Romantically Challenged premiered on ABC on April 19, 2010. What does it take for a bro to become a man? When an underachiever meets the girl of his dreams, he's going to have to figure out how to man up, keep the girl, all without losing his best bro. Shawn hasn't quite got his life all figured out. An aspiring writer and reluctant telemarketer, he's been living with his friend Perry in the hope that it will allow him to write the great American novel. This works out well for Perry, who's been feeling a little clingy since his ex dumped him over a year ago. But when Shawn meets Rebecca, his laid-back lifestyle is about to get a real shake-up. Rebecca is everything Shawn has been looking for. She's beautiful, successful, and totally gets his wry sense of humor. She's also got a few things he wasn't looking for like an ex-husband and two kids. Normally this would be the kiss of death for a commitment-phobic, responsibility-avoiding, underachiever, but Shawn thinks he might just be ready for a woman like Rebecca, insta-family and all. However, the big question is, can he start a life with the woman of his dreams without breaking up his 'bromance' with Perry?