Jude Law plays Danny Kowalski, a man who returns to the US to win the heart of his long-lost love, Nina Swan.
Jennifer Tilly portrays Nina Swan, the object of Danny's affection, who is hesitant to let him back into her life.
Gretchen Mol takes on the role of Anna Swan, Nina's sister, who becomes intrigued by Danny's romantic pursuit.
Martha Plimpton plays Karen Swan, another sister of Nina, who provides support and advice to both Nina and Danny.
Brenda Blethyn portrays Grace Swan, the matriarch of the Swan family, who has her own reasons for being wary of Danny.
Jon Tenney plays Eric, a friend of the Swan family who becomes an ally to Danny in his quest for Nina's heart.
Jeremy Piven portrays Billy, a close friend of Danny who offers support and comic relief throughout the film.
Vincent Laresca takes on the role of Jesus, a character who adds a touch of mystery and intrigue to the story.
Jane Adams plays Irene Swan, a member of the Swan family who has her own reservations about Danny and his intentions.
Bruce Jarchow portrays Richard Swan, the father figure in the Swan family, who is skeptical of Danny's return.
Kevin Kilner plays Hank Kowalski, Danny's older brother, who provides guidance and support to Danny throughout the film.
Jan Rubeš takes on the role of Louis Klammer, a character who adds a touch of charm and wit to the story.
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