Seriously, a good friend of mine has been having a really bad couple months. Love of his life taken from him, his beloved car having a lot of problems, trouble in school, getting too busy with work, and today his grandma guy, so he cancelled out on our plan to go see Borat and getting shitfaced. I really want to help him, and I've been friends with him for nearly half my short little life. But my relationship with him is really based on immature poking fun at each other thing. He's a really shy, uptight guy most the time. I just want to know how to get him to open up so i can talk to him about his problems.

what have you tried so far, and what has his response been? if you tell me that i can advise you better.

This kind of upsets me sometimes, but i always find that my friends and i talk about deeper/more personal things when we're drunk. It only upsets me sometimes because i wish we could talk about the same things when we we sober without adding all the "your gay" or other bullshit to turn it into a big joke.

So anyways, i guess i recommend just drinking with your friend and not at some big party, and just asking him how he's doing.