I have an old friend from school who I’ve known for 20 years.

Now mid 30’s. Unmarried, unsuccessful etc… He’s feeling insecure about where he’s at in life. Which is understandable. 

When we first met he was the most popular kid in school and I was lower status than him. 

Now in adulthood he can feel that he’s  lower status than I and he will make random digs at me in an effort to make himself feel better. 

Little immature things like “remember that girl you liked freshman year, she used to like me more”. lol sounds dumb to even type, but that is where this dude is at emotionally. Stuck in high school.

I love the guy like a brother, but the insecurity thing is kind of ruining the vibe every time we hang out.