10 things men regret the most in their lives — here is what to learn before it’s too late
Reddit users shared their biggest mistakes in life, offering crucial takeaways to keep in mind while you still have time.
Someone dropped a single question into the AskReddit thread: “What is your biggest regret in your entire life?” No context, no framing, just the question.
Thousands of people reacted, and this simple question quickly became one of the hottest topics. The internet is usually full of noise, and it’s hard to filter out what is real and useful from what is just fluff. But this conversation was different. It was something honest, the kind of thing people usually share after knowing each other for a long time.
The thread drew the kind of responses that take a lifetime to accumulate. Marriages gone wrong, fathers who died early, bitcoin left on the table, or jobs that paid well and slowly hollowed people out. The sheer range of it was something, but what stuck was how many of these regrets rhymed across different lives, decades, and continents.
1. Marrying the wrong person
The top comment in the thread was short and blunt: “Marrying the wrong person for sure. Got out of it relatively easily and without children, thank god.”
That word “thank god” carries a lot of weight. The relief in it suggests the person knows exactly how much worse it could have been, and exactly how close they came. Your partner shapes almost every significant decision of your adult life: where you live, how money flows, whether you wake up feeling like yourself or slowly disappearing. The wrong person does not just make you unhappy in a manageable way. They shift the whole trajectory. Who you become over 10 or 20 years is partly a product of who you choose to come home to, day after day.
2. Not pushing him harder to see a doctor
A woman in the thread wrote something that stopped the scroll: “I guess I wish I had badgered him even more forcefully to see the doctor. He should still be here. Men, get your prostate testing done.”
A commenter shared that her father put off persistent pain for too long. By the time he finally saw a doctor, the prostate cancer had spread to stage four. He died at 56, and his grandchildren will only know him through stories.
It wasn’t the only regret connected to doctor visits: “Just men go to the doctor.” She identified herself as a colon cancer widow.
Three separate people, three different cancers. The myth that prostate cancer is slow-moving and manageable has cost lives. One of the commenters pushed back directly: “That ‘die with prostate cancer’ thing is a huge disservice. Many are not indolent, and those kill quite efficiently.” Prostate cancer remains the leading cause of cancer death in men. The only variable that actually changes outcomes is catching it early.
3. Never saving or investing when young
“I just always thought I had the time,” one commenter wrote, reflecting on years of not putting anything away. “You realize as you get older, time moves very fast.”
Another spelled it out in concrete numbers: by starting a child’s investment fund a few years late, that child will have around $25,000 by age 21 instead of over $100,000. Nobody in their twenties feels urgency around this because the consequences are invisible. The money you do not save at 22 does not vanish with a bang. It simply fails to become what it could have been, and you only see the gap decades later, when seeing it clearly no longer helps much.
4. Missing the Bitcoin moment
“Not dropping $25k on Bitcoin and Bitcoin mining in 2013. I knew of it, I had an opportunity. I had the money. I blew it. It all went to dr*gs and raving and living pretty outside my means instead. To be 23 and dumb again.”
That $25,000 in 2013 Bitcoin would be worth more than $75 million today. The number is almost too absurd to hold in your head. But the thread handled this one better than expected. Several people pushed back: even if you had bought in, would you have held through the years of volatility? Almost certainly not. One commenter admitted to mining several hundred Bitcoin and selling nearly all of it for under $10 each, and said they had zero regrets. “It just as easily could have been worth nothing,” they said. The real regret is not missing Bitcoin specifically. It is spending money you had on things that left nothing behind.
5. Playing it safe
“Playing it safe,” one commenter wrote, with nothing else attached.
When someone asked what they meant, the answer opened up. They were not talking about recklessness. They were talking about choosing a stable office job over the kind of life they actually wanted. They mentioned a friend who spent his adult life teaching English in different countries, never making much money, but waking up happy. “I wish I did something like that rather than put up with decades of miserably boring office jobs because they were stable and paid well.”
Safety feels like wisdom at 25. By 55, it can feel like a sentence you handed yourself. The choice between fulfillment and security is not always binary, but it is also not as guaranteed as people tell themselves when they take the safer path.
6. Pulling away to avoid being a burden
“Distancing myself from people cuz I thought I didn’t wanna burden them with my problems,” one commenter wrote.
This one is quiet but cuts deep. Men are statistically more likely to isolate when struggling and less likely to reach out, and this comment captures exactly why: the belief that your problems are “too much” for the people around you. That belief is almost always wrong, and it costs real friendships and real relationships year by year.
Isolation compounds every other problem. It makes hard things harder, and it leaves you alone with a version of events that grows darker the longer you sit with it. The people who care about you want to know what is going on. The ones who would not handle it were never really there.
7. Cheating on my wife
“Cheating on my wife,” one commenter wrote. Four words, no elaboration.
Someone else in the thread offered the same answer immediately. A follow-up question asked whether she was still his wife. The answer, weeks later: they were separated now.
Infidelity ends two things at once: the relationship you already had, and any realistic version of the future you were building inside it. Even when it does not end the marriage on the spot, it rewrites every memory before it and colors every moment after. The person who made that choice and the person who has to live with having made it are the same person, and they carry it for good.
8. Starting smoking and drinking too young
“Starting drinking and smoking at too young of an age,” one commenter wrote. “It ages you. I would never have done it.”
Another framed it from a financial and physical angle: years of paying money to damage their own health, with effects they described as ones they would “truly never fully recover from.” The money was gone. The health damage was permanent.
Smoking in particular is one of those things that reads as a personality at 16 and as a mistake at 40. The same goes for heavy drinking started early. Neither is impossible to walk back from. But neither is free, and the cost accumulates in ways that are difficult to reverse.
9. Not spending more time with his mom
“Even though it’s been over 30 years since she passed, spending more time with my mum,” one commenter wrote. “I miss her every day.”
Thirty years later. Every day. There is not much to analyze here. The people who showed up for you in irreplaceable ways are on a clock you cannot see. The Sunday you skip, the call you push to next week, the visit you reschedule to next month: each one is a small withdrawal from an account with a fixed and unknown balance.
Nobody in a thread like this ever writes that they wish they had spent more time at the office.
10. Not getting mental health help sooner
“Not getting help sooner for depression and anxiety,” one commenter wrote. “I feel a lot of regret for the years of pain and life opportunities I lost because of deep self-hatred. For me, medication was necessary, and I tried to muscle through life for so long without. Everyone is different, but the right medication and a good therapist changed my life.”
This one took courage to write. It reflects something many men recognize but rarely say out loud. Struggling in silence feels like strength until you realize it is just a longer and more damaging path to the same destination.
The idea that therapy is a last resort for people in crisis is exactly backward. Getting help when things are hard keeps people from getting worse. The years this commenter described losing to depression are years they cannot get back. The treatment that eventually changed their life was available earlier. They simply could not reach it yet.
A single question asked on the internet produced thousands of honest answers from real lives. The regrets people carry are remarkably consistent across ages, backgrounds, and circumstances: the wrong partner, the ignored symptoms, the money never saved, the risk never taken, the parent not called enough, the habit started too young, the help asked for too late.
None of these are extraordinary failures. They are ordinary human decisions that accumulated weight over time. Which means you are probably somewhere in the middle of making some version of them right now, and the window to choose differently is still open.
