As of writing this, he's 31 years-old yet still lives with his mom and has practically no life experience. The combination of his sheer stupidity, gullibility, and intense eagerness to get laid has resulted in him giving out his Twitter and Facebook passwords to guys pretending to be girls on these sites, and of course, his accounts get hacked. Opie, Anthony, and Jimmy have berated Bobo on their show when he tells them about his accounts getting hacked, with hilarious verbal beatings by the boys on O&A.
Even if you're a guy who's not a hit with the ladies, you should know that if you constantly call/email/Tweet girls you want to talk to, you're more than likely going to annoy them and push them away from you. Bobo seems to think that you're not going to annoy a girl you want to hook up with by Tweeting her several dozen (if not hundreds) times a day. He also think it's okay to put up pictures of his penis on his Twitter page.
Bobo also has a really unhealthy fixation on the New York Mets and his dog, a Schnoodle named Mr. Maloonigans.
Even though Bobo is a complete disaster, I think he makes for great radio on O&A, whether he's doing a bit for them or if he's calling the show, pestering the boys to be back on the show.
Here's one of my favorite Bobo moments on O&A, where he does a "one man band," waking up his mom and half-sister early in the morning.