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Ally McBeal is an American television series which ran on the FOX network from 1997 to 2002 and was one of the best-known "dramedy" television series of the 1990s winning several awards.
Jenny's mom's wedding is approaching, and Ally is shocked when Tim gives her a certain look that suggests a move. She talks to Jenny, and they decide to test him. Ally makes a move on him, and he offers her to have an affair.