Allegra (Elizabeth Reaser), an opera-loving writer in New York, eschews commitment, so her girlfriend, Samantha (Julianne Nicholson), leaves her. Allegra misses Sam, and resents the accusation that she's afraid to say "I love you," but she's soon involved with two people - Grace (Gretchen Mol) and Philip (Justin Kirk) - who, unbeknownst to her, have just broken up with each other. Allegra juggles the two affairs, telling neither about the other; each likes her more and more as her old fears start making her itchy. Things come to a head at an engagement party where Allegra is pinch-hitting as a catering assistant.

Subway, West 12th Street and 7th Avenue, Manhattan.

Lincoln Center, Columbus Avenue (btw West 63rd and 64th Street) Manhattan.

The Iroquois, 49 West 44th Street (btw 5th & 6th Avenues) Manhattan.

Sheep Meadow, Central Park (btw 66th and 69th Street) Manhattan.

Conservatory Water Central Park, (from 72nd to 75th Street) Manhattan.

Cinema Village, 22 East 12th Street and 5th Avenue, Manhattan.

Tremont Restaurant, 51 Bank Street and West 4th Street, Manhattan.

Bleecker Street and Perry Street, Manhattan.

Bookshop, 304 West 4th Street and Bank Street, Manhattan.

Deli, 628 Hudson Street and Jane Street, Manhattan.

Subway, Christopher Street and 7th Avenue, Manhattan.

Christopher Street and Gay Street, Manhattan.

90 Bedford Street and Grove Street, Manhattan.

564 Park Avenue and East 62nd Street, Manhattan.

The Mall, Central Park, Manhattan.