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The fifth season of Friends, an American sitcom created by David Crane and Marta Kauffman, premiered on NBC on September 24, 1998. Friends was produced by Bright/Kauffman/Crane Productions, in association with Warner Bros. Television. The season contains 24 episodes and concluded airing on May 20, 1999.

This season features Monica and Chandler trying to keep their new relationship a secret from their friends. Phoebe gives birth to triplets in the show's one hundredth episode. She gives birth to a boy, Frank Jr Jr, and two girls: Leslie, and Chandler (who they had originally thought was a boy, but decided to keep the name Chandler anyways). Ross and Emily's marriage is called off as Emily is intimidated by Rachel, and Ross is unwilling to give up his friendship with her as Emily demands. Phoebe starts a relationship with police officer Gary (Michael Rapaport). Monica and Chandler's relationship is eventually revealed to everyone and they decide to get married on a trip to Las Vegas, but change their plans after witnessing Ross and Rachel drunkenly stumble out of the wedding chapel.

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