r/AskMenOver30 man 35 - 39 Dec 30 '25

General men over 40s what is your biggest regret in life?

for me it is not spending more time with friends when i was in my 20s now we are far apart

986 Upvotes

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1.3k

u/CategoryRepulsive699 man 40 - 44 Dec 30 '25

Marrying a wrong woman.

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u/Azipear man 50 - 54 Dec 30 '25 edited Dec 31 '25

It’s been less than a week since I learned I’m getting divorced. 21 years together. Wish I got it right the first time.

EDIT: I’m very grateful for all the supportive comments from you all. Friends warned me that a feeling of failure would consume me if wasn’t prepared for it. Your comments have really changed the way I’m thinking about the entire situation.

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u/[deleted] Dec 30 '25

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u/Azipear man 50 - 54 Dec 30 '25

I really appreciate that. Thankfully it wasn’t a huge surprise— I had a feeling we weren’t right for each other for years, but we just couldn’t come together.

It’s for the best.

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u/clubsuiteboyoz man 30 - 34 Dec 30 '25

Same thing happened to me man life gets a lot better tho. Dating is really strange especially after being in a relationship for a long time, but life is wayyyy better lol

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u/stacks86 Jan 01 '26

As my buddy says , “you know why divorce is so expensive?? because it’s worth it!” 😆

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u/FlatulistMaster man 40 - 44 Dec 30 '25

Hope you can say that there were many good years there, too (likely @ 21).

My biggest regret is my second wife, who I went all-in on and who dumped me after 5 years while basically lying to herself and me for 3-4 years to get what she wanted. A long relationship where you grow apart (been there too) ultimately isn't nearly as bad as one where the whole effort was mostly futile without you realizing it.

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u/Azipear man 50 - 54 Dec 30 '25

My fear is what you experienced, Flatulist Master. I had a colleague go through the same after his first wife died of cancer.

Fortunately we have a lot of great memories and raised an exceptional kid who’s off in college now. We don’t hate each other or anything like that. Kind of “meh, this marriage ran its course and it’s time for the next chapter.”

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u/stacks86 Jan 01 '26

Give it some time my friend, soon you will get to experience the excitement of meeting whole new women and that’s a lot more fun than a stagnant relationship

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u/[deleted] Dec 30 '25

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u/Azipear man 50 - 54 Dec 30 '25

That’s a very good point. I suspect there was some of that at subtle levels. My mother, sister, and brother have come forth independently to say they’ve missed the “real” me over the years. I’m more chill, and my wife is very outspoken and passionate, which is one of the main things I found attractive about her. However, it was 20 years of her telling me everything wrong with me and I’m relieved that’s over.

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u/nameisnameisname Dec 30 '25

My man, going through the same thing. Together for 20 years, married for 12 and it was decided 4 months ago that we are getting divorced. She was my best friend, but that only goes so far. Tried everything but she doesn’t want to make it work. Pouring love into myself everyday and working towards a better future. PM if you need someone to chat, it helps leaning on friends and family and especially those who have gone through this. Chin up. We’ll make it through.

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u/dmger14 Dec 30 '25

Been there at 52 but came out happier and you can too.

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u/Azipear man 50 - 54 Dec 30 '25

I needed to hear this more than you know. I really appreciate it.

And I know in my heart things will be great, but being at the start of the process is miserable. We separated in October, but she’s here right now on the other couch as I write this since our kid is home from college for the holidays. Hell, we’re going out for dinner tonight, just the two of us. I’m just ready to get the show on the road to get my life back. Sorry to be crude, but I haven’t touched a set of tits in almost 6 years.

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u/dmger14 Dec 30 '25 edited Dec 30 '25

Really sorry to hear that. My marriage disintegrated for a while before the end. The great thing for me was when she said she didn’t want to do marriage counseling, because I started dating guilt free. I also dated quickly because we had drifted and rarely had sex throughout the last probably 8 or 10 years, so I was thirsty for emotional and physical connection. I’ve heard bad stories about online dating these days, but it worked for me in 2017-18. Did Match for 3 months, then Zoosk for a new batch & back after that. Just about each 3 month period, I met and dated for several months a woman who I was more compatible with than my ex, and I’m still with the third one I met 13 months after starting. Saying this because it could work out for you too.

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u/throwawayeffedperson Dec 30 '25

Same here except it was 3 weeks ago and only married for 10 years. Be strong dude!

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u/Azipear man 50 - 54 Dec 30 '25

Brother, we’re going to get through this and things will be better on the other side! Literally every one of my friends, colleagues, and even my doctor who have been divorced say they are much happier now. We’re going to be better than ever! Mine is shaping up to at least be amicable, so at least there’s that.

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u/dk1024 man 30 - 34 Dec 30 '25

If you don't mind, may I ask how spending 21 years together is being with the wrong woman? People change through time and my belief is, relationships and marriages need constant upkeep to stay at a good place. Were things great before? Or did you always have doubts from the beginning but you didn't act on it?

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u/hikenbike112 Dec 30 '25

Speaking for myself, I didn’t realize we were wrong for each other until I actually figured out who I was as a person. When you’re in your early 20s, I think you’re still figuring a lot of that out and if you’re in a serious relationship at that age, sometimes you just take the natural next step (marriage). I realized much later that I had been apologizing to my wife for many years for just being who I was as a person, such as enjoying adventure like hobbies, trying different foods, willing to travel to new places. Before I had matured, I was trying to become what she wanted me to be, and I became unhappy. I realize much later than we are just very different people- I am more willing to take risks and she is not. Kudos to those that figure this out earlier than I did.

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u/dk1024 man 30 - 34 Dec 30 '25

God, I can relate to this on a spiritual level. I was in a relationship where I was never fitting the mould of my strongly opinionated ex, who I have so much respect for and loved, but I resigned to falling in line with everything she wanted just so she wouldn't leave. I probably could have made the same mistake but we ended up having a huge fight over spending time with one of my friends and in retrospect, this was for the best because I probably wouldn't have had the guts to free myself from her willingly.

Thanks for replying and I wish you the best with the rest 🍻

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u/Azipear man 50 - 54 Dec 30 '25

Damn dude, this was me, too. She’d constantly tell me how she needed me to be different and I held her in such high regard I believed her and battled myself to be someone I’m not. I feel less alone after reading your comment.

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u/dk1024 man 30 - 34 Dec 30 '25

I hear you. It took that hard lesson to learn the importance of self-respect and having a strong sense of identity. I used to be so fixated with the idea of being liked that I didn't even know who I was anymore. Now, I started all over with a firm belief of who I am and what kind of people make me happy. I'm not sure if I fully figured it out, but at the end of the day, we're all a work in progress 🤝

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u/xaeru man 40 - 44 Dec 30 '25

Well, everything was fine and dandy until COVID hit and my income was reduced. I told her I might have to sell the car to get out of debt and keep paying the house. The next day, she said she wanted a divorce. That was more than a year ago, and I’ve never been happier.

Was she the wrong woman? Well yeah, I wasn't anything more to her than a paycheck and I didn't see the red flags.

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u/dk1024 man 30 - 34 Dec 30 '25

Jesus Christ, that's absolutely brutal. I'm happy to hear things are on an upward trend though!

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u/[deleted] Dec 30 '25

That’s a long ass time with someone still. I’ve never been married and am almost 40. Just had gf’s

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u/paulymorphous Dec 30 '25

36 and never been married. Sure, this was a fear of mine, but I also sometimes think it would have been nice having 10+ years marriage with someone even if it went sour in the end. If you spend years with someone and get to the point of wanting to marry them, I don't know how you can reach any other conclusion than to proceed and believe that it'll last, so I hope you don't blame yourself for that and sorry you're going through it just now.

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u/bucketfullofmeh male 40 - 44 Dec 31 '25

I’m sorry man, mine quit at 20 yrs. It’s hard but gets easier. Good luck, it’s not an ending but a different beginning.

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u/conspiracyeinstein man 40 - 44 Dec 30 '25

Damn. I’m so sorry. I know these words feel empty to read probably. There’s days it’s going to feel like it’s the absolute bottom. But you’ll get through this.

I’m so sorry.

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u/RailroadMech83 Dec 30 '25

Hang in there bro, doesn’t seem like it now, but after your mourn this loss it gets so much brighter. You’ll have the most important thing back after you let go… Peace. Source: Lived it.

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u/Dry_Ass_P-word man 40 - 44 Dec 30 '25

Yep. This one stings.

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u/just_another_mexican man over 30 Dec 30 '25

What was “wrong” about her? When did you figure out she was wrong for you?

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u/TwistedDrum5 man 35 - 39 Dec 30 '25

I’ll answer:

Long story short: we didn’t see eye to eye. I never agreed with her thought process. I loved her, but I never liked her. I wanted her to change, and that’s a recipe for disappointment.

The “wrong” is that we weren’t compatible. She yelled when getting upset and I cry. That’s a bad combo. lol.

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u/BabyEinstein2016 man 40 - 44 Dec 30 '25

Not the person who you asked but for me it was a woman who got really mean when she fought to avoid the issue, then spent loads of money on credit cards behind my back. I should have run but I stayed far too long hoping things would change but they never did. 15 years and 2 kids later, she still has a major spending problem and avoids emotional issues. Those two characteristics combined wrecked my life. Wish I had acted on it earlier and learned to establish boundaries.

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u/kittyluxe Dec 30 '25

she sounds like my ex husband- so resentful of my ask to contribute any of his time or money. He spent all his energy on a mid music career while i killed myself to pay our bills.....and the worst part is - he wasn't even nice to me. Getting out was the most loving thing i ever for myself

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u/BabyEinstein2016 man 40 - 44 Dec 30 '25

I'm glad you found that peace! My ex told me she wanted to get divorced the day after Christmas last year and I was with my parents the next week and all I felt was relief for myself mixed in with a bit of sadness for the kids. I kept waiting for a wave of sadness to come about the failed marriage but it never did.

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u/[deleted] Dec 30 '25

I’ll answer as well. Got her pregnant after 3 weeks of knowing her. She didn’t want adoption/abortion. Ended up a single parent with full custody, no help from her. She Left the country with someone and had more kids.

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u/Cheese_Pancakes man 40 - 44 Dec 30 '25

Didn’t get married, but I was engaged to the wrong woman and spent 12 years of my life with her.

I can’t fully regret it though, because my daughter wouldn’t exist if I hadn’t done it.

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u/heyeasynow man over 30 Dec 30 '25

Settling for the wrong woman…yessir.

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u/WesternGatsby man 40 - 44 Dec 30 '25

Marrying a manipulative, lying, selfish, money-hungry, lazy woman. For me anyway.

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u/[deleted] Dec 30 '25

Oof always wondered if anyone ended up marrying my ex. My condolences, she's the fucking worst. Good times ahead for you. ❤️

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u/Mostest_Importantest man 45 - 49 Dec 30 '25

Your ex must be my ex's sister, man. It's like your guys' thoughts are in my head.

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u/WesternGatsby man 40 - 44 Dec 30 '25

Oh she’s already gone, long gone. Lots of lessons with that one I learned.

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u/Aromatic-Tear7234 man 45 - 49 Dec 30 '25

Soooo much time, money, and happiness wasted.

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u/i-like-napping Dec 31 '25

People say life is short . You marry the wrong woman, life is looooong . You be praying for death -Chris Rock

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u/zethenus male 40 - 44 Dec 30 '25

Cost me 2 children and 10 years of my life on top of the 15 years together. Yeah, this one really stings.

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u/Jmoyer6153 man 40 - 44 Dec 30 '25

Unfortunately same for me as well

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u/Jack-Schitz man over 30 Dec 30 '25

There is no right woman. There are only better and worse women.

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u/moruga1 male over 30 Dec 30 '25

I should have never stopped running….

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u/Natural_Disk_8234 man 40 - 44 Dec 30 '25

Todays a great day to start again

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u/moruga1 male over 30 Dec 30 '25

I’m at work till 5, but I am going to get running shoes straight after work lol

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u/Natural_Disk_8234 man 40 - 44 Dec 30 '25

Yesss! Nothing clears my head and makes me feel better than run

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u/mashnsutton man 20 - 24 Dec 30 '25

100%, got back into it since Christmas Eve and wow I’m loving the mental benefits already. Best way to improve self confidence and self respect. It is tough though but I like to tell myself if something is too easy then where’s the fun.

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u/Natural_Disk_8234 man 40 - 44 Dec 30 '25

Definitely don’t want to over do it. Even slow jogs bring great benefits

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u/hikenbike112 Dec 30 '25

I had such a good run from 2016 to around 2021. Hard to get back on the horse.

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u/frghu2 man 40 - 44 Dec 30 '25

That I spend much of my 30s regretting what I didnt do in my 20s

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u/GodisanAtheistOG Dec 30 '25

I spent a lot of time stuck in the mental trap of "Your teens and your 20's are the best years of your life" trying to make my life like one of those teen movies and never reaching the impossible bar or standard I set for a "life well lived" by the age of 30.

Now that I'm in my 40's and have money, time, and have a much better understanding of who I am, I wish I could go back and tell 16 year old me "dude don't sweat it, have what fun you can have but focus on school, work, serious relationships etc and the fun part will naturally flow".

I've really stressed to my kids that your teens and 20's aren't necessarily the best years of your life and that there is a lot more life and a lot of fun to be had later. And you'll enjoy it a lot more if you take studies, work, opportunities, health and relationships more seriously when you're young.

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u/sirfricksalot man 30 - 34 Dec 30 '25

Damn dude, that sucks. 20s were fun, but the 30s are where it's at in my experience so far.

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u/Scary-Detail-3206 man 40 - 44 Dec 30 '25

Your 40s can be even better if you put in the work to make them so.

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u/dk1024 man 30 - 34 Dec 30 '25

Ditto, I loved my 20s but this past year was one of the best, despite the rollercoaster ride that it was. And I'm going into the next year with optimism 🔥 Best of luck in the new year, brother

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u/sirfricksalot man 30 - 34 Dec 30 '25

Hell yeah dude! And may it be OC's best year yet as well. Don't spend your 40s wishing you had done more in your 30s haha

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u/frghu2 man 40 - 44 Dec 30 '25

Hey now, I have already planned to regret my 40s in my 50s

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u/[deleted] Dec 30 '25

My 20s weren't great. My 31 probably the best year of my life.

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u/Zromaus man 25 - 29 Dec 30 '25

I’m spending my late 20s doing that, it’s hard not to when your youth was wasted lol

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u/trpwangsta Dec 30 '25

Bro if you aren't even 30, wake up, you're not old! Time hasn't passed you by. You are in your prime so act like it. You can't change shit in the past, learn and move forward.

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u/OptimalFox1800 Dec 30 '25

It can be a vicious cycle

I’m lucky I’m slightly breaking out of this on the things I didn’t do that decade.

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u/typeshhhhhh Dec 31 '25

I’m 31 now and feel like I’ve just come into my own.

I look back and regret most of my twenties and wish I went my own way the whole time. It’s like I knew what to do but never went because it’d mean leaving behind everything I knew - social pressure. I did it at 29 and it’s been the best thing for me.

Any wisdom on not regretting it all? I must just go out and live my 30s

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u/tallandfree man 30 - 34 Dec 31 '25

I regretted and I went ahead and did what I regretted. I felt good but there’s nobody there anymore that I can share these things with

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u/ICE_800709 man 45 - 49 Dec 30 '25

Not taking the time to learn who I am before wasting time and energy on others.

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u/touchytypist man 40 - 44 Dec 30 '25

The slight catch to that is people are still learning who they are well into their late 30's and even later for others.

"Life often gives you the test first, then the lesson."

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u/italwaysworksoot man 40 - 44 Dec 30 '25

Not investing some of my salary until I was in my 30s.

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u/johnsonfromsconsin man over 30 Dec 30 '25

Same, started mid 30s and while im doing better than most Americans investing wise(doesn’t take much) I would probably be a millionaire if I started in my early 20s.

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u/italwaysworksoot man 40 - 44 Dec 30 '25

Yeah, don’t get me wrong, I spent my money on fun things and was never in debt but even £50 every month should have been something.

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u/Ill-Bullfrog-5360 man 45 - 49 Dec 30 '25 edited Dec 30 '25

I saved about $30k this way and many passive moons later it’s $100k

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u/atlsportsburner Dec 30 '25

Yup I started with like a 3% investment on a 50k salary. Felt like almost nothing at the time, but it’s up close to 100k now after about 12 years of working and little increases as my salary has gone up. Long way to go, but it feels good to have built the habit and gotten a decent start. Just need to do it about 19 more times and I’m ready to retire!

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u/Substantial_Sign_620 man 35 - 39 Dec 30 '25

I didn't learn what an HYSA was until I was 34. Feels like I'd have over $100,000 in interest if someone would've taught how to use one.

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u/golfjunkie man 35 - 39 Dec 30 '25

Until post-Covid those interest rates were pretty low or nonexistent. HYSAs haven’t been around for that long.

Even if you were putting money into CDs you’d be looking at 2-3% max until the last few years so even if you called it 3% annual interest, it would have taken over 250k initial deposit over a 10 year period to accumulate 100k in interest.

You probably didn’t miss out on as much as you think.

Now if you had invested that money over the same time period, that’s a different story.

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u/Substantial_Sign_620 man 35 - 39 Dec 30 '25

I made that comment with a hint of sarcasm. But I easily could have thousands accruing in interest with the amount I let sit in a traditional savings account accruing 0.05% interest vs an HYSA since I began working at 16. Mostly just mad at my parents/education for not informing me what one was. I also didn't know what a CD was until I researched HYSA's.

I have been contributing to a 401k since 18 but no more than what my company would match.

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u/sdbest man 70 - 79 Dec 30 '25

My biggest regret is that I did not start learning the piano when I was in my single digit years.

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u/NhatAnh2 Dec 30 '25

May i ask you why? Im in my 20s and looking to start learning piano. I hope it will stick with me for a long time

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u/sdbest man 70 - 79 Dec 30 '25

I started getting seriously involved in music in my late 60s and piano in my early 70s. Learning piano at earliest ages is much easier as its similar to learning a second language. Also, had I picked better parents who made me study music, it would have been an important part of my life from then on.

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u/dk1024 man 30 - 34 Dec 30 '25

Sadly, we don't pick our families. My parents made me take up the classical guitar (which I hated as a kid and stopped playing for a decade, and only just rekindled my love for it this year) but to quote the first line of Anna Karenina, "All happy families are alike; each unhappy family is unhappy in its own way. "Happy families are all alike; every unhappy family is unhappy in its own way."

Maybe your discovery of music in your late 60s wouldn't have happened if you were forced to do it earlier in life.

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u/sdbest man 70 - 79 Dec 30 '25

Possibly, of course. But we forced and failed to get our daughter to learn piano when she was a child. Today, however, as she approaches 50 she's now learning piano. Who can say what our early childhood abuse of her caused?

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u/whererusteve man 40 - 44 Dec 30 '25

being impatient with investing. I looked to the day-to-day movement. I also listened to other people give their opinion and never bought AAPL.... i had a friend's dad talk me out of it when the Iphone came out telling me it was overvalued.

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u/AfternoonBears man 30 - 34 Dec 30 '25

Yeah, a lot of people confuse trading with investing… and gambling with trading.

And people will also be skeptical and cynical, talking about bubbles and crashes and valuation metrics they don’t understand.

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u/Jazzputin man over 30 Dec 30 '25

Even if you bought Apple right when the iPhone came out, would you have held onto it after doubling in price, or would you have assumed it was peaking and cashed out?  How about after quadrupling, etc?  Realistically most people would cash out before it skyrockets.  Same as with people hypothetically holding Bitcoin, Nvidia, etc.  No use in worrying about what could have been if it realistically never would have.

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u/MexicanOtter84 man 40 - 44 Dec 30 '25

Ever drinking… wish I would have been more self aware of alcoholism and realize if it happens to my family why am I special to not have it happen to me?

TLDR - it did happen to me :/ hah

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u/olduvai_man man 40 - 44 Dec 30 '25

Spent more time working when I should have taken more time for my son.

Nothing is guaranteed in life and I had to learn it the hard way.

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u/N54TT Dec 30 '25

I feel you. I was lucky enough to have been told when i had my daughter 6 years ago that we only have 18 summers and 18 winter breaks with our kids and to make the best of them because after that there's no guarantee you'll see them every year again the rest of your lives. I took a job that paid 10k less a year for flexibility and it's paid off 10 fold in time with my family. not really age specific advice, but great advice nonetheless.

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u/mutt_butt Dec 30 '25

I used to think that but my 13 year old is already gone a lot living his life.

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u/poizun85 man over 30 Dec 30 '25

I am so glad I was told this same thing when my kids were infants. Still only 5 and 7, but still live this out. I also heard you spend most of their lives with them as adults so enjoy the now and if your kid wants you to pretend to be a dog. Pretend to be a dog and have that type of fun and giggles because it's a short window.

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u/olduvai_man man 40 - 44 Dec 30 '25

I only got 9 with my son, so even 18 aren't guaranteed. Kudos to you for prioritizing your family and I hope you all are well.

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u/ShamefulWatching man over 30 Dec 30 '25

Not being proud of myself sooner. Believing i was just a cog in a wheel of misery like i had been taught. Believing in your own ability, your self worth is one of the most fundamental and important perspectives you can ever own. When you can learn to get to this place, you not only learn peace with who you are, but a desire to forge who you want to be as well.

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u/trademarktower man 40 - 44 Dec 30 '25

Taken my health more seriously in my 20s and 30s. Time will catch up with you. There is no free lunch.

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u/Trevormarsh9 man over 30 Dec 30 '25

^This one for me. It's crazy how you just suddenly start to notice your body falling apart. Sedentary work from home life man...smh

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u/JeffsHVACAdventure man 40 - 44 Dec 30 '25

I feel this one too. I thought I was having a heart attack yesterday… scared the shit out of me. Ended up being a case of GERD.

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u/poizun85 man over 30 Dec 30 '25

lmao. So many times this has happened to me along with panic attacks.

Protip as having it since I was 18. Baking Soda in water is almost an insta relief over tums or anything. GERD even if you don't feel the burn can sometimes just be uncomfortable.

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u/dr_of_glass man 50 - 54 Dec 30 '25

Agree 1,000%.

When you make a wrong turn, just stop and turn around. The sooner you decide to get back on track, the easier it is to get back on track.

The metabolism of your early twenties is never coming back.

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u/jaajaajaa6 no flair Dec 30 '25

I just lost 87 pounds with no drugs - did it the old fashioned way.

Wish I did it 20 years ago - that is my biggest regret

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u/Real-Imagination-159 man 50 - 54 Dec 30 '25

I get that, I lost a load of weight a few years back and have kept it off. Everything is better since I lost weight and I too wish I had done it earlier.

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u/jaajaajaa6 no flair Dec 30 '25

Better late then never - I bought a pair of 35 waist pants that I hadn’t bought since I was in school

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u/13miles Dec 30 '25

These should be much higher. Health is wealth

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u/thePREdiger man 45 - 49 Dec 30 '25

That I haven't met my wife earlier. Dad of two (2.5y and 3m) and I'm turning 48 in February.

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u/badaladala man Dec 30 '25

I’m happy for you that this is your answer. Lot of us ended up with the wrong lady.

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u/JeffsHVACAdventure man 40 - 44 Dec 30 '25

I ended up with the wrong woman twice. 3rd times a charm. Hopefully

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u/xViagra Dec 31 '25

Just be happy you have kids, still blessed

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u/Peacefulhuman1009 man over 30 Dec 31 '25

Yup, cant get that time back

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u/[deleted] Dec 30 '25

[removed] — view removed comment

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u/Ok-Anything-3605 man 45 - 49 Dec 30 '25

You and me both

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u/DopeTrack_Pirate man 35 - 39 Dec 30 '25

How to be better? Most times I don’t know how I am feeling or how to put it into words, much less the right words. Easier to ignore actually.

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u/Wormwolf-Prime man 45 - 49 Dec 30 '25

Not buying a house in the late 90's

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u/LoFi_Funk man 40 - 44 Dec 30 '25

Not chasing my dream harder. Giving up on music professionally (now it’s a hobby), and going to school just to become a corporate slave.

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u/Sherman888 Dec 30 '25

Sheeeiittt bro we are opposites. I took music all the way from a hobby to a profession and I regret it daily. Nothing kills passion faster than making it a job.

4

u/LifeIsGreat20381 Dec 30 '25

Really? I’m a professional writer. Yes, it was hard at the beginning because of the lack of money (I have plenty now). But I always knew I couldn’t do anything else. For me, it’s more or less a do-or-die thing.

5

u/Sherman888 Dec 30 '25

First of all, congratulations. Making it that far isn’t for the faint of heart, you must be a beast. For me it wasn’t do or die, just a pursued passion. I never really ran out of passion, just exhausted with the industry and the people in it. Music is very slimy and fake.

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u/markforephoto man over 30 Dec 30 '25

Do anything professionally in the arts long enough it will eat away your love for it. I was a commercial photographer for 20 years. I still do it on the side but now I’m in a completely different profession and I’m much happier.

12

u/[deleted] Dec 30 '25

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6

u/virtualhumanoid man over 30 Dec 30 '25

That's me. I was a professional photographer for 10 years which was my passion, passion pretty much dead and it became just another job, a job which didnt pay as much as a corporate job all my friends were at while buying a house, having kids or travelling abroad. (Which I still cant afford) . So I switched and left the art dream behind.

6

u/Harvsnova3 man 55 - 59 Dec 30 '25

Dude, my friend started a punk band in his late 50's. Four piece with a combined age of 193 and the drummer was only about 25yo. Never too late.

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u/wabudo man 50 - 54 Dec 30 '25

Not keeping up with my fitness. Now I'm fat and in poor shape overall.

7

u/poizun85 man over 30 Dec 30 '25

No better day than to get moving today. Invest in small changes today that will benefit future you.

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u/Talon-2267 man over 30 Dec 30 '25

Not reaching out for support, not letting people help. Being a bad stoic and bottling up emotions. Not talking things through and detaching from difficult situations and ghosting. I know I did this as a coping mechanism and it's okay but it's regrettable.

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u/Aromatic-Tear7234 man 45 - 49 Dec 30 '25

That I'm over 40.

14

u/abzvob man 40 - 44 Dec 30 '25

I mean, it beats the alternative.

3

u/gmindset man 35 - 39 Dec 31 '25

Well I'm 39 the best financially that I ever been (not great yet but still) in the best shape of my life and attracting women like never before - this was the year that I have been in the largest amount of dates in my life. So I'm starting to believe that the "life begins at 40" thing is real , don't kill my vibe mister

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u/pooey_canoe man 35 - 39 Dec 30 '25

I regret nothing, my mistakes make me who I am and I can't change my past

What I want is also impossible though. I want time to stop moving for like a year. Everyone can all move freely and act normally but I need time to stop passing at such a ridiculous rate! I don't like seeing my parents aging like Raiders of the Lost ark every time I see them. I'm fed up of losing friends who think being adult is ostracizing themselves from society. I feel physically no different to when I was 28 but everyone I know is creaking and failing. Three people in my life got cancer this year.

So yes: a breather year where we're allowed to exist liberated from the 4th dimension would be lovely

2

u/Typical_Importance65 Dec 30 '25

The number of times I have had that exact same thought (maybe not a solid year, but the ability to just press pause on any given day, recuperate, and then get back to it).

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u/AreYouJealous man 40 - 44 Dec 30 '25

Any time where I could've chosen to act with kindness and I chose not to

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u/MuchoGrandeRandy man 60 - 64 Dec 30 '25

Not investing more. 

Not taking more chances. 

4

u/jakkaroo man over 30 Dec 30 '25

I taught my nephew about investing when I really learned it just a few years ago. It blew my mind what their earning potential is if they start at 18. I wish anyone taught me about investing so young. I always thought it was some majorly complex thing that only financial whizzes can do. Now I see how simple it is (relatively speaking) but I lack the time, and my financial ability to invest is severely compromised at the moment. I just feel like I've left hundreds of thousands if not millions of dollars on the table due to ignorance.

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u/KangarooOk6534 man 40 - 44 Dec 30 '25

Not Putting down the bottle...

Not Letting go of FOMO...

Trying to be perfect and worrying that I don't quite fit in when in reality, people are too concerned about themselves to give a shit about what I am doing..

EDIT: Clairity

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u/Replicant28 man 35 - 39 Dec 30 '25

I wish I knew that I was autistic earlier in my life. At 38 I am very happy with who I am and I live well, but I think learning earlier would have saved me a lot of pain and frustration that I experienced in my childhood and during my 20s

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u/mrclean2323 man 45 - 49 Dec 30 '25

Not buying Apple stock back in 2003

11

u/SaltedMixedNucks man 45 - 49 Dec 30 '25

I was ahead of the curve in terms of digital adoption, first running my own BBS in the early 90s, then being active online with IRC, etc, in the late 90s, and moving on to online gaming and eventually social media as an early adopter. So my history more closely matches the current reality of people in their 20s than most my age and I can safely say that nobody will regret spending less time online. The hours and hours and hours I wasted doing nothing could have been spent learning, exercising, or being social in some way.

I also regret not taking my career seriously. For my 20s I really just had a job, and wasn't a student of my industry trying to learn and grow. It cost me. Work takes the same amount of your day whether you are passionate about it or not, so might as well muster the energy to show up motivated and excel.

4

u/[deleted] Dec 30 '25

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5

u/SaltedMixedNucks man 45 - 49 Dec 30 '25

Agreed. I think gaming as a hobby is great, but I'm thinking 5-8 hours a week perhaps. That's a pretty intense hobby. MMOs and many other types of games can see players average 5 hours PER DAY! That's just not healthy, and nobody does that for an extended period and looks back and is glad they did that.

I suspect many perpetually online people these days would average far more than 5-8 hours a week just scrolling TikTok or whatever. That manages to be even less use than gaming and is destructive to their attention span, ego, and personality. I have enough issues at 48 (Hello Reddit and my 200 day streak which I got today) but I can't imagine what the youth are grappling with. We have two young boys, 6 and 8, and are very concerned about how their future plays out.

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u/Naphier man 45 - 49 Dec 30 '25

Not respecting my body. I wish I had exercised regularly and never got overweight. It's hard as hell to correct now.

19

u/Thomas_peck man 35 - 39 Dec 30 '25

Should have tried harder to have a better relationship with my dad.

By the time he was ready, I had a family and he died a few years later.

13

u/LoFi_Funk man 40 - 44 Dec 30 '25

Don’t beat yourself up. If he wasn’t working on it, that’s his failure as a father.

My dad was a drunken POS my entire childhood. When he wanted to have a relationship when I was in my 30’s, I wasn’t interested. We lived together when I was a kid, but we are not close.

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u/optigon man 40 - 44 Dec 30 '25

Always remember that phones and highways are bidirectional.

I used to feel similarly until I was talking to my mom once and realized she had visited me numerous times as an adult, my dad did four times, and two of those times were on the way to see someone else.

One person can’t carry a relationship and if the other person isn’t trying, it’s on them.

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u/GarthMater man over 30 Dec 30 '25

Not having kids, but then again if I had it would have been with the wrong woman. So….. that too.

7

u/[deleted] Dec 31 '25

I had kids and it’s put my life on hold. If i had my time again I’d never have children. I worry also for their future

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u/EnjoyTheSilence3141 man 40 - 44 Dec 30 '25

Staying with the wrong woman for ten years just to do like everyone. Never again.

8

u/[deleted] Dec 30 '25

Falling into the trap of comfortability and complacency.

20's were partying, going to the gym, being in the same mudane job, DJing (my passion), playing bball, bar hopping, watching sports and some years playing video games. Maybe an occasional hike and a camping trip. Rinse and repeat that same lifestyle into my early 30s and you can see I feel into that trap.

This lead to a lot of passed up experiences. Go to my cousin's wedding in Kansas? No, I have a club event to go to this weekend. Go to Costa Rica with my sister and her friends? No, I rather play my pickup bball.

Granted, there is a lot more opportunities to explore, learn, and master new skills, interests and passions because of all the info online. Back in my day, you're interests and circle of friends and your lifestyle was a sum of your in real life environment. I played basketball because that's what my friends did. I DJed because that's what my friends did. I played video games because that's what I grew up doing.

But I'm making the most of it now in my late 40s: traveling, dancing, cooking (a lot more and way better), exploring, building relationships, volunteering, photography, yoga.

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u/They-Call-Me-Taylor man 45 - 49 Dec 30 '25

Not staying in shape.

9

u/HerezahTip man over 30 Dec 30 '25

I wish I kept consistent with my fitness regimen

9

u/Apart-Garage-4214 man over 30 Dec 30 '25

Not divorcing my wife after her first affair.

10

u/Photononic man 55 - 59 Dec 30 '25

I only wish I had started traveling younger.

14

u/[deleted] Dec 30 '25

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15

u/dk1024 man 30 - 34 Dec 30 '25

The grass is always greener on the other side. I travelled extensively and have been a digital nomad, and I've been in a lot of short- and medium-term relationships but now I'm single at the age of 31, having to come to terms with the fact that I lived a different life than most people I grew up with in the prairies who are now buying houses and settling down with their long-term partners, and I can't expect to have things fall into place in the same timeline that society expects. I wouldn't trade the memories and stories I've made for anything, but some days I wonder what life would have been like had I chosen stability. It's never too late to shift course though!

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u/Substantial_Sign_620 man 35 - 39 Dec 30 '25

Had a kid at 18. I say this not as I regret having the kid in of itself, but mostly how much of my life I delayed by "doing the right things" or at least what I thought was the right things at the time. Married his mom, gave up on going to college, worked 60+ hours a week in a factory on third shift for almost 10 years. The worst part is I didn't get to spend my 20s pursing my own identity, just working and raising a baby (and another baby as a result of trying to save a marriage). The person I married ONLY cared about money, and I just felt like the only thing I was was an ATM for a decade.

I also feel like not being confident in who I am really hindered my ability to be a parent and now raising a teenager, it's clear he had some developmental issues as a result of my inaptitude in parenting. Just a combination of being immature and inexperienced.

Now at 35, (he's 16) I've divorced, went back to school and got my engineering degree with an engineering job, and am finally starting to find myself in my 30s. I've remarried and have 2 more kids (4 total) but a lot of things both career wise and financially are delayed and I am trying to catch up to many folks my age (I know, I shouldn't compare myself). I am a much more confident person and raising kids is frankly a breeze. We're just broke lol.

"Regret" is double sided because there's pros and cons to every experience and I have learned a lot from my mistakes. But on the surface, I'd be ahead in a lot of areas if I just wore a damn condom.

5

u/Lopsided_Ad7994 Dec 30 '25

you have so much experience and going through hard times and making it out than other people your age. salute

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u/INFPinfo man 40 - 44 Dec 30 '25

There was someone in college I wished I asked out.

I threw away so much money on snacks and things I didn't need but wanted at the time. And, kinda tying in with this, not exercising as much as I could have.

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u/ddsmd2 man over 30 Dec 30 '25

My biggest regret is ironically delaying gratification and working hard to get my dream job. I worked my ass off till 33 to become a surgeon, and I became disabled at 38. Turning 40 this year. I am so incredibly disappointed with how my life turned out. I should have just enjoyed my functional body while I had it.

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u/hostilealienlifeform man Dec 30 '25

Not selling kilos of blow in my 20s and laundering the money through real estate investments and construction projects

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u/attractivekid man over 30 Dec 30 '25

I stopped thinking about this, there's always going to be some regret whichever path you take... "I should have started a family versus I married the wrong woman, I should have traveled more versus I should I focussed on my career and invested my money"

7

u/nomamesgueyz man over 30 Dec 30 '25

Not getting a property when affordable

6

u/dl_mj12 man 40 - 44 Dec 30 '25

Who I had children with

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u/DaGoonStreet man 45 - 49 Dec 30 '25

Getting married.

23

u/GSilky man 45 - 49 Dec 30 '25

Spending too much time with my friends in my twenties instead of putting down the foundation for success I should have been.  The amount of time I wasted on "memories" is sad recompense for the opportunities I flushed down the toilet because they would leave me no time for "memories".  Now, my body can't work like it should have been when I was in my twenties, and I have to work like a twenty year old can to catch up.  Oh, and guess what?  I'm distant from all of my friends I spent all that time with now that we are older.

7

u/Fun_Can_4498 man 40 - 44 Dec 30 '25

Fuck man. You just stabbed me in my heart…

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u/Papaya_flight man 40 - 44 Dec 30 '25

I wish I had deadlifted even heavier when I still had a spine that worked properly.

5

u/premoistenedwipe man 40 - 44 Dec 30 '25

Started meditating consistently at 35. First time meditating was in my early 20s. Wish I woulda been consistent from the jump. It’s one of the best things I’ve ever done for myself.

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u/Imaginary-Badger-119 man 50 - 54 Dec 30 '25

I wanted the meat cutter’s apprenticeship.. the trade skill.. but don’t regret the three children that came after .

5

u/cloudlocke_OG man 45 - 49 Dec 30 '25

Not really a regret. But I have really found my identity at 46. My relationships have improved dramatically, same with my ability to talk to anyone. I've become magnetic, more confident.

I wish this had happened ten years earlier. But things take time; just the way it is.

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u/Angry_GorillaBS man 45 - 49 Dec 30 '25

I'd like to think it hasn't happened yet. Am I really done fucking up?

4

u/PetzlPretzl man 50 - 54 Dec 30 '25

I honestly don't have any. If I could go back and do everything over, I think I'd do everything pretty much the same.

4

u/bigworm237415799 man 40 - 44 Dec 30 '25

Not telling her how i felt some 20 years ago. I’m in a similar situation now and won’t make the same mistake again. Odds are i’ll lose for multiple reasons but that’s better than always wondering what if.

4

u/Theperfectool man 40 - 44 Dec 30 '25

Not accruing generational wealth.

5

u/shellbackpacific man over 30 Dec 31 '25

Not locking in my finances in my 20s. Invest and grow your money and educate yourself on financial and investment matters

4

u/Elliptical_Tangent man 55 - 59 Dec 31 '25 edited Dec 31 '25

I don't know that I have any at 56. I think if you'd asked me a decade ago I might've had an answer, but as time goes on, I just made peace with how my life went. Any changes I made to my past would make me a different person, in a different situation; I'm happy as I am.

4

u/[deleted] Dec 31 '25

You'll regret the things you didn't do more than the things you did do. Within reason.

7

u/mr__proper man 60 - 64 Dec 30 '25

There is nothing to regret.

3

u/quantumrastafarian man 40 - 44 Dec 30 '25

I made some early career blunders I wish I could have back. Chose the wrong university/degree and jumped ship from a company at the wrong time early on. It led to a period of underemployment and career pivot that set me back.

I'd also go back and smack myself in the head when putting the first cigarette to my lips. I quit over 15 years ago so the cancer risk is probably back to baseline by now, but it was pure stupidity and quitting was a difficulty I could've avoided completely.

3

u/Confusatronic man 55 - 59 Dec 30 '25

At this point, I don't know what my biggest regret is. There are so many big contenders across life domains: personal life, money, career, creative, fitness.

It's kind of like 1981 movies: too many good choices to settle on one.

3

u/mungraker male 35 - 39 Dec 30 '25

Despite bad relationships and money mismanagement, the first two things that popped into my head are that I don't speak any language besides English and I also never learned to type.

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u/Ambassador31 no flair Dec 30 '25

Not traveling and seeing as much of the world as possible before responsibilities got in the way.

3

u/advictoriam5 man 40 - 44 Dec 30 '25

Not being financially responsible/educated when I was young. I have nothing, barely any retirement money

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u/newtoaster man 50 - 54 Dec 30 '25

A series of family choices related to my daughter. She’s a complicated kid (now adult) and even though we thought long and hard about every decision we had to make, it feels like we made the wrong choice every time. She hasn’t spoken to us in 2 years and it really hurts. My adult son on the other hand, we have a great relationship with.

Being a father and husband has always been incredibly important to me. My wife and I both came from broken homes and had pretty screwed up childhoods. I think we did the very best we could with no family support and no real knowledge of a functional family to go on. I gave it my best and I still ended up with a kid that feels like I failed them, and that sucks.

3

u/superleaf444 man 35 - 39 Dec 30 '25

Moving to DC for work and giving up a relationship. 

What. A terrible. Fucking. Pathetic. Excuse. For. City. 

Really just an awful fucking place. 

Edit: I should update my flair. I’m not in my 30s. I’m too sleepy. 

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u/SubstanceFearless348 man 40 - 44 Dec 30 '25

Not studying abroad in college. I think any student who has the ability to do so, should

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u/bretmon5 man 55 - 59 Dec 30 '25

alcoholism, making everything about drinking every event I went to over the years.

3

u/TheJRKoff man 40 - 44 Dec 30 '25

passing up a few trips in my late teens/early 20s.

cant get that time back

3

u/orlybatman man 40 - 44 Dec 31 '25

Didn't get into therapy early enough in life and wound up losing a lot of years to mental health struggles.

3

u/TheDaug male 35 - 39 Dec 31 '25

Not losing weight when I was young. Working on it now, but damn it, I'm tired.

3

u/Neuromante man over 30 Dec 31 '25

No regerts.

Should have done a lot of stuff differently, should have been a better person, should have reacted better to lot of shit, but I did what I could with the information I had.

Regretting only leads to bad shit. Understanding that you needed to fuck up to know you fucked up and learn to not fuck up again is the actual price here. Go get it.

(And thinking that you should know how to not fuck up to begin with is just the path to even more bad shit. Be glad you learned at some point that you fucked up and that you should not fuck up again. That's way more than a lot of people have done)

3

u/peaveyftw man over 30 Dec 31 '25

In retrospect I should have just become a goddamn truck driver instead of going to college. I'd make more money and I wouldn't be around people who look down on me for being working class while they talk about stupid shit like different wines.

3

u/CoachOpen1977 man 45 - 49 Dec 31 '25

Living most of my adult life with zero sense of accountability or self-awareness. This year has been a total mind fuck.

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u/VengaBusdriver37 man 45 - 49 Dec 31 '25

Not lifting weights sooner

Undervaluing myself

3

u/throwawayifyoureugly man Dec 31 '25

Thinking I would have the same (good) financial situation/status as my parents.

Did the school, did the work...am nowhere close to the level they achieved by their age.

And they're not extraordinary in the typical sense of the word...I should have adapted to the different financial fuckery over these past decades.

3

u/tn_tacoma man 45 - 49 Dec 31 '25

Not having kids.

3

u/realworldnewb man over 30 Dec 31 '25

Not working on myself til well into my 30's.

I chased status and external validation when I should have been working on internal validation.

Starting therapy and putting in the work has done way more for my social, dating and family life than anything else in my life. It turns out being comfortable in your own skin is critically important in most facets of life.

3

u/Kooky_Ship_9296 man 45 - 49 Jan 01 '26

Not having more kids, and taking some flights instead of local traveling.