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Rent Sidewalks of New York (2000)

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 – "The Brothers McMullen", "She’s The One") divides his time scoping out real estate and pursuing Maria (Rosario Dawson – "Men In Black 2", "Josie And The Pussycats") the divorcee he met over a copy of "Breakfast at Tiffany’s" in a video store. Maria’s ex-husband, Ben (David Krumholtz – "The Mexican", "10 Things I Hate About You"), giving up on his ex-wife, spends his days pining after unavailable Ashley, (Brittany Murphy – "Girl Interrupted", "Clueless") the sexy waitress trapped in a tawdry affair with lecherous dentist Griffin (Stanley Tucci – "The Pelican Brief", "Deconstruction Harry") who seems to be experiencing a mid-life crisis. Coincidentally the same Griffin is married to beautiful, stylish Annie (Heather Graham – "Boogie Nights", "Austin Powers: the Spy Who Shagged Me") who just happens to be Tommy’s real estate agent!
Whilst slick seducer Carpo (Denis Farina – "Saving Private Ryan", "Snatch") 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?!