Starting Over

Phil Potter attempts to reconcile with his wife Jessica, but she is determined to pursue a new independent life as a singer-songwriter. Heartbroken, Phil decides to leave their New York City apartment with just a single suitcase, marking the end of his marriage.

Phil relocates to Boston, Massachusetts, to live with his brother Mickey. There, Mickey encourages Phil to join a support group for divorced men while his wife, Marva, offers a positive outlook on the potential for new beginnings after the end of marriage.

Renting an apartment in Boston, Phil attempts to create a sense of home but struggles with feelings of loneliness and sadness. He longs for companionship as he settles into his new life, still feeling the weight of his recent divorce.

While walking to Mickey's house for dinner, Phil has a tense encounter with a woman, who mistakens him for a stalker. Later, he learns that the woman is Marilyn Holmberg, a friend of Mickey and Marva, which leads to a chance at a romantic connection.

After Mike and Marva express their hope for Phil and Marilyn to hit it off, Phil asks Marilyn out on a date. Although she is initially hesitant and wary of dating a recently divorced man, Phil's honesty about his situation eventually leads to a dinner date.

Feeling encouraged, Phil finally joins the support group for divorced men. His first date in eight years with a woman named Marie is uncomfortable, prompting him to reach out to Marilyn for a dinner date afterwards, signaling a turning point in his post-divorce life.

As Phil and Marilyn's relationship develops, they share an intimate night together after Phil surprises her at her apartment. Despite the initial awkwardness and her feelings of frustration with Phil's sudden move, they solidify their bond.

During Thanksgiving dinner at Mickey and Marva's, Phil receives a call from Jessica, which creates tension. Marilyn leaves abruptly, feeling insecure about Phil's lingering feelings for Jessica, leading to a critical moment of doubt in their relationship.

Phil confronts Marilyn about their relationship after she reacts to the Thanksgiving incident. He asks her to move in with him, and she excitedly agrees, hoping to deepen their connection, marking a new chapter for them both.

On the evening they are set to celebrate their new living arrangement, Phil is shocked to find Jessica waiting in his apartment with Marilyn. This awkward encounter challenges Phil's feelings and complicates his decision between the two women.

During the drive to Jessica's hotel, she tries to rekindle their romance, flirting with Phil. However, as she sings a song dedicated to their past love, Phil realizes that his feelings for her are not as strong as those for Marilyn.

At a support group meeting, Phil confesses his lingering attraction to Jessica, which creates tension between him and Marilyn. An anxiety attack prompts Mickey's assistance, reinforcing Phil's internal struggle between his past and present relationships.

Feeling the pull towards Jessica again, Phil attempts to resume their relationship. However, constant disagreements remind him that he may not be as happy with her as he was with Marilyn, prompting a moment of realization.

Returning to Boston, Phil attempts to reconnect with Marilyn, who is now dating a basketball player. Undeterred, he proposes marriage to her at a Celtics game, which takes her by surprise and rekindles hope for their future together.

Overcome with emotion from the surprise proposal, Marilyn’s feelings for Phil are reignited. She embraces him, indicating her readiness to move forward with their relationship, bringing their journey full circle.