Dear Captain Awkward,

I am a middle aged man, married 22 years with a son. My former best friend and I lived next door to each other , we became friends when I was 9 years old. We continued to be the best of friends into adulthood.We went on vacations with other friends and with our wives. When we got married, we were each other’s best man. We attended each others kids birthday parties, etc. up until 2003-2004.

In 1997 I was a manager at a large securities firm on Wall Street. My best friend was working in a hotel at the time, had no financial background or college education. He called me up desperate-essentially begging me to help him get a job as he wished to marry his girlfriend and start a family but could not afford to do so on his salary. Due to my position and influence in the company I was able to help him get a job working in my department. Later I left the company and moved on to a more prestigious firm which paid better. My best friend reached out to me again and once again I was able to help him increase his income by getting him a job in my department.

The first couple of years, things were fine. In fact I felt we became closer as we now had one more thing in common. My friend was younger than me and our relationship was similar to a big brother/little brother interaction. He would come to my desk and hang out at the end of the day and wait for me to finish my work-just so we could walk a few blocks together on the way home (we lived in different cities by this time) we would also have lunch together several times a week and email back and forth throughout the day.

About three years later, I noticed that my friend had become a bit distant. He stopped coming by my desk during the day. He stopped emailing and when I emailed him, he would not always reply or say that he was too busy to chat. I asked several times if anything was wrong- But he always denied it . After a few weeks of this,We sat down face to face -and I again asked him to tell me what the problem was. He claimed he was just very busy and had some problems at home which he would not elaborate on, and he reiterated that it had nothing to do with me. This only made things worse for me, as we had always been open with each other about our problems and now he was holding things back. All of this took its toll and with the tensions of working closely together, we began having arguments at work. At first these were minor disagreements which would quickly blow over. But things began to get more serious and eventually we had a huge fight. We both went too far and I felt bad about it. This took place right before I was leaving on a family vacation.When I returned home I checked my email and found one from my friend notifying me that the friendship was over. I was shocked that he would take things this far after 25 years and also very upset that he would be so heartless as to do this with a one sentence email offering no explanation.

Although we had unquestionably both made mistakes, the thought of losing his friendship was just devastating to me, so I took full responsibility for the fight that we had and apologized profusely and repeatedly. I was desperate . I emailed, called and left a note of apology on his desk. I heard nothing for three days. Then he called me at my desk and invited me to go to lunch. I was relieved, I apologized a few more times and he told me not to worry about it. By the end of the lunch hour we were laughing and joking as though nothing had even happened.

As it turned out that was the last time we spoke face to face. A few days later he once again stopped speaking to me. I repeatedly asked why , and he offered little explanation, only saying he thought we needed a break. I strongly suspect that inviting me out to lunch that day was a cruel vengeful tactic on his part- just to make me think we were cool, and then cut me off again. I accused him of this a year later and not surprisingly he denied it.

I tried for the next few years to get him to explain his actions. I cannot understand to this day how he could end a 25 year friendship over what was basically a rough patch that we hit for a couple of weeks. He refused to explain or even respond to my letters or emails which were I admit increasingly angry due to the frustrating and hurtful behavior on his part. After three years of this I stopped contacting him.

In the meantime he has relocated to another part of the country and he is a Vice President . Although I have had a successful career and am well compensated, he has now achieved a position which I have never reached in my 28 year career. I find this particularly galling, since if it weren’t for me he probably would be working as a waiter or bartender , and now he has surpassed me in my career. Instead of being appreciative or grateful- he refuses to even speak to me.

The older I get the more I feel the expression “life is too short” and I recently attempted to contact him again. I contacted his sister via social media and asked her to try to get through to him. I made it clear-and this is 100% true-that I have zero interest in patching up the friendship. All that I really want-and I think I deserve it- is an explanation for all of this. Why did he treat me this way after all I had done for him ? Why did he do it in such a coldhearted manner? He declined through her- stating that he does not want to “re-hash” everything. The problem is he never gave a valid explanation in the first place. He has managed to avoid facing me like an adult about this for 14 years.

I don’t imagine there is anything else that I can do to try to get to the bottom of this but I would welcome any advice or suggestions as this continues to frustrate me 14 years later.

Thank you.

Hi there,

You say you are confused about why the friendship ended, but you tell me in your own words that when your friend told you he was preoccupied with problems at home that he preferred to keep private, you cornered him and pushed him to explain himself to you. You weren’t just his friend, you were senior to him in the company, and when he wanted and asked for some space, you refused to give it to him. That had to be extra hard for him because he risked not just your friendship but his job if he pissed you off, and yet, it was apparently worth it to him to risk that in order to get distance from you.

When you tell someone you don’t want to talk about something or that you need space and they ignore what you are saying to push for what they think should happen, it doesn’t bring you closer together. That last lunch you had together, which you interpret as a deliberate cruel trick he did to punish you could also be read as him trying one last time to see if y’all could just hang out without all the pushing and then deciding, “nope, I just gotta end it.”

This narrative you have, where he owes you his career, that he owed you information about his private family troubles, that he owes you explanations is the thing that is preventing you from being friends. You think he owes you something. He doesn’t feel the same way. He’s made it clear (a lot of times!) that he wants space from your friendship. That is the answer: “I don’t want to re-hash everything.” And yet, you keep busting through those barriers and demanding explanations, now harassing his sister so that you can get the things you think you are owed.

Please stop pretending you don’t know what happened. It’s not actually complicated. Your friend decided ended your friendship and he told you he was doing that. The friendship wasn’t working for him anymore. You don’t have to understand or agree with his reasons for that to be true. As an outsider reading about this situation, it doesn’t sound like any explanation he could have given you at the time would have been enough for you. It would have been some version of “I think you’re an asshole, and here’s all the reasons why” or “Dude, sorry, but I just don’t want to anymore.” Either way, you would have tried to argue him into the ground about it. What could he tell you now that would satisfy you? At this point, just pick one: “He thought I was an asshole (even though I tried my best to help him) and that’s unfair and he’s wrong but it’s his choice, so, fuck him” or “He just didn’t want to be my friend anymore, I’ll never know why, but it’s his choice, so, fuck him.”

Like Mr. #1091, you need to tell yourself a new story. You gave your friend a wonderful boost in his early career, but he wouldn’t be where he is now professionally if he hadn’t also supplied his own hard work and talents along the way. You need to turn “He owes me” and “He needed me” into “I’m so proud of him and happy for him, I always knew he could do it.” You can send those thoughts out into the world about him without contacting him. (Reminder: He doesn’t want to be contacted, even if it’s to say nice things).

The feelings of regret and hurt and anger you’re having now aren’t his to solve. He’s not obsessed with you the way you are with him, and chances are he’s not measuring his life against yours the way you are measuring yourself against him. So you need to find a healthier outlet for dealing with those feelings (like working with a therapist or counselor) so that you can process them and finally let them go in a way that doesn’t demand compliance or a performance from him.

You sound lonely and like you miss him a lot. Your challenge now is to take the love you had for him and pour that into other social and professional connections. Start a mentoring program where you work. Spend time with your son and other members of your family. Take a class or sign up for a recreational activity (I hear axe-throwing is pretty fun!) or volunteer somewhere. Do whatever gets you out of your head and reminds you that there are people who will be happy to see you and value what you have to give.

Grieve this dude like he died, then tell yourself a new story. You had this friend, and it didn’t work out, but that wasn’t the end of the world. You’re the only one with the power to make this stop hurting so much, so use it, and let go.