In this romantic comedy of mistaken identity, Oscar Novak (Matthew Perry) and Peter Steinberg (Oliver Platt) are a pair of struggling but talented Chicago architects given the chance of a lifetime: Charles Newman (Dylan McDermott), an extremely wealthy business tycoon, is considering hiring them to design a multi-million dollar cultural center. However, Oscar and Peter aren't the only ones who've been asked to contribute ideas for the project; Decker and Strauss (John C. McGinley and Bob Balaban), two highly successful designers that Oscar and Peter used to work for, have also been approached by Newman, who thinks that a competition between the two teams would be good fun and good press. Oscar is determined to show his dedication to the job, so when Newman asks him to start keeping tabs on his girlfriend Amy (Neve Campbell), he's happy to oblige. Oscar proves a sad excuse for a private eye, and finds himself falling in love with the woman that he's supposed to trail. To complicate matters, Charles gave Oscar the assignment because he was sure that Oscar is gay, and he hasn't been shy about telling people; soon Amy is convinced, along with most of Chicago. And while Oscar doesn't want to upset Newman, he also doesn't want to start living a lie, especially one that would keep him away from the woman he loves. So when Oscar is named Chicago's Gay Professional of the Year, what's a (straight) guy to do? Three to Tango features such familiar TV faces as Matthew Perry from Friends, Neve Campbell from Party of Five, and Dylan McDermott from The Practice.~Mark Deming
I wouldn't recommend this to many people, 'cause obviously most people didn't like it, to put it mildly, and there ARE some moments in this film that almost make me cringe, but overall I found this film to be a very romantic tale of a man who is in love - really, IN LOVE, not just attracted to - his boss's mistress. Their love (mutual) comes through in enough scenes, which is more than I can say about such cornball fluff as SLEEPLESS IN SEATTLE etc.; and despite the occasional moment of humor seemingly created by a deluted teen (or an engenous 5 year old), there are ALSO many scenes of memorable humor and the nature of the story gives the humor enough well rounded meaning to keep this a fav of mine for years to come.