I never thought I would have to tell a grown man in his mid-thirties to stop living in the past, but here I am. I am 35 years old, and my friend, who is 36, still seems to be emotionally stuck in high school. We have known each other for years, and while I have always appreciated his friendship, his obsession with things that happened nearly two decades ago has become increasingly exhausting. Most people our age are focused on their careers, relationships, families, finances, and future plans. My friend, however, still spends a surprising amount of time talking about people who embarrassed him, rejected him, or supposedly treated him unfairly when we were teenagers. At first, I thought he was simply reminiscing about old times, but eventually, I realized that he genuinely holds grudges against people he has not seen in years.

One of the biggest issues is that he remembers almost every negative interaction he had in high school. He can tell you exactly who made fun of his clothes, who did not invite him to a party, who rejected him romantically, and which classmates he believes thought they were better than him. Some of these incidents happened when we were sixteen or seventeen years old. I understand that teenage experiences can be painful, especially when someone feels excluded or humiliated, and I am not suggesting that his feelings were never valid. However, there is a difference between remembering something unpleasant and allowing it to influence your entire adult life. My friend seems unable to make that distinction, and whenever someone from our past comes up in conversation, he inevitably brings up something negative they did to him.

What makes the situation particularly frustrating is that many of the people he complains about have moved on with their lives. Some are married, some have children, and others have moved to different cities or built successful careers. Most probably do not even remember the incidents he still talks about. Meanwhile, my friend continues to discuss them as though the events happened last week. If someone mentions an old classmate, he immediately starts explaining why that person was a terrible human being or why they never deserved the success they achieved. Sometimes, he even looks up their social media profiles and makes comments about their lives. I have tried changing the subject, but he usually finds a way to return to the same complaints.

For a long time, I tried to be understanding because I knew my friend had experienced some difficult moments during his teenage years. He was not particularly popular in school, and there were people who made jokes at his expense. He also had a few romantic disappointments that clearly affected his confidence. I listened to him when he needed to talk, and I never told him that his experiences were meaningless. Everyone deals with rejection and embarrassment differently, and I understand that certain memories can stay with someone for a long time. However, I eventually began to feel that our conversations were becoming repetitive and unhealthy. Instead of discussing how he could improve his life now, he kept focusing on people who had hurt his feelings twenty years ago.

The breaking point came recently when a mutual acquaintance mentioned that one of our former classmates had recently received a promotion at work. Instead of simply congratulating him or moving on with the conversation, my friend immediately began criticizing the man. He claimed that the former classmate had always been arrogant and did not deserve his success because he used to make jokes about other students in high school. He then spent nearly half an hour explaining why he believed this person had never changed and why people like him always managed to get ahead in life. I finally interrupted him and asked why he still cared so much about someone he had not spoken to in almost twenty years. He became defensive and said that I would understand if I had been treated the way he was treated.

I told him that I did understand that he had been hurt, but I also believed that he needed to stop allowing those experiences to control his present life. I reminded him that he was thirty-six years old, not sixteen, and that he could not keep blaming people from high school for his current frustrations. I told him that those people were not responsible for every disappointment he experienced as an adult, and that constantly comparing himself to them was only making him miserable. I also said that if he wanted to build a happier life, he needed to focus on what he could change rather than spending so much time being angry about things he could no longer control. I was more direct than I usually am, but I felt that someone needed to tell him the truth.

My friend did not take my comments well at all. He accused me of being insensitive and said that I was minimizing everything he had gone through. According to him, I had no right to tell him how he should feel about his past, especially because I had not experienced exactly what he experienced. He also claimed that I was defending the people who had bullied him and that my comments proved I did not understand what real friendship meant. I tried to explain that I was not defending anyone who had mistreated him. I was simply saying that he deserved to enjoy his life without constantly carrying resentment toward people who might not even remember what happened. Unfortunately, he was too angry to listen, and our conversation ended badly.

Since that argument, things have been awkward between us. He has barely spoken to me, and I recently heard from another mutual friend that he has been telling people I am judgmental and dismissive of his feelings. A few people have suggested that I should apologize because I was unnecessarily harsh and that old wounds do not disappear simply because someone reaches a certain age. I understand their point, and I have started wondering whether I could have expressed myself more gently. Perhaps I should have asked him more questions about why those memories still affected him rather than telling him directly to get over them. At the same time, I feel that I have listened to the same complaints for years without seeing him make any effort to move forward.

I do care about my friend, and I do not want our friendship to end over this disagreement. I am not expecting him to forget every unpleasant thing that happened during his teenage years, nor do I believe that reaching adulthood automatically makes painful experiences disappear. However, I think there comes a point when a person has to decide whether they want to keep reliving old disappointments or start focusing on the life they have now. I told him he was thirty-six and needed to get over high school because I was tired of watching him remain angry about events that happened almost twenty years ago. Now I am wondering whether my honesty crossed a line. AITA for telling my friend that he is thirty-six years old and needs to get over high school?

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AITA for telling my friend he’s 36 and needs to get over high school?

My friend and I are both 36-year-old men, and I have reached the point where I genuinely cannot stand listening to him talk about high school anymore. I have known him for a long time, and while we have had plenty of good memories together, there is one thing about him that has become increasingly frustrating over the years.

He seems completely unable to move on from his teenage years. Every time we hang out, he somehow finds a way to bring the conversation back to how popular he was in school, how many people knew him, how much attention he received, and how other guys supposedly wanted to be him.

At first, I thought he was just joking around or enjoying a little nostalgia, but after hearing the same stories hundreds of times, I have started wondering whether he genuinely believes his high school years were the most important period of his life.

Whenever we meet up, it does not take long before he starts talking about the old days. We could be discussing work, relationships, weekend plans, or something completely unrelated, and somehow he will find an opportunity to mention his popularity in high school. He constantly talks about the parties he attended, the people he knew, and how everyone supposedly respected him. According to him, he was one of the most recognizable guys in our school, and people would always notice when he walked into a room.

He tells these stories with such confidence that someone who had never met him before might think he was describing a successful career or some major achievement rather than ordinary teenage experiences from nearly twenty years ago.

The thing that makes it especially irritating is that he does not simply reminisce about funny memories or share stories that everyone can enjoy. Instead, he treats his teenage popularity like an accomplishment that still deserves recognition today. Whenever an old classmate comes up in conversation, he immediately starts explaining where that person stood socially compared with him. If someone mentions that a former classmate is doing well professionally, he sometimes makes comments about how that person was never as popular as he was.

He seems to believe that whatever social ranking existed in high school is still relevant, even though we are now adults with jobs, responsibilities, bills, and entirely different lives. I honestly do not understand why he still cares so much about something that happened when we were teenagers.

His stories about dating are even worse. Whenever we are driving somewhere and happen to pass a group of teenage girls, he almost always makes some comment about how he used to attract the hottest girls in school. He will start talking about a particular girl he dated or claim that every guy in our year was jealous because he managed to get her attention. Sometimes, he describes himself as if he were some kind of legendary heartbreaker who could have dated practically anyone he wanted. He tells these stories as though they prove something about who he is today, and he seems to expect me to be impressed every time he repeats them. The fact that we are both 36 makes the whole thing feel even more ridiculous.

We are not teenagers trying to establish who was the coolest guy in school anymore, yet he keeps behaving as if that competition never ended.

I have tried to ignore it for a long time because I do not want every conversation to turn into an argument. When he starts telling one of his usual stories, I normally nod, laugh politely, or try to change the subject. Sometimes I will mention something happening in my own life to redirect the conversation, but he usually manages to bring it back to himself. If I talk about work, he will explain how popular he was with teachers and classmates. If we discuss relationships, he will bring up his high school dating history. Even when we are talking about something as simple as going out for dinner, he somehow finds a reason to mention the parties he used to attend and the people who supposedly admired him. It feels as though he cannot enjoy the present without constantly reminding everyone about the person he believes he was twenty years ago.

What bothers me most is that I do not think he realizes how he comes across to other people. When we are around mutual friends, he often tells the same stories, sometimes repeating details that everyone has already heard many times. People usually respond with polite smiles or brief laughs, but I have noticed that some of them become quiet or try to change the subject. Nobody seems particularly interested in hearing another story about how he was supposedly the most popular guy in school. However, he interprets their reactions as proof that they are impressed by him. He seems convinced that everyone still wants to hear about his teenage glory days, even when it is obvious that the conversation has moved on.

Last weekend, we were hanging out together, and the same thing happened again. We were driving around, talking about our plans for the coming week, when we passed a group of teenage girls walking along the sidewalk. Almost immediately, he started talking about how he used to be able to attract the hottest girls in school.

He mentioned an ex-girlfriend from our teenage years and went into another long explanation about how all the other guys were jealous of him because he had managed to date her. He even started talking about how he could have had almost any girl he wanted back then.

I had heard variations of this story so many times that I could practically predict what he would say next. I just sat there wondering why a 36-year-old man was still so concerned with proving that teenage boys had once envied his dating life.

I finally lost my patience and told him that he needed to grow up. I said that we were both 36 years old, that nobody really cared who had been popular in high school, and that he needed to stop acting as though he were still living there. I explained that there was nothing wrong with remembering the past, but constantly bragging about teenage popularity was getting embarrassing. We had both grown older, and our lives should be about what we were doing now rather than about who we had been when we were sixteen.

I was not trying to start a huge fight, but I was tired of pretending that his stories were interesting when they had become repetitive and uncomfortable to listen to.

He immediately became defensive. Instead of considering what I had said, he accused me of being jealous because I supposedly had not been as popular as him in high school. He said that I was only criticizing him because I could not relate to the attention he received back then. According to him, I was bitter because he had been more successful socially, and I was trying to bring him down because I could not accept that he had been the better-looking or more desirable guy.

I honestly could not believe that he had responded that way. The fact that he immediately turned the conversation into a competition about our teenage popularity seemed to prove my point more clearly than anything I could have said.

I told him that I was not jealous of anything he had done in high school. I genuinely could not care less about who had been popular, who attended the most parties, or who dated the most attractive person when we were teenagers. Those things might have seemed important at the time, but they do not determine someone’s value as an adult. I told him that if he was still trying to prove that he was the coolest guy in the room at 36, then perhaps high school had been the peak of his life. I admitted that it was a harsh thing to say, but I was frustrated by his constant need to bring up the same stories and compare himself with people he had not seen in years.

That comment made him even angrier. He told me that I had crossed a line and that there was nothing wrong with being proud of his past. I agreed that there was nothing wrong with having good memories or being proud of things that happened earlier in life. The problem was that he seemed incapable of discussing almost anything without turning it into a story about how impressive he had supposedly been as a teenager. I tried explaining that I was not asking him to forget his past.

I was asking him to stop treating it as though it were an achievement that everyone else needed to admire.

There is a difference between enjoying old memories and constantly demanding recognition for something that happened nearly two decades ago.

The conversation ended badly, and we have barely spoken since. He has been distant whenever I have tried to contact him, and I get the impression that he is still angry about what I said. Part of me feels guilty because I know that friendships can survive disagreements more easily when people speak respectfully. Perhaps I could have explained my frustration without telling him that high school might have been the peak of his life. That was probably the most hurtful part of what I said, and I can understand why it upset him. However, another part of me feels relieved that I finally said something after years of listening to the same stories.

I have also started wondering why he is so attached to his teenage identity in the first place. Maybe he feels that his adult life has not turned out the way he expected, and remembering high school gives him a sense of importance. Perhaps he misses the attention he received when he was younger, or maybe he simply enjoys telling stories about a time when he felt confident and admired. I do not know what is going on in his head, and I do not want to assume that his behavior means he has failed in life. Everyone has different experiences, and there is nothing inherently wrong with looking back fondly on one’s younger years. Still, if he is unhappy with his present life, constantly talking about high school does not seem like a particularly healthy way to deal with it.

I also recognize that I could have handled the situation more tactfully. Instead of letting my frustration build up until I snapped, I could have told him earlier that the repeated stories were becoming exhausting. I could have asked him why those memories were so important to him or explained that I wanted our conversations to focus more on our current lives.

Maybe he would have reacted differently if I had approached the issue with more patience. On the other hand, I have tried changing the subject and politely moving the conversation along many times, and none of those attempts seemed to make a difference. Eventually, I reached a point where I could no longer pretend that I enjoyed listening to him brag about his teenage popularity.

I have not contacted our other friends to complain about him, and I am not interested in turning this disagreement into a bigger social conflict. I do not want people taking sides, and I am not trying to embarrass him in front of anyone.

He is still my friend, and I would prefer to resolve the issue rather than allow one argument to destroy a friendship that has lasted for years. However, I also do not want to apologize simply for expressing a genuine frustration. If I apologize, I want it to be because I recognize that my wording was unnecessarily harsh, not because I believe I was wrong to ask him to stop constantly reliving high school.

At the end of the day, I think people should be able to enjoy memories from their younger years without being judged. I have plenty of memories from high school myself, and occasionally my friends and I talk about funny things that happened back then. The difference is that those conversations are usually brief, enjoyable, and shared by everyone. We laugh about the past and then move on to whatever is happening in our lives today. My friend seems unable to do that.

He repeatedly returns to the same stories and uses them to establish that he was once more popular, more desirable, and more important than the people around him. I am tired of feeling as though every casual conversation has to become a competition that ended almost twenty years ago.

So, Reddit, am I the asshole for telling my 36-year-old friend to grow up and stop acting as though he is still in high school?

I understand that I was blunt and that telling him high school might have been the peak of his life was a particularly harsh thing to say. However, I am genuinely exhausted by his constant bragging about teenage popularity and dating experiences.

I want to enjoy spending time with my friend without hearing the same stories over and over again. Was I wrong to finally tell him how I felt, or was it reasonable to point out that he needs to focus on his life today rather than constantly trying to prove how impressive he was as a teenager?

My 36-Year-Old Friend Still Holds Grudges From High School

I never imagined that I would have to tell a grown man in his mid-thirties to stop acting like he was still in high school, but here I am. I am 36 years old, and my friend, who is also 36, seems completely unable to move on from things that happened when we were teenagers. We have known each other for years, and although I have always valued our friendship, his obsession with his high school days has become increasingly exhausting. Most people our age are focused on their careers, relationships, families, financial responsibilities, and plans for the future. My friend, however, still spends an unbelievable amount of time talking about people who supposedly embarrassed him, rejected him, or treated him unfairly when we were sixteen or seventeen. At first, I thought he was simply reminiscing about old memories, but I eventually realized that he genuinely holds grudges against people he has not spoken to in nearly twenty years.

Whenever we hang out, it does not take long before he brings up something from high school. We could be discussing work, weekend plans, relationships, or even something as simple as where we should go for dinner, and somehow he finds a way to turn the conversation toward his teenage years. He remembers who was popular, who was unpopular, who attended certain parties, and who supposedly thought they were better than everyone else. He talks about his experiences as though the social hierarchy from our school days still exists and everyone should remember their place in it. Sometimes, I wonder whether he realizes how strange it sounds for a 36-year-old man to remain so invested in teenage popularity contests that ended almost two decades ago.

One of the most frustrating things about his behavior is that he does not simply share funny memories or laugh about the embarrassing things we did when we were younger. Instead, he treats almost every old interaction as evidence of how people behaved toward him. If someone made a joke at his expense in school, he still considers that person a terrible human being. If a classmate did not invite him to a party, he remembers it as a deliberate attempt to humiliate him. If someone who was more popular than him received attention from others, he still talks about how that person was arrogant and undeserving of their reputation. He seems unable to accept that teenagers can be immature, make mistakes, and eventually grow into completely different adults.

I understand that high school can be a difficult time for many people. Teenagers are often insecure, emotional, and overly concerned about what others think of them. Being excluded from a group, getting rejected by someone you like, or becoming the target of jokes can genuinely hurt. I am not suggesting that people should simply forget every unpleasant experience they have ever had. I have my own memories of things I wish had gone differently, and there are certainly moments from my younger years that I would not want to repeat. However, I do not spend every weekend talking about those experiences or allow them to determine how I feel about people today. I have accepted that those years are part of my past, and I believe my friend would benefit from doing the same.

My friend seems particularly obsessed with the people who were considered popular when we were in school. He constantly compares their lives with his own and makes comments about whether they have achieved anything worthwhile since graduation. If someone mentions that a former classmate has a successful career, he immediately brings up something embarrassing that person supposedly did as a teenager. If he learns that someone is happily married, he might joke that the person was never particularly attractive in school. If another former classmate has become financially successful, he sometimes suggests that they were probably always good at pretending to be important. It feels as though he cannot accept that people he disliked in high school might have grown into successful, happy adults.

The strangest part is that most of these former classmates have probably forgotten the incidents he still talks about. They have their own lives, families, responsibilities, and problems to deal with. Some have moved away, while others are busy raising children or building careers. I doubt many of them spend even a few minutes thinking about what happened in high school, let alone spend their adult lives holding grudges over it. Meanwhile, my friend can remember the smallest details of interactions that happened when we were teenagers. He will bring up a person’s name and immediately explain why he never liked them, often describing an incident that happened so long ago that I barely remember it myself.

I have tried to be patient with him because I know that everyone has different experiences growing up. I also know that some people struggle with confidence and may continue to think about situations that made them feel embarrassed or rejected. For years, whenever he complained about someone from school, I listened and tried to understand his perspective. I would occasionally agree that certain people had behaved badly, especially if I remembered the incident myself. I did not want to dismiss his feelings or make him think that I was defending people who had mistreated him. However, over time, I began to notice that listening to him was not helping him move forward. Instead, it seemed to encourage him to revisit the same negative memories again and again.

Our conversations have become increasingly repetitive because he often tells the same stories multiple times. Sometimes, he will describe an incident from high school as though he is telling me about it for the first time, even though I have heard the story dozens of times. If I point out that he has already told me about it, he simply continues explaining why the other person was wrong. He seems to believe that repeating the story somehow proves that he was the victim and that everyone else should recognize how unfairly he was treated. I have reached the point where I can practically predict what he will say before he finishes his first sentence.

Another issue is that he sometimes looks up former classmates on social media and then uses whatever he finds as an opportunity to criticize them. If someone posts pictures of a vacation, he might suggest that they are trying too hard to show off. If someone shares a professional achievement, he might claim that they were always desperate for attention. If someone posts a family picture, he sometimes makes comments about how they used to behave in school and how they do not deserve to appear so happy now. I find this behavior uncomfortable because these people are simply living their lives, and there is no reason for him to interpret every update as a personal insult or an invitation to compare himself with them.

What makes the situation even more confusing is that my friend is not a teenager who has only recently graduated. We are both 36 years old. We have spent almost two decades living as adults, and during that time, we have had plenty of opportunities to build new relationships, learn from our mistakes, and develop different priorities. Yet he still seems to measure people’s worth according to what happened in high school. He talks about popularity as though it were a permanent achievement that should follow someone throughout their life. I honestly cannot understand why he cares so much about something that has very little relevance to the person he is today.

The breaking point came last weekend when we were hanging out together. We had planned to spend a few hours catching up, talking about work, and discussing some plans for the coming weeks. Everything was fine at first, and I was enjoying the conversation. Then he brought up a former classmate who had recently achieved something significant in his career. Instead of acknowledging the achievement or simply moving on, my friend immediately started talking about how that person had acted superior to everyone in high school. He complained about the way the classmate used to speak to people and claimed that his current success was undeserved because he had been arrogant as a teenager.

I tried to steer the conversation in another direction because I did not want to spend another afternoon discussing the same old grievances. I mentioned that people often change as they get older and that someone who behaved badly at seventeen might be a completely different person at thirty-six. My friend dismissed that idea almost immediately. He insisted that people rarely change and that the classmate was probably still the same arrogant person underneath his success. He then began listing other people from our school who had supposedly wronged him, turning what had started as a casual conversation into another long discussion about events from nearly twenty years ago.

At that point, I lost my patience. I told him that he needed to get over high school because we were both 36 years old and had more important things to worry about. I explained that I understood he had experienced unpleasant moments when he was younger, but constantly holding grudges against people from that period was not helping him. I told him that he could not keep allowing things that happened when we were teenagers to control his mood and influence how he viewed everyone around him. I also pointed out that many of the people he complained about had probably moved on with their lives and were no longer thinking about those incidents at all.

My friend immediately became defensive. He accused me of being insensitive and said that I had no right to tell him how he should feel about his past. He argued that I did not understand how much certain experiences had affected him and that I was making fun of his feelings instead of supporting him. He also suggested that I was taking the side of the people who had treated him badly, even though I had not defended anyone or claimed that his experiences were unimportant. I was trying to explain that remembering something painful was one thing, but allowing it to dominate your life decades later was another.

I tried to clarify my point, but he was already angry. I told him that I was not asking him to pretend that nothing bad had ever happened to him. I was simply suggesting that he stop giving those people so much control over his present life. I said that if he spent all his time thinking about people who had hurt his feelings in high school, he would never have the opportunity to appreciate the people and experiences he had now. Instead of considering what I was saying, he accused me of acting superior and claimed that I thought I was better than him because I had supposedly moved on more successfully.

That accusation frustrated me even more because the conversation had never been about comparing our lives. I was not trying to prove that I was more mature or successful than he was. I simply wanted to spend time with my friend without hearing another complaint about something that happened when we were sixteen. I told him that I was tired of having every conversation turn into a discussion about who had been popular, who had been mean, and who supposedly deserved to be successful. I reminded him that we were adults and that our lives should be about more than trying to settle imaginary scores with former classmates.

He responded by saying that I would never understand because I had not experienced high school the way he had. According to him, some people had treated him unfairly, and he believed that remembering their behavior was a way of holding them accountable. I told him that holding someone accountable was not the same as spending twenty years resenting them. If someone had genuinely harmed him, he was entitled to acknowledge that experience and decide what boundaries he wanted to maintain. However, constantly bringing up old incidents and criticizing people who were no longer part of his life seemed to be causing him more frustration than it was causing anyone else.

The conversation eventually became so tense that we stopped talking about the issue and went our separate ways. I expected him to calm down after a little time had passed, but he has barely spoken to me since. When I have sent him messages, his responses have been brief, and he has not made any effort to arrange another get-together. I get the impression that he is still offended by what I said, particularly because I told him that he needed to get over high school. Part of me feels bad about how blunt I was, but another part of me feels relieved that I finally expressed something I had been thinking about for years.

A mutual friend recently contacted me and asked what had happened between us. Apparently, my friend had told him that I was being judgmental and dismissive of his experiences. He described our argument as though I had attacked him for having feelings about his past, rather than explaining that I was tired of hearing the same complaints repeatedly. Our mutual friend suggested that I should apologize because everyone has different ways of dealing with painful memories and that I might have been too harsh in telling him to move on. I understand that perspective, and I have started wondering whether I could have expressed myself in a kinder way.

At the same time, I do not think it is unreasonable to expect an adult friendship to involve more than repeatedly revisiting the same negative experiences. I have listened to my friend talk about high school for years, and I have never told him that his feelings were meaningless. I have tried to change the subject, offered different perspectives, and encouraged him to focus on his current life. None of those approaches has made much difference. Eventually, I reached a point where I could no longer pretend that I enjoyed these conversations or that his constant resentment was harmless.

I also wonder whether his attachment to high school comes from something deeper than the incidents themselves. Perhaps he misses the feeling of being younger, when popularity and social status seemed more important. Maybe he feels that his adult life has not turned out the way he expected, so he keeps returning to a period when he felt more confident or important. It is possible that those memories represent a time when he felt accepted or admired, and he is struggling to find that same sense of belonging now. I do not know whether any of that is true, and I do not want to make assumptions about his personal life, but I sometimes wonder whether his constant complaints are covering up disappointment about the present.

If that is the case, I would genuinely like to help him find ways to feel better about his current life. I would be willing to listen if he wanted to talk about something that was still affecting him or discuss what he could do to improve his situation. I do not want him to feel that he has to hide his feelings from his friends. However, there is a difference between talking through a painful experience and repeatedly using it as a reason to dislike people who have moved on. I think he deserves to feel happier than he currently seems, but I also believe that he has to be willing to look at his life today rather than constantly comparing it with his teenage years.

I have not contacted the former classmates he complains about, and I have no intention of getting involved in whatever happened between them. I do not know every detail of his experiences, and I am not interested in deciding who was right or wrong in every incident from our school days. What I do know is that holding grudges for decades seems exhausting. I cannot imagine spending so much time thinking about people I no longer speak to, especially when there are so many other things happening in life that deserve attention. I would rather focus on my relationships, my goals, and the people who are actually present in my life today.

I also realize that my friend may see my comments as a betrayal because he expected me to agree with him. Sometimes, people want their friends to validate their feelings rather than challenge the way they think about a situation. Perhaps he was hoping I would listen, agree that his former classmates were terrible people, and help him feel justified in his resentment. Instead, I told him that I thought he was allowing the past to affect him too much. I can understand why that response might have felt unsupportive, especially if he genuinely believes that the events still matter. However, I do not think friendship requires me to agree with everything someone says, particularly when I believe their behavior is making them unhappy.

Looking back, I probably could have chosen my words more carefully. Telling someone to get over something can sound dismissive, even when the intention is to encourage them to move forward. I could have said that I understood why those memories mattered to him but that I was concerned about how much time he spent focusing on them. I could have explained that I wanted our friendship to be about our present lives and shared experiences rather than old conflicts. That would probably have been a more constructive way to communicate my frustration. Still, I do not think the fact that my wording was imperfect means that my underlying point was wrong.

I am also not expecting him to forget everything that happened in high school or suddenly become a different person overnight. Everyone has memories that affect them, and some experiences can take a long time to process. I simply wish he could recognize that he has more control over his life now than he did when he was a teenager. He can choose who he spends time with, what relationships he maintains, and how much attention he gives to people from his past. He does not have to keep reliving old arguments or measuring his current worth against a popularity contest that ended years ago.

What makes me sad is that our friendship used to feel much easier. We could spend hours talking about different subjects, making jokes, sharing stories, and discussing whatever was happening in our lives. Lately, it feels as though every conversation eventually returns to the same handful of people and the same old grievances. I miss being able to enjoy his company without worrying that something I say will lead to another long discussion about a former classmate who embarrassed him in school. I want our friendship to move forward as we grow older, rather than remaining trapped in the same conversations we were having when we were teenagers.

I am considering reaching out to him and apologizing for the way I expressed myself, while still being honest about why I became frustrated. I do not want to pretend that I regret saying anything at all, because I genuinely believe that his constant resentment is preventing him from enjoying the present. However, I can acknowledge that telling him to get over high school may have made him feel that I did not care about his experiences. I would like to explain that I do care about him, and that my intention was not to embarrass or belittle him. I just want him to understand that I cannot keep having the same conversation every time we meet.

At the same time, I am worried that apologizing will make him believe that his behavior is perfectly reasonable and that I was wrong to challenge it. I do not want to encourage him to continue spending so much time criticizing people from his past. I would prefer that we find a way to talk about the issue honestly and agree to focus more on the lives we are living now. If he wants to discuss something that genuinely still hurts him, I can listen, but I do not want every casual conversation to turn into another list of people he believes wronged him twenty years ago.

Ultimately, I do not think being thirty-six means someone must have completely resolved every difficult experience from their teenage years. People grow at different rates, and there is no specific age at which everyone is expected to stop feeling hurt by the past. However, I believe that adulthood also involves recognizing when an old grievance is no longer helping you and deciding whether it is worth continuing to carry it. My friend seems to have built a significant part of his identity around things that happened in high school, and I worry that he is missing opportunities to enjoy the person he could become today.

So, Reddit, AITA for telling my 36-year-old friend that he needs to get over high school and stop holding grudges against people from nearly twenty years ago? I know I was blunt, and I can admit that my choice of words was harsh. However, I have listened to the same complaints for years, and I am exhausted by his inability to move beyond the past. I do not want to end our friendship, but I also do not want to keep pretending that this behavior is normal or healthy. Should I apologize for the way I spoke to him, or was I justified in finally telling him that it is time to move on?