Patti Petalson (Selma Blair) is a promising writer, but her marriage and conventional job keep her from her dream. She longs to return to her writing, especially after running into her first love Brian Callahan (Patrick Wilson), a successful crime novelist. Kate (Debra Messing) is Patti's best friend since college. She's a tough-talking schoolteacher who plays therapist to all Patti's problems, while she's got a few of her own. Despite Brian's gorgeous Tribeca loft and perfect house in the Hamptons, he longs to write works of greater literary value. Michael Murphy (Edward Burns), his lawyer and best friend from college still carries a flame for his former girlfriend Kate, even though their relationship ended badly years ago. She holds a major grudge, but he would go to any length just to win Kate back, knowing his feelings for her never went away. He tried to forget over the years but since he spotted Kate in the restaurant she was all he could think about. When Patti sells Murphy a new apartment, and Brian publishes his personal novel, these old friends reconnect in unexpected ways with surprising results.

Cleveland Place and Kenmare Street, Manhattan.

McNally's Bookstore, 52 Prince Street and Mulberry Street, Manhattan.

Square Diner, 33 Leonard Street and Varick Street, Manhattan.

The Atalanta, 25 North Moore Street and Varick Street, Manhattan.

Brian's Apartment, 142 Duane Street and West Broadway, Manhattan.

Corner Bistro, 331 West 4th Street and Jane Street, Manhattan.

West 4th Street and Janes Street, Manhattan.

Queensboro Bridge, East 59th Street (btw Manhattan and Queens) New York.

Subway, Franklin Street and West Broadway, Manhattan.

Landmarc Restaurant, 179 West Broadway and Worth Street, Manhattan.

Cafe, 460 Greenwich Street and Watts Street, Manhattan.

Watts Street and Washington Street, Manhattan.

Madison Square Park, Madison Avenue and East 25th Street, Manhattan.

Prince Street and Mott Street, Manhattan.