Donald Trump snaps Polaroids of Playmate hopefuls for Playboy magazine in 1993.
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.
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.
Donald Trump and Megan Mullally perform at the 57th Annual Emmy Awards in 2005.
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.
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).