Factual error: David Hyde Pierce mentions the Cuban Missile Crisis, which took place in October 1962. The time of year in the movie isn't entirely clear, but given the weather conditions it's almost certainly spring or summer, or several months before the Cuban Missile Crisis.

Down With Love (2003)
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Directed by: Peyton Reed
Starring: Ewan McGregor, Renée Zellweger, David Hyde Pierce, Sarah Paulson
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Peter MacMannus: Catch, you are the best friend a guy with twenty diagnosed neuroses ever had.
Catcher Block: Oh, we've been friends a long time... I knew you when you only had twelve.
Trivia: Near the beginning of the film, Catcher Block makes the remark that Barbara Novak didn't sound like a blonde over the phone. As it turns out in the end, Barbara was not a natural blonde at all.
Question: When the start credits are playing, is it Renee Zellweger and Ewan McGregor singing?
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Answer: No; Holly Palmer and Michael Bublé.
Rooster of Doom