How to deal with a friend who is making himself look pathetic?

Got this guy, been friends since highschool and we've been hanging around again recently, told him to come over my house tomorrow. But even if he's probably my truest friend, I'm having a problem with him.

On certain situations he's prone to making himself look pathetic from bad taste silly jokes that's part of our usual conversation and especially on what I would say his futile eagerness like what he was doing with the girl he's courting that he would say these lame things, not being discrete with the things he gives her, tries to impress her on things he may not be good at, gets obviously unmotivated when she's not around and tries to do his plan even if that would look silly to me and probably something his mom wouldn't like either. Because of those I told him flat I would not support his efforts on that girl.

He has phoned me a lot recently for advice when he has nothing to do, sometimes even twice a day. We've had lengthy conversations at night. Sometimes it went well and others I had to cut short with an excuse cause has was asking these lame things and opening up lame topics.I had to give up.I have strongly warned him not to say these type of things to a girl over the phone as that will turn away the girl. Some girls before have either turned him down or dumped him by the way.This guy has low self-esteem. I'm also that way so I understand he too needed an escape. I just don't know how long I can keep this up being a counselor to him. He needs help. I cant do it all.