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

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.

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

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

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.

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.

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.

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

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.

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.

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 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.

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.

Eddie manages to keep Theo distracted in the midst of trying to track down Katherine, while Maggie realizes her mother’s surprise move to Boston might not be just for her. Meanwhile, Regina struggles with accepting Andrew’s ideas about the restaurant, and PJ makes a shocking confession to Rome.

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.