Donald Trump and Barbara Walters during the Annual March of Dimes Gourmet Gala at the Plaza Hotel in New York City, 1989.
Time Life Pictures / Getty Images
Donald Trump and Faith Daniels attend the Fifth Annual Gourmet Gala March of Dimes Benefit on November 2, 1992 at the Plaza Hotel in New York City.
Ron Galella / WireImage
Donald Trump attends Playboy Magazine 40th Anniversary Press Party on May 3, 1993 at the Plaza Park Hyatt Hotel in New York City.
Ron Galella / WireImage
Donald Trump, Paula Zahn and Richard Cohen attend the Fifth Annual March of Dimes Gourmet Gala Benefit on November 2, 1992 at the Plaza Hotel in New York City.
Ron Galella / WireImage
Ron Galella / WireImage
Ron Galella / WireImage
Donald Trump and Miss Universe contestants enjoy the day on The Spirit New York Cruise in New York City, New York.
Ron Galella, Ltd. / WireImage
Ivanka Trump (center, in white) sits on her father Donald Trump's lap during a Beach Boys concert at the Mar-a-Lago estate in Palm Beach, Florida in 1996.
Davidoff Studios Photography / Getty Images
Ron Galella / WireImage
Donald Trump attends a Miss USA and Miss Teen USA Pageants Press Conference on January 7, 1999 in New York City.
Ron Galella / WireImage
Miss Universe, Venezuela's Alicia Machado, kisses Donald Trump during her daily fitness workout at a health center in New York, 1997.
Jon Levy / AFP / Getty Images
Donald Trump is flanked by Victoria Silvstedt, the 1997 Playmate of the Year, and his then girlfriend, Melania Knauss, at Playboy magazine's 50th anniversary celebration at the Lexington Ave. armory in 2003.
New York Daily News Archive / Getty Images
NEW YORK CITY - FEBRUARY 23: Cheryl Lee Ralph and Donald Trump attend Starlight Foundation Awards Gala on February 23, 1989 at the Waldorf Hotel in New York City. (Photo by Ron Galella/WireImage)
Ron Galella / WireImage
Donald Trump makes out with his then girlfriend Melania Knauss at the Men's Health Magazine Bash for the 50th Birthday in 2004.
New York Daily News Archive / Getty Images
Donald Trump and Playboy Bunny during the Betsey Johnson Spring 2001 Fashion Show at Bryant Park in New York City.
Ron Galella / WireImage
Ron Galella / WireImage
Ron Galella, Ltd. / WireImage
Pamela Anderson and Donald Trump get cozy as they attend a special, "Donald J. Trump Birthday Quarter Million Dollar Giveaway" celebration on June 11, 2005 in Atlantic City, New Jersey.
Donald Kravitz / Getty Images
Jennifer C, Donald Trump, Melania Knauss during a viewing party for The Apprentice 2: The Fashion Episode, in New York City, 2004.
M. Von Holden / FilmMagic
