Before he became president of the United States, Donald Trump was very much a part of the entertainment industry. He has a star on the Hollywood Walk of Fame, after all. As a result, just about everyone in Hollywood has a story about meeting the man who would soon lead the nation but who at the time was just a goofy television personality.
Many of these stories are now awkward and hilarious in hindsight, helping to paint a picture of Trump as someone you would never in a million years expect to ascend to the highest office. Here are some of the funniest and most awkward stories of celebrities encountering Trump before he was elected president.
1. Brooke Shields says Trump asked her on a date with a weird pick-up line
Brooke Shields says that Trump actually asked her out on a date once. This came in the 1990s after Trump’s divorce from his first wife, Ivana, she confirmed to The LA Times. Trump evidently called Shields and told her, “I really think we should date because you’re America’s sweetheart and I’m America’s richest man and the people would love it.”
Shields said no because she had a boyfriend at the time. But considering the disgusted look on her face while recalling the story on Watch What Happens Live, it’s clear that she wouldn’t have said yes either way.
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