Were really close friends but never hang out. How should I ask him?

My friend and Skyler and I met at work after I saw his fbook picture through friends and said to myself "theres something about this guy I cant stop staring at his picture, i want to know him" and that next month my boss brought this guy in to be my new cubemate at work for the summer...and it was him. We became the best of friends, are so much alike, he quit to go back to school 2 hours away, and we stayed friends. Only he never asks me to hang out. he doesnt date either because he wants to date when he knows he loves the girl and hasnt found her. Hes told me im the only other person in the world he can talk to about anything and who understands him and hes said he'll always be there for me. Im afraid to ask him to lunch or to hang out because he usually just hangs out with his guy friends. I dont really get it. I dont want him to shoot me down either. Hes 21 now so maybe some drinks would be cool one evening. Any advice!? I just miss him and chilling with him, i want someone to chill with thats that cool! He doesnt have a job and lives with his parents like 20 mins away from me for the summer, so he probly will say he doesnt have money and probly thinks its not convenient since he lives 20 mins away from where all the college bars in town are..should I offer to pay since I didnt see him for his bday in april?