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Hollywood's May-December Couples

35 of 40

Demi Lovato (22) and Ryan Phillippe (39)

Age difference: 17 years.

The couple was rumored to be dating in the summer of 2011. The relationship ended when Lovato discovered Phillippe was expecting a baby with an ex-girlfriend. —XFINITY Entertainment Staff (Photos by Frederick M. Brown; Frazer Harrison/Getty)

The opinions expressed are solely those of the author and do not necessarily reflect the views of Comcast.

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