The preposterous setup and Heather Graham's thoroughly unconvincing performance combine to turn a potentially interesting twist on the classic romantic triangle into an unbearable exercise in rom-com contrivance.
Manhattan siblings Gray (Graham) and Sam (Tom Cavanagh), are so a tight pair that new acquaintances often think they're married: They share an enormous loft apartment, jog together in Central Park and do elaborately choreographed dance numbers for seniors. Between their busy jobs — he's a surgical resident and she's an advertising executive; — and the time they spend together, they don't have much time to date, but know they should make an effort to get out more. So they borrow a pooch and cruise the dog park, where they meet the gorgeous Charlie (Bridget Moynahan), who's just relocated from San Francisco. Charlie and Sam form an instant connection; he proposes on their first date and they fly to Vegas for a quickie wedding that same week, with Gray in tow as their witness. The trouble starts when Gray, who constantly laments the fact that men just don't get her, shares a brief drunken pre-wedding smooch with Charlie. The kiss makes Gray question her sexuality, though her therapist, Dr. Sydney (Sissy Spacek), suggests that she's just jealous because she's no longer the center of her brother's attention. Gray decides to suppress her feelings for other women, but after a string of lousy dates and awkward kisses with men, her friendly frequent cabdriver and confidant Gordy (Alan Cumming) — who harbors a huge crush on her — encourages her to begin dating women and tell Sam what's going on. Both prospects overwhelm Gray, but she takes a deep breath and tells Sam — who's initially supportive until the moment when his sister admits to having made out with his wife. And so Gray must tackle the unfamiliar waters of a completely new dating pool without her brother's support.
Writer-director Sue Kramer is clearly out to shake up the boring old boy-meets-girl formula, but her movie is so filled with preposterous coincidence and ridiculous clunky plot machinations — Charlie and Gray's Las Vegas duet with Gloria Gaynor, their soberly shared soak in the hotel tub, surgical resident Sam's well-rested demeanor, Gordy's fortuitous appearances, the bottomless pool of dating prospects — that it's impossible to ignore them and focus on the equally contrived story. Molly Shannon is grating as Gray's closest coworker, and Spacek is underutilized (though impressive as a rock-climber). The only bright spots are Cavanagh's easy charm about him and Cumming's performance as Grody — he's much more believable as a straight man than Graham is as a gay woman. --Angel Cohn
