I wouldn't say never, but neither Yes of course, because Chuck pushes everyone away, he doesn't let other people easily in. For Dan's side I think he could handle it, but I don't think Chuck could carry Dan as a best friend. They are way too different.

I hope for Dans sake that they never do.

I hope for Chuck sakes they never do. Dan would just ruin Chuck and make him boring like he did with Eric and Georgina

Dan Humphrey, as mari22 said, has a habit of ruining the characters he comes into contact with... Eric and Blair in the 2nd half of season 4, anyone? So no.

Also, can there be at least one person on the show who isn't obsessed with Dan Humphrey?

Hahahahaha no! They both like Blair, thats not gonna work!

Ehhh. Even if Dan stops liking Blair (which he should do) they will never be friends. They're just too different.

ehhh please chuck doesn't need friends like dan!

After what Chuck did to Jenny (and Blair) I don't want Dan to be friends with Chuck.
What kind of brother would be friends with the guy who tried to rape his sister, later took advantage of her, then only apologiezed so he could manipulated her/steal from her to ruin her college chances?

Dan Humphrey, as mari22 said, has a habit of ruining the characters he comes into contact with... Eric and Blair in the 2nd half of season 4, anyone? So no.

Also, can there be at least one person on the show who isn't obsessed with Dan Humphrey?

THIS SO MUCH!^^^

I'm curious, how has Dan ruined Eric and Blair?

By being there for them, when they needed someone and no one else gave a shit?

What kind of brother would be friends with the guy who tried to rape his sister, later took advantage of her, then only apologiezed so he could manipulated her/steal from her to ruin her college chances?

Idk, I guess the kind of brother who would fall for the girl who humiliated his sister time and time again ever since she was a freshman and banished her from her home.

Lol.

^this comment, so much