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Phoebe and David initially break-up due to David moving to Minsk in The One with the Monkey.

Then, in The One in Barbados, Phoebe and David break-up due to Monica and Chandler's 'meddling'. David was going to propose to Phoebe, due to some bad advice given by Chandler. Monica called Mike (Phoebe's eventual husband and ex-boyfriend at the time), telling him of David's plan. Mike flew to Barbados, proposed to Phoebe, and although Phoebe said 'no' to Mike, she broke up with David to get back with Mike.

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