Katie Holmes and Chris Klein
This cute couple started dating in 2000 and were engaged in 2003, but the engagement was called off in 2005. Klein said of the split, “We grew up. The fantasy was over and reality set in.” Weeks after the relationship ended, Katie Holmes started dating actor Tom Cruise and the rest was history... until she divorced Cruise in 2012. —XFINITY Entertainment Staff (AP Photo/Kim D. Johnson)
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