Gary, Rome and Eddie discover that Jon really thought of everything before his passing by planning a surprise outing for Gary’s birthday at a Bruins Fantasy Camp. However, when a grave secret is exposed, Gary’s special day takes a turn for the worse as it creates conflict for everyone in the group.

On the eve of the new restaurant opening, Delilah tracks down a handsome expert to help with the last-minute details. Meanwhile, Regina struggles with her overbearing mother who causes friction by bringing up disturbing details of her past.

As her friends anxiously await the outcome of Maggie’s surgery, an unexpected arrival from her mother leads to a tense first meeting with Gary.

Gary accidentally crashes Maggie’s first date with a new guy, and Delilah is forced to have “the talk” with Sophie. Rome has an important meeting with a Hollywood big shot, while Eddie teaches Dakota a tough lesson in what it takes to succeed in the music business.