Jack & Jill (TV Series 1999–2001) - IMDb

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Jack & Jill: Created by Randi Mayem Singer. With Ivan Sergei, Amanda Peet, Jaime Pressly, Sarah Paulson. "Jack" moves to New York, and inadvertently steals the boyfriend office mate's "Jill", who is thinking of taking the next step with her girlfriend. Jack and Jill, romantically involved, face major obstacles in their current relationships.
"Jack" moves to New York, and inadvertently steals the boyfriend office mate's "Jill", who is thinking of taking the next step with her girlfriend. Jack and Jill, romantically involved, face major obstacles in their current relati