As the story unfolds, the audience is introduced to various couples and individuals dealing with loss, showcased through nostalgic black and white photographs from the past. Set in the serene atmosphere of Boynton Beach, Florida, where retirement is the norm, we follow Marilyn as she enjoys her last morning with her husband, Marty. Unbeknownst to her, their time together is fleeting. Marty steps outside, swaying to the vibrant tune of "Papa Loves Mambo" by Perry Como, finding joy in an otherwise ordinary moment.
Tragedy strikes when a local woman, distracted by her cell phone while exiting her driveway, mistakenly believes she has struck a recycling bin, only to discover the grim reality that it was Marty. Following the funeral, Marilyn is greeted at the airport by her daughter, Denise, along with her husband and their grandchildren, Danny and Eric. To provide Marilyn with companionship during her time of grief, the family gifts her a small dog. Shortly after, Lois, an energetic interior designer, pays a visit. With a youthful spirit that defies her age, she extends an invitation to Marilyn to join a bereavement group.
As the story continues, we witness another funeral unfolding in a cemetery, where Molly mourns her grandmother, Phyllis. Months pass, and we follow Jack, Phyllis’s husband of over forty years, who joins the bereavement group led by Elaine. Amongst the members, he quickly bonds with Harry, while Lois reencounters Marilyn, assisting her with navigating the challenges of life post-loss, including driving, which Marilyn finds daunting.
In a light-hearted twist, Lois and her friends observe Donald, who catches their attention at a restaurant. He introduces himself as a real estate professional and later surprises them by covering their bill. Meanwhile, Harry experiments with online dating, meeting several intriguing women. At group meetings, Sandi expresses interest in Jack, while Harry attempts to teach him culinary skills, albeit with limited success.
As Lois diligently tries to help Marilyn drive, their comical attempts lead to near misses, such as when Marilyn almost collides with Jack's Mercury. Jack, accompanied by Sandi, is eager to arrive at the Chinese buffet before the crowds descend. Meanwhile, Linda, Jack’s daughter, and her daughter, Molly, sift through Phyllis’s belongings, discovering uncovered layers of her life through diaries that reveal her regrets and dreams.
At the community pool, Marilyn finds solace in watching families enjoying their time, but things turn sour when she spots the woman who changed her life forever. Lois and Donald finally embark on a date but face quirks such as the wind blowing their picnic sheet away. Harry's attempts at romance with Florence lead to comedic situations, including miscommunications about their intentions.
The emerging relationships reach a peak when Jack and Sandi end up in bed after a cooking mishap at Jack's house. Yet their connection faces challenges when Sandi's ex-husband unexpectedly reappears, forcing a conversation about her motivations for joining the bereavement group. At the same time, Lois reveals to Marilyn the complicated truth about her own life, hinting at loss and the search for closure.
As the holiday season looms, the bereavement group grapples with the impending celebrations, culminating in a fun plan for a 1950s-themed New Year’s Eve dance. Amidst these gatherings, Jack reevaluates his feelings towards Sandi, while Marilyn finds herself gradually adapting to her new life, eventually learning to drive and purchasing a cute Volkswagen Beetle convertible.
She confronts the woman responsible for Marty’s death, seeking understanding but ultimately receiving an unsatisfactory explanation. The finale draws near, with the group members gearing up for the New Year’s celebration. Both Lois and Marilyn, feeling the pangs of solitude, commit to attending the dance, where surprises await. They find unexpected connections, with Harry rallying the crowd into festivities, while Donald reappears, offering hope and rekindled interest.
Ultimately, Marilyn embraces her newfound companion, her dog, Oscar, and marks the end of her journey with a sense of acceptance and affection.
