Drew dives head first into the dating world with the help of a matchmaker, while Tara gives it a go with a popular Texas radio host. Courtney picks herself up by the bootstraps and agrees to resolve the awkward first meeting with Neill. Matt enters uncharted territory spending time with a single mom, but still finds himself in a more familiar setting on a dinner date with a triad of beautiful women. Glenn sees the results of his hard work in the pictures from his modeling shoot.