Despite being a happily married mother of two, Kathy (Harley Jane Kozak) has always wondered what it would've been like to sleep with her high school sweetheart, Tom (Ken Wahl). Her solution: send her best friend, Emily (Elizabeth McGovern), to seduce him and report back with all the juicy details. This romantic comedy also stars Bill Pullman as Kathy's husband and Brad Pitt as Emily's artist boyfriend.