Ironically, Vanessa had once briefly dated Donald Trump himself before she was introduced to his son. According to past interviews and reports, she had a few interactions with Donald Trump Sr. in the early 2000s, but the relationship didn’t last. Shortly afterward, she was introduced to Donald Jr. by the elder Trump at a fashion show. That twist of personal history has become more notable with her recent relationship with Tiger Woods, another man famously associated with Donald Trump.