This documentary styled story with 'man on the street' interviews follows the lives of six interlinked characters of all ages, at different stages in their lives on an emotional love merry-go-round.
On the rebound, TV producer Tommy (Edward Burns) divides his time scoping out real estate and pursuing Maria (Rosario Dawson) the divorcee he met over a copy of "Breakfast at Tiffany's" in a video store. Maria's ex-husband, Ben (David Krumholtz), giving up on his ex-wife, spends his days pining after unavailable Ashley, (Brittany Murphy) the sexy waitress trapped in a tawdry affair with lecherous dentist Griffin (Stanley Tucci) who seems to be experiencing a mid-life crisis. Coincidentally the same Griffin is married to beautiful, stylish Annie (Heather Graham) who just happens to be Tommy's real estate agent!
Whilst slick seducer Carpo (Denis Farina) gives Tommy advice on how to score with the ladies the others are under pressure to find their own way over the hurdles of love, sex and commitment, leaving us wondering whether anyone really has the answers to all those relationship questions and whether the search for the ideal companion is all part of the fun?!