Vince Vaughn plays Russell Durrell, a young attorney and single father striving to balance his work and personal life.
Monica Potter portrays Kate Durrell, Russell's former wife and the mother of their son, who is torn between past regrets and future opportunities.
Joey Lauren Adams takes on the role of Beth Ward, a free-spirited woman who becomes romantically involved with Russell, adding a layer of complexity to his life.
Devon Sawa plays Noah Ward, the teenage son of Beth, whose presence introduces new challenges and dynamics to Russell's already complicated situation.
Todd Louiso portrays Bob Harper, Russell's coworker and friend, providing some comic relief and moral support in the midst of Russell's struggles.
Jenny Robertson brings Joyce Ives to life, a character who offers a perspective on relationships and family dynamics that influences Russell's decisions.
Siobhan Fallon Hogan plays Charlotte, a small but impactful role in the film, contributing to the colorful ensemble of characters that shape Russell's world.
Chris Bauer portrays Larry Ives, a character whose interactions with Russell shed light on different aspects of fatherhood and responsibility.
Nicholas Campbell takes on the role of Frankie Gooland, a character whose presence brings about unexpected twists and turns in Russell's life.
Aleksa Palladino as Bonnie brings a sense of mystery and intrigue to the plot, adding layers to the story of love and personal growth.
Janet Kidder portrays Carol Holman, a character who plays a supportive role in Russell's journey towards understanding his priorities and desires.
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