Bill Borgens (Greg Kinnear): A successful novelist who is struggling to move on after his wife, Erica, leaves him for another man. He grapples with his lingering feelings for her while trying to guide his children through their own romantic challenges.

Erica (Jennifer Connelly): Bill's ex-wife, whose departure has left a significant impact on the family. Her relationship with her children, especially her daughter Samantha, is strained due to the circumstances of her leaving.

Samantha Borgens (Lily Collins): The college-aged daughter who has adopted a cynical view of love, engaging in casual relationships to protect herself from emotional pain. Her outlook begins to shift when she meets Louis, who challenges her perceptions.

Rusty Borgens (Nat Wolff): The teenage son and aspiring writer who embodies the ideals of romanticism. He harbors a crush on his classmate Kate and experiences the trials of first love, which become complicated due to Kate's personal struggles.

Louis (Logan Lerman): Samantha's classmate who becomes romantically interested in her. His genuine and patient nature helps Samantha reconsider her stance on love and relationships.

Kate (Liana Liberato): Rusty's classmate and love interest who deals with her own set of challenges, including substance abuse and a tumultuous personal life. Her relationship with Rusty plays a pivotal role in both of their character developments.

Tricia (Kristen Bell): Bill's married neighbor and occasional romantic partner. She provides him with companionship and advice as he navigates life post-divorce.