Romantically Challenged (TV Series)

TV Series (2010). 1 season. 4 episodes. From the writer of such irreverent and bold television shows as Family Guy and Politically Incorrect comes a comedy about four romantically challenged friends in their early thirties navigating their way through today's tricky world of dating. Smart and beautiful Rebecca Thomas (Alyssa Milano) is recently divorced after 15 years of marriage. Having never really dated before she was married - and not having been on a date since Clinton was in office -- she finds it scary to start over now. Although a gifted mom and lawyer, she is clueless about dating and hopes to get some help from her equally romantically challenged friends. Perry is Rebecca's best friend since childhood. He is a rugged man's man and a tremendously successful financial planner -- but also one of Pittsburgh's most sensitive hopeless romantics. When it comes to matters of the heart, Perry is a romance-aholic who falls in love with women 20 minutes after meeting them. After 40 minutes, he's already naming their future children. A struggling novelist, the witty and affable Shawn has been Perry's best friend and rent-free roommate for six years. Shawn is the emotionally unavailable cynic to Perry's hopeless romantic. He has never had a relationship more serious than a three-night stand - and even those send him running for the door. Rounding out the group is Rebecca's petite, baby sister, Lisa. Behind her deceptively sweet appearance is a sassy pit bull ready to protect her older sister. Although a nurturing kindergarten teacher, she has a wild side too, and sees a "threesome" as "second base." Will these four romantically challenged friends ever find lasting love? Or even someone who lasts until next Thursday?