These Celebrities Had Super Awkward Encounters With Donald Trump

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.

Next: This celebrity was mocked by Trump for his height.  

2. After meeting George Clooney, Trump went on TV and made fun of his height

George Clooney in 2015

George Clooney | Neilson Barnard/Getty Images

George Clooney says that he met Trump once about 10 years ago. Clooney was out to dinner, and Trump approached him. They talked for a little while, with Trump telling Clooney he’d recommend him a doctor to deal with a neck issue.

That was the end of it. But then Trump went on Larry King Live and made fun of Clooney’s height, telling King that Clooney is “very little.” Clooney says that this “made me laugh.”

Next: This comedian tried and failed to get a photo with Trump. 

3. Norm MacDonald asked Trump for a picture, and Trump just walked away

Comedian Norm MacDonald says that he once met Trump while they were both on a talk show. This was during the presidential election, so Trump was surrounded by the Secret Service.

In the few minutes between acts, MacDonald says he asked Trump for a picture. Trump replied, “Ah, you’re funny. I love ‘ya. I’ll take a picture with you in a minute.” Then he turned around, got in an elevator, and never came back.

Next: This celebrity was given fake platinum cufflinks as a gift by Trump. 

4. Charlie Sheen says Trump gave him fake platinum cufflinks as a wedding gift

Charlie Sheen said during the 2016 election that he wasn’t a fan of Donald Trump. But that wasn’t just for the expected reasons; Sheen said that he also dislikes Trump due to a personal experience with him.

As Sheen explained on The Graham Norton Show, he was out at a dinner one night when Trump approached him, saying he wanted to give Sheen a wedding gift (even though Sheen says Trump was not invited to his wedding). Trump then pulled off the cufflinks he was wearing, which he said were platinum diamond Harry Winston, and gave them to Sheen.

About six months later, Sheen went to get some jewelry appraised, and he found out that the cufflinks were fake. “And I just thought, ‘What does this really say about the man?'” Sheen asked.

Next: This celebrity got some weird advice from Trump backstage at a talk show. 

5. Daniel Radcliffe says Trump gave him weird advice on a talk show

Daniel Radcliffe says that when he was 11 years old, he was getting ready to go on Today. While he was there, he met Trump, telling the businessman he was very nervous and not sure what he was going to say on the show. Trump responded, “You just tell them you met Mr. Trump.”

Recalling the story on Late Night with Seth Meyers, Radcliffe said he can’t relate to this level of confidence. He also found the idea of going on a talk show and spending your entire appearance talking about the guy who was just there a few minutes ago hilarious.

Next: This celebrity was pursued by Trump even though she had a boyfriend. 

6. Salma Hayek says Trump tried to get her number from her boyfriend

In another example of Trump attempting to woo a famous celebrity, Salma Hayek says that Trump tried to date her. As she explained on The Daily Show with Trevor Noah, she was once at an event with her boyfriend. When she got cold, she says that Trump immediately came over and put his coat on her. He then turned to Hayek’s boyfriend and said, “I’m sorry, your girlfriend, I saw she was cold.”

Hayek says that Trump and her boyfriend continued to talk, and Trump invited him to dinner. The boyfriend brought Hayek and Trump got both of their numbers, but he never called the boyfriend again, so it became clear to Hayek that this was just a way of getting her number.

She says that Trump subsequently called her and invited her — just her — to an event. When Hayek reminded him that she has a boyfriend, Trump apparently said, “He’s not good enough for you.”

Next: This celebrity says he had a bad experience running into Trump at a party. 

7. Richard Dreyfuss says Trump got annoyed at his date for speaking to his party guests

 Actor Richard Dreyfuss arrives at American Film Institute's 45th Life Achievement Award Gala Tribute to Diane Keaton

Richard Dreyfuss | Kevin Winter/Getty Images

Back in May 2016, Richard Dreyfuss went on a Twitter rant against Donald Trump, saying that Trump’s celebrity endorsers are “whores” and calling Trump an “unqualified racist.” He went on to share a story of meeting him.

Dreyfuss said that he was at a party in Malibu, where Trump “got very upset that his date had the [gall] to speak with other guests. He acted like a small d*cked prick and pusher from the party and left of us wondering if we had made a mistake [letting] her go with him.”

Dreyfuss has since deleted these tweets.

Next: This celebrity met Trump while wearing an elf costume.

8. Aubrey Plaza met Trump while wearing an elf costume

Aubrey Plaza has a pretty unique story of meeting the future president. As she explained on The Late Show with Stephen Colbert, when she was about 20, she was living in New York and working as a mascot. She dressed as the British children’s character Noddy.

One day, Plaza had a job at FAO Schwarz. She says that her boss told her that she had to get a picture with Trump that night or he would fire her. So Plaza tried her best to get a photo, but Trump didn’t want it. “He kept shooing me away,” Plaza said. “He didn’t want the picture. I kept dancing over to him trying to get the picture, and I finally just kind of put my creepy elf arm around him and forced him in there and got that picture.”

Plaza joked that if she knew then what she knows now, she would have tackled him to the ground.

Next: This celebrity says Trump tried to intimidate him. 

9. Jon Hamm says Trump tried to intimidate him at an SNL afterparty

Jon Hamm attends the "Mad Men" New York Special Screening at The Museum of Modern Art

Jon Hamm | Dave Kotinsky/Getty Images

Back in November 2015, Trump hosted Saturday Night Live, and Jon Hamm ran into him at the show’s afterparty. Hamm later told The New York Times that Trump and Bill O’Reilly tried to intimidate him.

“They’re both tall dudes,” Hamm said. “And I’m a tall dude. And they both do that tall-dude thing, which is try to intimidate you. And it doesn’t work on me. I’m like, ‘I’m as alpha as you. Let’s go. You’re not going to chest-bump me.’ It was a very weird night. It was the shortest I’ve ever stayed at an S.N.L. after-party.”

Next: This celebrity says that Trump hit on his wife at a party. 

10. Billy Baldwin says Trump hit on his wife

In November 2017, Donald Trump Jr. tweeted about multiple women accusing Senator Al Franken of sexual harassment. This struck some as hypocritical, considering the president himself has been accused of sexual harassment and assault. So Billy Baldwin responded to Trump Jr.’s tweet with a story.

In his response, Baldwin said he once had a party at the Plaza Hotel, which Trump owned. He says Trump showed up to the party uninvited and hit on his wife, inviting her to fly on his helicopter to Atlantic City. Of course, Baldwin says his wife rejected Trump. He also said that Trump is “a 5th degree black belt when it comes to sexual impropriety allegations.”

Next: This celebrity met Trump while goofing on him for his TV show.

11. Sasha Baron Cohen jokes he was the first person to dislike Trump after interviewing him in 2003

Sasha Baron Cohen says that he has the distinct honor of having disliked Trump long before everyone else did. Cohen interviewed Trump back in 2003 for Da Ali G Show. This was a show where Cohen would interview real people in character as Ali G, tricking them into thinking Ali G was an actual person and not an act.

So in 2003, Cohen interviewed Trump as Ali G. As part of the bit, he tries to sell Trump a business idea he has, but Trump doesn’t go for it. Trump ends up walking out of the interview, seemingly realizing it’s all a joke. Trump later tweeted about this, saying he walked out “immediately” and that this proves that he doesn’t fall for scams.

Cohen recalled this story on The Late Late Show. He joked that he was the “first person, actually, to realize that he’s a d*ck.” Cohen went on to dispute Trump’s account of events, saying he hardly realized it was a joke immediately.

“He claims that he saw through the interview,” Cohen says. “But actually, he was there for about seven minutes.”

Next: This celebrity met Trump when the future president made a cameo on his sitcom.

12. Peter Marc Jacobson says Trump had a hilarious request when appearing on The Nanny

Peter Marc Jacobson

Peter Marc Jacobson | Jason Merritt/Getty Images

Trump made cameo appearances in dozens of films and TV shows from the late 1980s into the 2000s. One of those was on the sitcom, The Nanny, in which Trump plays himself and is depicted as a highly important person who the main character runs into after her status is elevated.

When Trump started running for president, these cameos began earning new attention, and Peter Marc Jacobson, the co-creator of The Nanny, recalled meeting Trump for this cameo. He told Newsweek that Trump demanded a line be changed in the script. Jacobson explained:

We sent the script to Mr. Trump, and in return I got a message from casting that said, “Mr. Trump has a problem with the line above: ‘Do all you handsome millionaires know each other?'” I was actually impressed and thought, “Isn’t it nice that he’s humble and doesn’t want to call himself a millionaire?” Then I read the rest of the note, and it said, “Since he’s a billionaire, he would like the line changed accordingly.”

NextThis celebrity did the walk of shame in front of Trump. 

13. Bethenny Frankel unexpectedly ran into Trump after a night out

Bethenny Frankel says she had an awkward run-in with Trump, though it wasn’t because of anything Trump did. She explained that she ran into the future president at 7:45 a.m. after sleeping over with a date. Much to her chagrin, Trump recognized her and said hello.

“He gave me a hug, and I was like, ‘Oh my God, I probably have the worst Skinny Girl alcohol breath,’” Frankel said. “It was the walk of shame! I might have done the walk of shame with the future president.”

Next: This celebrity says he never forgot two back-to-back encounters with Trump in the late 1990s. 

14. Mark Cuban says Trump made a condescending comment to him at a party

Andrew Ross Sorkin and Mark Cuban speak onstage

Mark Cuban | Michael Cohen/Getty Images

All the way back in 2004, businessman Mark Cuban shared the story of how he met Trump for the first time. It was at a party in 1999, and Cuban says that Trump told him and the person he was talking to that “someday, maybe we could sit up there with the rich people,” looking up at the second-floor patio. Cuban was already doing fairly well for himself back then, being the co-founder of a company,, with $13 million in revenue and which Yahoo would soon buy for almost $6 billion.

Cuban says he later took a meeting with Trump at Trump Tower, and he was shocked that virtually every inch of Trump’s office was covered in pictures of himself. He says this left a lasting impression. “After leaving your office, I promised myself that if I ever got liquid and had an obscene amount of money in the bank, I would make a point not to remind myself and everyone else around me of it every minute of every day unlike you,” Cuban said.

Next: Trump reportedly hit on this member of the British royal family.

15. Princess Diana reportedly said Trump gave her the creeps

Princess Diana | Torsten Blackwood/AFP/Getty Images

Yes, President Trump supposedly hit on none other than Princess Diana herself, shortly after her divorce from Prince Charles. Diana never told this story publicly, but journalist Selina Scott made this allegation in The Sunday Times.

She says she was working on a documentary about Trump in 1994, and she personally witnessed Trump bombard Diana with bouquets of flowers and handwritten notes after her divorce. This was after Trump privately said Diana seemed like “a handful.”

Scott says that at a dinner, Princess Diana told her about the flowers, saying, “What am I going to do? He gives me the creeps.” Years later, Trump was interviewed by Howard Stern and bragged that he could have had sex with Diana.

Read more: The Most Fascinating Things You Never Knew About Donald Trump’s Childhood

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