why a person with such an remarkable life would be hanging out with them

That's a big part of it. And there is a reason for it. One I can't tell them and don't want to say here.

This is where I am at this point in my life. It's where I might be forever, who knows. I'm not saying I'm better than they are, several have done all sorts of cool shit on their own. But it's still a bit of that. What are you doing wasting your time here. Why don't you go here or here or here (people say that a lot). I'm happy where I am right now. This is where I need to be.

I guess if I explained to them the reason I'm here that would probably help this immenstely as they should immediately understand the disconnect they see between that person and this person. A lightbulb should go off. oooooohhhhhh that explains it.

But I can't. It's too private.

The other thing I would do is just tone it down on the stuff that people may not believe. So if you dated a b-list celeb, then just say his/her first name and emphasize why this person was crazy or why it didn't work out. People are interested in failure more than success. Emphasize stories vs a brag list. Instead of "I was once a professional surfer" say "I tried surfing once and was pretty decent at it so I thought I would enter the 'Big Kahuna' contest. I was super nervous, yada yada yada, and that's when a rogue wave took my swim trunks right off with everyone watching." The more details the more believable.

This is helpful thanks. I would have just said 'i tried surfing once' and like one more sentence. i don't elaborate on anything. self-conscious that people want to continue listening so I speak quickly and try to keep it short then shut up and let other people talk. I'll try to work on that when telling those stories (instead of bragging).

tldr: evidence, stories, failure, humility

I like it. Thanks.