This is going to be a long one.
He's been stuck on this same girl since before I've even known him. Basically, when they split paths in college, she realized she doesn't like him at all. Now she uses him for cash and treats him like shit. He knows this, but refuses to quit talking to her. Says he won't stop talking to her until he gets a different girlfriend. Problem there is that he has absolutely zero confidence and self esteem. Usually tries to rely on his cash for these two things. Ie. He bought a motorcycle lately for the main reason "It will give him confidence and help him with the ladies." Three months later, he still has zero confidence and self esteem...and no ladies.
He periodically keeps dropping these sob stories on me about how girls don't like him, he's going to be alone forever, etc. Essentially, he tries way too hard to find a girl. Probably damn near nuts himself whenever a girl says Hi to him. Granted, he's not in the best of shape or anything, but I've seen way fatter and uglier guys get chicks that are leaps and bounds above this guys standards.
I've tried to help him. Been brutally honest, but he just doesn't get it. Thinking of letting him just sit in the dark for a while and not talk to him till he snaps into reality.