Four friends in their early 30s try to navigate the tricky world of dating as they try to find love and happiness in Pittsburgh. Smart and beautiful Rebecca (Alyssa Milano – Charmed, Who’s the Boss) is recently divorced after many years of marriage, and, although a gifted mom and lawyer, she's clueless about dating and hopes to get some help from her friends — even though they are just as romantically challenged. Perry (Kyle Bornheimer), Rebecca's best friend since childhood, is one of Pittsburgh's most sensitive hopeless romantics. When it comes to matters of the heart, Perry is a romance-aholic, falling in love with women twenty minutes after meeting them. Shawn (Josh Lawson), a struggling novelist, is Perry's best friend and rent-free roommate, and has never had a relationship more serious than a three-night stand. Rounding out the group is Rebecca's baby sister, Lisa (Kelly Stables), whose sweet appearance belies the fact she's a sassy pit bull ready to protect her older sister.