Mark, an old college friend, drops back into Jake’s life when he goes through a difficult divorce and looks to Jake for tips on re-entering the singles scene.

Meanwhile, Jake’s other old college friend, Adrian, begins to feel like the third wheel he was back in the day; Jake thinks a guys night out is exactly what he needs as he tries to forget Annie – despite the fact that she mysteriously keeps calling him -- and Naomi tries to juggle her crazy work life with motherhood.