10 Years

The central figure who wrestles with proposing to Jess while revisiting his past with Mary. He seeks closure on old feelings but remains invested in his current relationship. Throughout the night, he navigates honesty, commitment, and the pull of his history.

Jake's girlfriend who notices his behavior around Mary and ultimately chooses to give him space for closure. She demonstrates patience and emotional awareness, supporting him while asserting her own boundaries.

Jake's high school sweetheart who is now married to Paul and unexpectedly pregnant. Her reunion with Jake rekindles old emotions and prompts a candid look at how their lives have diverged.

Host and old friend who gets drunk and struggles to apologize to former classmates. His antics trigger awkward moments but also moments of vulnerability and growth.

Cully's wife, present at the gathering, who shares in the celebrations and the friction of the night. She observes the group's dynamics and adds an anchor of domestic stability.

A famous musician whose performance of 'Never Had' acts as a catalyst for the night’s revelations, including a moment of connection with Elise.

A reclusive classmate whose presence at the reunion and the lyric moment with Reeves unlocks a long-suppressed memory. Her quiet demeanor masks a story of resilience.

Friend whose personal life includes a strong bond with his wife Olivia and a plan to return to Japan with Suki, illustrating the adventurous path some friends choose in adulthood.

Garrity's wife who admires his breakdancing and provides a supportive counterpoint to the group's more chaotic moments.

Former prom queen now a single mother who reveals her current struggles and finds common ground with Marty and AJ through shared life issues.

Jake's friend who paints a realistic picture of life in New York vs. his actual circumstances, adding depth to the night’s conversations about success and happiness.

Another friend who, alongside Marty, navigates financial and relationship pressures, contributing to the ensemble's sense of shared vulnerabilities.

Mary's husband, whose presence underscores the reality of her current life and the complexities of past relationships colliding with present commitments.

An adventurous friend who plans to return to Japan with his wife Suki, symbolizing the pursuit of ongoing exploration and new chapters in life.