10 Things You Should Know About Donald Trump

4) He Was Once Rumored to be Dating Anna Nicole Smith(4 of 10)

4) He Was Once Rumored to be Dating Anna Nicole Smith(4 of 10)

Yep, back in the early 90’s, Trump was in between marriages and back on the street trying to regain his title of Manhattan’s Most Eligible Bachelor.

He met Smith at a party and was reportedly quite taken with her.  The rest is unconfirmed Page Six history.