Unsure how to navigate (M28,M28,M28)
I’m looking for perspective on a friendship dynamic that’s been bothering me lately.
There are 3 of us (all 28M) who have been friends since high school, so about 14 years now.
Over the past decade, our lives went in very different directions. I became a lawyer and recently got married. One of my closest friends is building a successful career in IT security and has a great family as well.
Our third friend struggled more with direction after high school. He dropped out of college early and has spent years bouncing between interests, jobs, and ideas without really committing to anything long term.
What makes this emotionally complicated for me is that I genuinely tried to help him over the years.
I went with him to college orientations, helped him research programs, talked through career ideas, encouraged him toward paths that matched his talents, etc.
He’s honestly a very talented artist, and at different points I encouraged him toward art/design work, commissions, online sales, and even programming certifications when he became interested in tech. But nothing really stuck because he never consistently followed through.
Now we’ve been invited to our 10 year high school reunion, and my other friend and I began to sort of talk about our accomplishments and wondering where everyone else ended up and yeah maybe we ended up bragging a bit.
After which my close friend privately told me he thinks we should be careful not to talk too much about careers, marriage, accomplishments, or life progress around him because he might feel bad or left behind.
I’m conflicted because I don’t want to make anyone feel small or excluded, especially someone I’ve known for most of my life. But at the same time, I also don’t want to feel like I need to minimize my own life or avoid normal conversations about what’s happened over the past decade.
For me, the difficult part is that I don’t really judge people based on money, status, or prestige. What I value most is perseverance, effort, initiative, and the willingness to build something meaningful for yourself even if progress is slow.
Over time, I think I’ve emotionally disconnected a bit because it started feeling like he stopped trying altogether, despite having talent and people willing to support him. I think that difference in values is what’s creating tension for me internally more than the actual career or financial differences.
At the same time, I still care about him as a longtime friend and don’t want to become overly judgmental or cold.
For people who’ve experienced this: how do you maintain old friendships when everyone’s lives evolve very differently? And where’s the line between being considerate versus feeling like you have to walk on eggshells around someone?