Among the many guests attending are Kevin MacEldowney (Philip Rayburn Smith), his wife Molly (Joy Gregory) and their friend Zane Levy (Joey Slotnick).

Among the guests are Duncan Shepard (David Caitlin) and Clay Mellon (Thom Cox), two mismatched best friends who are having their own life problems.

Electra and Holly are friends with Maria Goldstein (Teri Hatcher) who has become a wealthy business entrepreneur but who finds her own success to be lonely as well.

Grace Williams (Lara Flynn Boyle) is a demented practical joker who causes various mischief and mayhem at the reunion to anyone who slightly angers or annoys her, and who later hooks up with Clay after they bond over their similar life situations as both of whom hold a personal grudge against Robert Levitt.

The film also features cameo appearances by various actors and actresses whom include Molly Ringwald as a book fan of Holly's; Liev Schreiber as Fred Neff, a solo dancing attendee; Jennifer Grey as Polly Reed, a prescription medication addict; Carlos Jacott as the reunion's bartender; Helen Martin as a rude old lady that Clay and Grace encounter; and Marisa Tomei as Tori, another reunion guest.