Photo: Camera Press/Retna/Ikon Pictures/Pacific Coast News
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Prince William and Jecca Craig
Relationship: Dated in 2000
Although these two crazy kids were so infatuated with one another that they had a "pretend engagement" while they were dating, Wills and Jecca remained pals after their breakup. Jecca even went to Africa with Will and Kate in 2005 and was invited to the royal wedding, along with three more of Will's exes and one of Kate's.