No reason not to start now. I’m 43 and still stretch, and it relaxes all the places that hurt enough for them to stop.”

So, do those stretches, touch those toes, and embrace flexibility like your body depends on it—because it does.

11. Confessions

Someone commented, “Telling her how I felt.”

Someone else added, “Oh man. I still carry a torch for a girl I met when I was 18. I’m 64 now. We were friends for about 20 years.”

In the future, you will either be grateful for the romance or appreciate the closure.

12. Sleep Schedule

Now, the bad sleep schedule saga. Oh boy, the over-40s are practically rolling their eyes at their younger, night owl selves.

A Reddit user wrote, “Going to bed at a decent hour and starting my day before 6 am, doesn’t matter what I’m doing whether it’s working out, stretching, meditating, or reading or whatever (not phone time).”

Another replied, “Starting a morning routine has helped me in so many ways accomplish more in my days. Especially mornings. It was not easy, but it stuck after a few months.”

13. Investing

Someone commented, “Investing in real estate.”

Another replied, “Investing in Google – one of my professors suggested it when they went public. I didn’t feel I could afford it. I guess not taking more chances generally.”

So, get yourself a piggy bank, a stock app, or whatever suits your fancy, and let that money grow!

14. Drinking

A discerning Reddit user commented, “I wish I’d stopped drinking alcohol way sooner.”

Someone else added, “Yeah I’m 32 and have the same regret. Better late than never though I suppose…”

Sip, don’t chug, and maybe opt for water between those shots!

15. Having Kids

The over-40s wish they’d thought twice before jumping on the parenting roller coaster. So, before you dive headfirst into parenthood, think about it.

Someone commented, “Having a kid, prob not gonna be a popular answer, but I had one when I was 39, almost 40. Will prob have 2nd when I’m 42. The idea that when they’re an adult, I’ll be 60 and not get to see a lot of their adulthood is a huge bummer. I wish I had one mid-30s at the latest; life moves so fast.”

Another added, “I was 43 when my son (am 64 now), so I know what you mean. The thing is, I was a lot more grounded when I was 42 than when I was 30. That extra 12 years gave me a ton of life experience I didn’t get a chance to get when I was in my 30’s. I made a lot of mistakes back then and am thankful I got those out of the way before he was born.”

16. Sunscreen

A discerning Reddit user commented, “Not wearing sunscreen on a daily basis.”

Another replied, “Not only did I not wear sunscreen, when I went to the pool or the beach, I lathered myself with tanning oil. I’m sure that will come back to bite me.”

Turns out, those golden tan dreams come with a side of wrinkles and sunspots!

17. Being Diagnosed With ADHD

Someone commented, “Getting my ADHD diagnosed.”

Someone else added, “I feel you! I’m 52; it took them 20 years to figure out I am schizoaffective. Now, I suppose it’ll take them years to decide if I’m on the spectrum or not. I hope you’re okay now, though. Hope they’re looking after you. Some of us repeatedly fall through the cracks in the mental health services.”

So, schedule those appointments, get those screenings, and keep your body in check.

18. Taking NSAIDs

The over-40 crew is sharing some stomach-churning tales of taking painkillers on an empty stomach.

A Reddit user wrote, “Never taking NSAIDs (Aspirin, Advil) with food. I didn’t ever abuse them or even take them more than a few times a month, but give it 30 years, and that’ll create an ulcer!”

Another added, “I did abuse Advil for pain relief (was suffering from gout). That ended up wrecking my kidneys. Currently at Chronic Kidney Disease 4, which is one level away from dialysis or transplant.”

19. Not Being Single

A discerning Reddit user commented, “Being single longer. It would have been nice to live life on my own terms for a while.”

Another replied, “Same. When I was married to my (ex) husband, I would fantasize about having my own place again. Now that I’m re-married, I don’t have that fantasy anymore!”

So, take a breath, enjoy the single shenanigans, and let your future self appreciate the freedom before the joint bank accounts and shared chores kick in.

20. Have Fun

Someone commented, “Take adventures in your 20s. Borrow the money, take what’s offered, and pitch parents and family on the adventures you want to take. You’d be surprised who will support your adventures. Your 20s are the magical years where you’re typically broke but also the most free of responsibility you’ll ever be. Most of your peers are in the same boat. Take advantage of this time by doing as much as you can.”

Someone else added, “Best advice I’ve read here so far. I had so much fun in my 20s. I tell my 20-something co-workers all the time to have a blast and do all the things they want to do. They still have the energy and drive and time.”

Your future self will cherish the memories of those wild, carefree moments.

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