When: 2007
After the split from Jessica Biel, Jeter was seen at a Bahamas nightclub grinding with Gabrielle Union to "Put It In Your Mouth." True Story. Her rep said the pair "are friends but did not hook up." Union denied the reports herself later on but sounded very open to the idea, stating, "If I were dating Derek Jeter, trust me I'd announce it to the world." Sounds like a perfectly executed hit-and-run to us.
Smash Probability: