Three to Tango was released in 1999, and is rated PG-13. Oscar Novak (Matthew Perry) and Peter Steinberg (Oliver Platt) are architects bidding on a multi-million dollar project funded by wealthy and eccentric Charles Newman (Dylan McDermott). They get a chance at the job, and Charles then asks/tells Oscar to spy on his mistress Amy Post (Neve Campbell). Charles believes that Amy is safe with Oscar, as he was told that Oscar is gay. Oscar does not realize when he agrees to the task that Charles thinks he is gay, which he is not.
Amy is a glassblower, and Oscar first meets her at an exhibition of her artwork. They hit it off right away, but Oscar can’t pursue her as everyone thinks he is gay, and if he told the truth about his being straight, he thinks it could cost him and Peter their job. So Oscar pretends to be gay, and becomes friends with Amy. What follows is a very fine, funny, romantic comedy. The message in the movie has to do with Oscar gaining notoriety as an openly gay professional, and him feeling what it must be like for gays who hide who they truly are from the world.
Graeme Revell wrote the film’s music, which features wonderful big band dance music for most of the film. Mr. Revell also wrote the score for
The Saint, a very different soundtrack, but also beautiful. The actors have great chemistry, particularly Neve and Matthew, and Dylan is so charming and odd at the same time. Kelly Rowan of 
The O.C. fame has a small role as Charles’s wife. The Chicago skyline is awesome day and night, as are the scenes along the waterfront. This movie really makes me laugh, and though not a typical Valentine’s Day romantic comedy, it is playful, and just plain great entertainment.
It is interesting to think about pretending to be gay. I think there are many stereotypes about gay men that someone could use to pretend, but I can't think of as many for gay women. Don't tell me what they are, though. It's probably better to have missed some of the stereotyping in the world!
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