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 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.

Rome tries to help Tyrell find a productive outlet for his frustrations about the racial issues in America while Regina is dealing with her mother's concerns regarding the future of Someday. Meanwhile, Katherine and Eddie struggle to navigate the waters of their relationship.

Maggie and Gary go to great lengths to entertain an unexpected visitor; Regina fears Tyrell is moving too quickly with a new love interest, and Rome supports a student who is ready to reveal their truth.

Maggie’s radio show is a proven success, yet she faces an uphill battle when her beliefs do not align with the station owners. Old wounds are reopened when Rome visits his old prep school and Katherine helps Eddie navigate the next step in his relationship with Anna.

Maggie receives some much-needed support from an unexpected source, Katherine grapples with her history with Shanice and her future with Greta; Rome faces off with his childhood bully and Sophie uncovers new information about Kai’s relationship with Peter.

Now that Maggie and Gary have found their way back together, they 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, and Rome’s documentary makes an impact on impressionable students at his old prep school

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 hits multiple roadblocks while trying to meet an important deadline; Eddie makes a surprising discovery at Katherine's house, and Rome struggles to connect with an impressionable group of young artists.

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.

Maggie is forced to face the harsh reality that cancer still controls her life, while Gary must choose between supporting a friend in need and building his relationship with Darcy. Meanwhile, Rome helps Regina at Someday during the COVID-19 transition

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.

Gary learns some new things about Maggie on their road trip to Albany. Eddie helps Rome in a time of need, and Regina sets boundaries with her father. Katherine reunites with someone from her past

Eddie is determined to prove that he can still be a good father despite his physical challenges, and Sophie searches for answers to help cope with her trauma. Meanwhile, Rome and Tyrell work together on a passion project.

As Gary once again acts as the glue that keeps this friend group together, he discovers that it is taking a toll on his relationship with Darcy. Meanwhile, Sophie leans on Rome to process her dad’s struggles and choices and how they might influence her own life

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.

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.

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.

Katherine realizes Theo is being discriminated against when one of his classmates asks him to wear a mask during Zoom school. Meanwhile, Regina finds her Vicodin is missing and suspects that Rome might’ve been the one to take them.

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.

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.

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.

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.

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.