Suggest songs for my friend's situation?
 

IDK, I just want to help him by making him listen to a certain music that fits him
Here's how his situation looks like:
Let's mention some pseudo-names.
My friend: Chris Brown
Girl: Rihanna
My friend's best friend: Chris Black
Chris Brown likes Rihanna. Chris Brown thinks Rihanna likes Chris Black. Chris Brown is confused because he said Rihanna stares at him every now and then (he has a feeling that she likes him too.) Chris Brown is nervous, so he can't tell Rihanna, but he is always sad when he sees Rihanna with Chris Black.
IDK, please suggest music for my friend Chris Brown.

Weezer's Pinkerton, maybe?
By the way, welcome to the forums. You should post something in the introductions forum (I forgot, but I wish I didn't).