Zimbio, in photo: Derek Jeter, girlfriend Vanessa Lachey
5. Derek Jeter dated Vanessa Lachey
November 2003 - March 2006

Derek Jeter and Vanessa Minnillo were first spotted courtside at a Knicks game together. This was the beginning of an on-again, off-again relationship that lasted until early 2006. The two reportedly remain friends.