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.
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.
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.
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.
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.
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.
Delilah makes arrangements for a family photo shoot with longtime photographer Seymour, but Danny struggles to accept that this new family does not include his father. Meanwhile, Rome and Regina make big plans to celebrate Rome’s parents’ 50th wedding anniversary and are forced to take a closer look at their own marital woes; Eddie and Katherine look for a fresh start; and Gary feels disconnected from Maggie.
The gang gathers for Theo’s 10th birthday, which is also a significant milestone for Eddie. Meanwhile, Delilah, Eddie and Katherine are at an impasse about revealing the truth about Charlie; Rome and Regina try to keep Sophie from getting too close to PJ; and Maggie helps Gary make a difficult decision about his dog, Colin.
In the aftermath of Eddie’s car accident, Katherine leans on their beloved group of friends for support. Meanwhile, Rome and Regina face a tough decision about the future of their family, and Delilah sees how her kids are thriving and wants the same for herself. Maggie jump starts her new life in Oxford, while Gary continues to navigate his new relationship with Darcy.
Katherine and Theo learn to adapt to their new life after Eddie’s accident. Rome and Regina grow distant as Rome suppresses his anger over the failed adoption. Delilah struggles with having a date at the house while the kids are away. Maggie unexpectedly bonds with her new roommate as Gary navigates trying to stay friends with her while building his relationship with Darcy.
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.
As COVID-19 becomes more widespread across the United States, Boston goes into lockdown, putting Rome’s movie in jeopardy and forcing Maggie to return home from Oxford. Because the hospitals are overwhelmed with coronavirus patients, Eddie’s back surgery is canceled, leading him to take desperate measures to cope with the severe pain.
Gary struggles in the aftermath of his encounter with Peter. Meanwhile, Regina and Rome put on a united front following the closure of Someday and the deportation of Tyrell’s mother. Sophie deals with mixed emotions surrounding her mother while Delilah faces a difficult decision. Eddie inches closer to finding out who caused the accident, and Maggie navigates a new career opportunity.
Gary takes steps forward with Darcy and continues to distance himself from anything involving Peter. Rome makes an effort to distract Regina from her job search, which may be looking up after all. Maggie adjusts to a new work environment, while Katherine entertains a new friend. Eddie makes progress in more ways than one.
When the girls decide to throw Katherine a celebratory divorce party, the guys get together to watch the hockey game and distract Eddie. Maggie is blindsided by some news, while Sophie is forced to stand her ground. Eddie helps Theo with a romantic gesture for a new crush and stumbles into someone from his past.
Having found their way back together, Maggie and Gary take important steps to secure their future as a couple. Regina’s estranged parents reunite to support her new business. Katherine and Greta attend their high school reunion. Rome’s documentary makes an impact on impressionable students at his old prep school.