Synopsis

Architect Oscar Novak is mistaken for gay by a wealthy businessman, who hires him to watch over his mistress. Oscar accepts the assignment to protect a valuable career opportunity, but soon falls in love with her. As the misunderstanding spreads through Chicago society, Oscar must choose between preserving his professional future and revealing the truth about his identity.

Factoids & Trivia

• Although the story is set in Chicago, the production filmed primarily in Toronto, using locations including the Distillery District, Liberty Grand, Canary Restaurant, and the Winter Garden Theatre.

• Principal photography took place from April 29 to July 3, 1998.

• The screenplay was based on an original story by Rodney Patrick Vaccaro, with later screenplay work by Aline Brosh McKenna.

• The film was produced with an estimated $20 million budget. Its domestic theatrical release began on October 22, 1999, and its domestic box-office total was approximately $10.6 million.

• A soundtrack album described as music "from and inspired by" the film was released by Atlantic Records on October 26, 1999. It featured swing-revival performers including the Brian Setzer Orchestra, Cherry Poppin' Daddies, and Mighty Blue Kings.

• The film received a PG-13 rating for sex-related situations and language.

• Its central comic device reflects a late-1990s romantic-comedy convention in which mistaken sexual identity drives the story, a premise later criticized for relying on dated gay stereotypes.