A group of friends from Boston who feel stuck in life experience an unexpected wake-up call after one of their friends dies unexpectedly.
They say friendship isn’t one big thing, it’s a million little things; and that’s true for a group of friends from Boston who bond under unexpected circumstances. Some have achieved success, others are struggling in their careers and relationships, but all of them feel stuck in life. After one of them dies by suicide, it’s just the wake-up call the others need to finally start living.
The group tries to be there for Sophie as an upcoming father-daughter dance recital approaches, and when she asks a very reluctant and arrhythmic Eddie to dance with her, it leaves Delilah feeling uneasy. Against her better judgment, Maggie agrees to have Rome in for a therapy session, but it quickly becomes clear that her new friendships are a conflict of interest. Meanwhile, Danny confesses a secret to Gary; Maggie receives an unexpected visitor from her past; and someone discovers a cryptic voicemail from Jon that was left right before he died.
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.
The aftermath of Eddie and Delilah’s secret takes a toll on everyone in the group, including the future of Delilah and Regina’s restaurant. Maggie and Gary’s relationship is tested when an old fling turns up, and Delilah struggles with the balance of protecting her children and keeping Jon’s memory alive.
Gary attempts to plan a romantic date with Maggie with the intentions of getting her to open up about a secret she has been hiding; Eddie begins to understand the sacrifices Katherine has made and attempts to stall Theo’s play as a grand gesture to win her back; and Rome takes steps to consult with a doctor.
Delilah grapples with her life-changing decision, Maggie and Gary babysit Theo, and Regina finds out Rome’s big secret.
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.
Recurring nightmares force Maggie to face a life-altering trauma from her past, while in real life, the group finally discovers that her cancer is back. Gary seeks help from an unexpected someone in order to make one final attempt at convincing Maggie to get treatment, but everything comes to a head at Regina and Delilah’s first tasting party at the new restaurant, leaving this circle of friends to wonder if things will ever be the same.
Gary has trouble dealing with Maggie’s life-changing decision, which takes him back to when Jon was there for him during his chemo treatments; Rome finally opens up to his dad about his internal struggles; and Katherine battles balancing being a working mother without Eddie.
With the holidays quickly approaching, Delilah struggles with telling Sophie and Danny about her pregnancy; and although Jon’s absence makes this time of year especially difficult, the gang comes together to help the Dixons embrace the Christmas spirit.
After troubling news, Delilah finds herself once again leaning on her friends in order to help her family, unexpectedly having to rely on Katherine the most out of all people. Despite Gary’s protests, Maggie insists on running the Suicide Prevention 5K with the rest of the gang, where Danny also plans to introduce someone special to his mom and sister.
We go back to the day before Jon’s death, before everything seemed to have fallen apart. Jon is struggling both in his personal and work life, Delilah and Eddie make plans to tell Jon about their secret affair, and Maggie attempts to start her new life in Boston.
Delilah struggles to find a way to keep the house, while Ashley has a secret meeting with someone who she thinks may be able to help; and Maggie receives news about her treatment.
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.
Eddie and Katherine’s divorce mediations become complicated, and Rome’s brother makes an unexpected visit. Meanwhile, Gary and Maggie attempt to check an item off her bucket list.
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.
With questions still lingering around Jon’s death, his loved ones try to move on, each taking meaningful steps forward in their own lives. As most of them begin to accept that they may never get the explanation they desire, an unexpected member of the group decides to dig even further into the mystery behind Barbara Morgan.
