The smart and beautiful Rebecca is recently divorced after 15 years of marriage, and hasn’t been on a date since Clinton was in office. Although a gifted mom and lawyer, she’s clueless about dating and hopes to get some help from her equally romantically challenged friends: Perry is Rebecca’s best friend since childhood, but he’s one of Pittsburgh’s most sensitive hopeless romantics. When it comes to matters of the heart, Perry is a romance-aholic. Shawn, a struggling novelist, is Perry’s best friend and rent-free roommate, but he’s never had a relationship more serious than a three-night stand. Rounding out the group is Rebecca’s baby sister, Lisa, whose sweet appearance belies the fact she’s a sassy pit bull ready to protect her older sister.
In the premiere episode, “Rebecca’s One Night Stand,” Lisa finally convinces Rebecca to have her first one night stand. But the always polite Rebecca violates Lisa’s number-one rule by calling her date, Leo, the morning after. Now Leo is into Rebecca, so Lisa gives her sister her own unusual brand of dating advice so Rebecca can break up with him. Meanwhile, an overworked Perry decides to take a stay-cation. But doing so gets on the nerves of his unemployed roommate, Shawn, to the point that Shawn decides to get a job – any job.
“Romantically Challenged” stars Alyssa Milano as Rebecca Thomas, Kyle Bornheimer as Perry Gill, Josh Lawson as Shawn Goldwater and Kelly Stables as Lisa Thomas.
Guest starring are Israel Broussard as Justin, John Brotherton as Leo, Edward Flores as Bob, Emayatzy Corinealdi as Tiffany, Elaine Loh as waitress, Brian Michael Jones as restaurant patron and Donald Li as owner.