Time Life Pictures / Getty Images

Donald Trump and Barbara Walters during the Annual March of Dimes Gourmet Gala at the Plaza Hotel in New York City, 1989.

Ron Galella / WireImage

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

Ron Galella / WireImage

Donald Trump snaps Polaroids of Playmate hopefuls for Playboy magazine in 1993.

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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.

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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.

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Davidoff Studios Photography / Getty Images

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.

Ron Galella / WireImage

Ron Galella / WireImage

Marla Maples, Donald Trump, and model Roshumba Williams attend the Second Annual DISHES Pediatric AIDS Benefit on August 10, 1996, at Atlantic Beach in Amagansett, New York.

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Ron Galella, Ltd. / WireImage

Donald Trump and Miss Universe contestants enjoy the day on The Spirit New York Cruise in New York City, New York.

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Jon Levy / AFP / Getty Images

Miss Universe, Venezuela’s Alicia Machado, kisses Donald Trump during her daily fitness workout at a health center in New York, 1997.

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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

Ron Galella, Ltd. / WireImage

Donald Trump and his then girlfriend, model Kylie Bax, at the premiere of Blade in New York City, 1998. Donald Trump with Miss New York and Miss Connecticut in 1999.

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New York Daily News Archive / 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.

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New York Daily News Archive / Getty Images

Donald Trump makes out with his then girlfriend Melania Knauss at the Men’s Health Magazine Bash for the 50th Birthday in 2004.

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Ron Galella / WireImage

Donald Trump and Playboy Bunny during the Betsey Johnson Spring 2001 Fashion Show at Bryant Park in New York City.

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Dimitrios Kambouris / WireImage for Full Picture

Katie Couric and Donald Trump during Entertainment Industry Foundation’s Colon Cancer Benefit in New York City, 2004.

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M. Von Holden / FilmMagic

Jennifer C, Donald Trump, Melania Knauss during a viewing party for The Apprentice 2: The Fashion Episode, in New York City, 2004.

Michael Caulfield Archive / WireImage

Donald Trump and Megan Mullally perform at the 57th Annual Emmy Awards in 2005.

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Donald Kravitz / Getty Images

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.

Ethan Miller / Getty Images

AP Photo / Rick Maiman

Donald Trump kisses Miss Universe 2009 Stefania Fernandez as they arrive at the 2010 Miss Universe Pageant at the Mandalay Bay Events Center in Las Vegas, Nevada, 2010 (left). Miss USA 2006 Tara Conner is kissed by Donald Trump after a news conference on December 19, 2006, in New York City.

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Michael Loccisano / FilmMagic

Melania Trump, Donald Trump, and Heidi Klum attend the worldwide launch of the Trump International Hotel & Tower Dubai on June 23, 2008, at The Park Plaza in New York City.

Denise Truscello / WireImage

Adam Ward / Newspix / Getty Images

Donald Trump and Miss USA 2009 Kristen Dalton pose for photos at the 2009 Miss USA Pageant in Las Vegas, Nevada (left). Donald Trump and former Miss Universe Jennifer Hawkins attend the National Achievers Congress at the Sydney Entertainment Centre on September 20, 2011, in Sydney, Australia (right).

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Kabik / Getty Images

Donald Trump and Miss Universe 2012 Olivia Culpo are pictured after the Miss Universe 2012 finals in Las Vegas, Nevada.

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Brendan Smialowski / AFP / Getty Images

Republican presidential candidate Donald Trump awkwardly embraces his daughter Ivanka Trump on the last day of the Republican National Convention on July 21, 2016, in Cleveland, Ohio.

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