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.

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.

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.

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.

A fellowship opportunity for Maggie forces Gary to reconsider his own future as the group must come together after a devastating loss.

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.

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.

When Eddie reveals his truth, Katherine suffers the consequences again. Rome and Regina offer support to Tyrell and his mother, and Maggie and Jamie are forced to address their relationship.

When Sophie is distraught after a disturbing encounter, Gary calls in Maggie and Regina for support; Eddie makes an unexpected friend.

Despite her trauma, Sophie goes through with her music school audition but quickly realizes she is struggling to move forward. Meanwhile, Rome and Regina grow closer to Tyrell. Katherine and Eddie are at a crossroads, and Gary reconnects with his father.

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.

In response to the killing of George Floyd, the group of friends are forced to reevaluate their own racial biases and take to the streets of Boston. Rome opts out in favor of his mental health and has a candid conversation with his father about how to effect change.

Gary’s past starts to affect his future with Darcy, while Eddie uncovers more from the night of his accident. Rome receives promising interest for his documentary, and Maggie gets a taste of workplace politics

Gary’s attempt to make things right for Sophie comes with unexpected repercussions. Eddie realizes Nicole needs help in her own ways, and Maggie connects more with Jane. Katherine discovers something new about herself.

The family of friends gathers once again to celebrate the life of a loved one who dies unexpectedly. Meanwhile, Katherine shows Maggie the secret to registering for baby gifts, and Rome supports his father through a difficult transition.

An unexpected fan steps behind the mic at Maggie’s radio show, and Walter attempts to convince Rome he is more than capable of being behind the wheel. Meanwhile, Eddie makes moves to reenter the dating pool and gets some help from an unexpected ally.

The ladies treat Maggie to one last hurrah before the baby’s arrival, and the guys attend a Bruins game for the last time. Meanwhile, Eddie toys with the idea of going back to college and Rome anxiously awaits news about his father.

Gary and Maggie gain much more than breathing techniques at their birthing class. Meanwhile, Rome and Regina’s quest to hire a caregiver for Walter takes an unexpected turn, and Theo learns a tough life lesson from an unlikely duo.

Maggie and Gary explore the possibility of a home birth, while Regina and Rome adjust to life with their new roommate. Katherine and Greta reach a crossroads in their relationship.

Regina and Rome face challenges living with Walter, while Eddie cautiously navigates his friendship with Nicole. Gary reunites with a relative who provides a new perspective on the past.

Secrets are revealed when Katherine meets Greta’s parents. Maggie returns to unexpected changes at her workplace. Rome and Omar reluctantly come together to make an important decision.

Gary feels the weight of his first Father’s Day as a new dad and his first without his own father. Eddie deals with an emergency. Meanwhile, Rome searches for a suitable environment for Walter.

A tight-knit circle of friends is reminded that friendship is a million little things.