“I have a deal with her. She’s 17 and doing great — Ivanka. She made me promise, swear to her that I would never date a girl younger than her,” Trump said during a taping of Howard Stern’s radio show in June 1999. “So as she grows older, the field is getting very limited.”
“The nerve of her. Now you can’t go out with 16-year-olds,” Howard Stern joked in response.
He was dating the 26 year old Melania at the time.
Speaking of which, this interview with Melania in 1999 after she appeared on Howard Stern is really something. When Trump was stumping for a potential Reform Party run in 1999 he yelled, "where's my supermodel?" from the stage at a town hall meeting at the University of Pennsylvania.