Continuity mistake: From Katherine's office there is a beautiful view on a waterway (New Yorkers will know the name). In every scene there there is a lot of discontinuity regarding the ships and ferries appearing and disappearing, especially when Tess comes to the office the second time to take some notes. (00:16:10)

Working Girl (1988)
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Directed by: Mike Nichols
Starring: Alec Baldwin, Harrison Ford, Joan Cusack, Kevin Spacey, Melanie Griffith, Sigourney Weaver
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Katherine Parker: Ugh! What a slob.
Tess McGill: You were so smooth with him.
Katherine Parker: Never burn bridges. Today's junior prick, tomorrow's senior partner.
Trivia: Catherine tosses a huge black gorilla to Tess as she gets off the helicopter. This was an inside joke reference to "Gorillas in the Mist" which Sigourney Weaver had just finished filming and was released only three months before this movie.
Question: If Jack and Katherine were a couple, how is it that Jack doesn't recognize Katherine's office when he goes there to confirm him and Tess to start working on the Trask deal?
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Answer: Unless Katherine had recently moved to a new office, which it does not appear that she did, then Jack should know this was her office. However, it is also possible that he had just never been there before and they only saw each other outside of work. When Jack went to see Tess, he had a specific business reason for going there.
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