drama about a try-hard

[tired_time]

A guy is trying hard to get a girlfriend, he has a board at home with all potential lovers and notes about them. He has friends with whom he plays basketball. He trains every day but is not the best player but makes a winning shot in some game to win a box of bear for his team. He tries to pick up a jogging women but she ignores him or something, so he runs really hard after her (despite her being way faster) until he's coughing blood or something. Then she agrees to have dinner with him but it doesn't work out. Most of the movie is about him being into another women who sleeps with one of his friends after. After that there is a dialog between friend and main character's crush like:
-maybe you should get dressed again?
-why?
-so you could undress again
Then she feels uncomfortable and leaves quickly.

Please help me, I've been searching for this a lot.

[tired_time]

not Silver Linings Playbook, but thanks for a try. Movie is from the 90s or something. It was not very original but I find myself thinking about it often because I feel similar to the main character.

[Jerky]

Sounds like some dreck that I've watched before. Maybe something starring Jonathan Silverman (post Weekend At Bernie's)

Maybe this? (don't remember much) : http://www.criticker.com/film/Two_Guys_ ... out_Girls/

[tired_time]

no, not Two Guys Talkin' About Girls. I've seen this movie, a bit of a similar feel, but not it. Read about almost all Jonathan Silverman movies, but again no:/ Thanks for trying