What does it mean when a guy keeps comparing himself to other boys?

Sometimes when people compare themselves to others, it could either mean they are uncomfortable in their own skins, envy of the other person or to make themselves feel better. People can be very competitive. He could feel like other guys appearances are better than his, he is envy of a certain person or he is self conscious.

It depends. When he compares himself to other guys, is he saying he's better than them at everything? Or does it sound like he thinks that a lot of guys are better than him?

With either of those, it means he's a little insecure. If he's bragging that he's better than everyone else, that's really easy to get tired about hearing of. Bragging is a kind of insecurity, but its also poor manners. A person should let their actions speak for themselves, not tell everybody in the world about it.

If it seems like he worries that other boys are better, or smarter, or better looking than him, that's kind of sad, but also boring after a while. In that case you could just say that everybody is different and you like that, or else the world would be so boring and it wouldn't be as much fun meeting new people.

However, he might be trying to get you to tell what kind of boys you like. He might want to know if you like a boy like him. Do you like him? If you do, do you like him-like him? Or just like him like a buddy? Because if you like him in that special way you could let him know either by Words, saying 'I like you silly'. Or maybe you could be a little brave and next time he says that stuff, you could reach over and hold his hand.

But if you like him just as a buddy, but he likes you like a girlfriend, its a little hard not to hurt their feelings if they are into you, but its way easier to let them know now, than it is later on. You could say something like I wonder what kind of guy I'll end up liking when I'm older? But one thing I do know is that you're my friend and being friends is cool enough..