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.

After discovering she might not know Rome like she thought she did, Regina is put in charge of making important decisions for him. Meanwhile, Gary tries to convince Maggie he will be there for her no matter what, and Katherine discovers she has a new admirer.

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.

On the verge of becoming a filmmaker, Rome takes a meeting with an old producer friend which causes him to feel torn about the creative changes he suggests for his script. Meanwhile, Gary steps in to help Danny prepare to audition for his school play, while Delilah craving some adult time agrees to go to dinner with Andrew.

It’s been three months since Delilah and Eddie revealed the truth about their affair, and Sophie continues to rebel against her mother. Maggie, Gary and the gang gather for the opening night of Danny’s play, and Rome and Regina take steps toward adopting a baby.

It's the first anniversary of Jon's death and everyone reflects on how much their lives have changed over the last year. But for Eddie, his dream opens up a new mystery.

Katherine discovers a possible connection between Eddie’s accident and Alex’s mysterious death. Meanwhile, Rome seeks help to address some pent-up anger issues, and Maggie continues on her journey of self-discovery in England. As Delilah prepares for her trip, Gary helps Danny confront a bully at his school.

Regina is faced with making difficult changes to keep Someday afloat during the COVID lockdown, while Eddie struggles to keep his secret drug addiction under wraps. Elsewhere, Maggie fears she may have revealed a bit too much on her podcast.

Gary's dad connects with Darcy about his personal experience from the Vietnam War. Meanwhile, during a dinner hosted by Rome and Regina, the video of George Floyd's murder is released, and they watch together in shock.