Big-Name Celebrities Who Trump Tried (and Failed) to Date

We all can remember a time when Donald Trump was more famous for his role in The Apprentice than he was for stirring the pot in the White House. And now with a Trump presidency, most have forgotten his past relationships. Yes, we know of his current marriage to Melania. And now his ex-wife Ivana Trump is also coming out of the woodwork. But three marriages aside, there are plenty of women Trump courted who are also big-name celebs we can’t forget.

Let’s take a quick look at seven of them (surprisingly, relationship No. 6 managed to last for two years). We also include a bonus relationship that Trump failed at playing matchmaker.

1. Trump used an awful pickup line on Brooke Shields

Brooke Shields poses in a red dress while staring to the side.

Brooke Shields turned him down quite nicely. | Dave Kotinsky/Getty Images

Even our president isn’t immune to the embarrassment of a bad pickup line. Trump reportedly hit on Brooke Shields back in 1999 following his divorce from his second wife, says HuffPost. According to Shields, he said, “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.”

So, what was her response? She told Trump she had a boyfriend who probably wouldn’t appreciate his advances.

Next: A jacket in the cold leads to a phone call without the boyfriend.

2. He gave Salma Hayek his jacket when she was cold

Salma Hayek sits on stage and stares straight ahead at the audience in front of a panel.

Salma Hayek was not into his advances. | Vittorio Zunino Celotto/Getty Images for DFI

It turns out if you’re cold and in the same venue as Trump, he might just throw his jacket over your shoulders and ask you out later. As Salma Hayek says, Trump offered up his jacket to her at an event and then started talking to her boyfriend, People reports. Trump allegedly then said to her boyfriend, “I’m sorry, your girlfriend, I saw she was cold,” and then continued the conversation as if nothing happened.

Trump then asked for both of their phone numbers so he could invite them to his hotel in Atlantic City. Only one person ever received a call, though, and that was Hayek.

Next: This famous actress had no chemistry with Trump.

3. Candice Bergen had no chemistry with Trump on their date

Candice Bergen smiling and posing in a red suit and rope necklace.

Candice Bergen had a not-so-exciting date with Trump. | Christopher Polk/Getty Images for Turner

You may know Candice Bergen from her Emmy-winning performance on Murphy Brown, but you should also know about her awful date with our president. The Los Angeles Times reports Bergen and Trump went on one date in college. She says he “was wearing a three-piece burgundy suit and burgundy patent leather loafers and in a burgundy limousine.” Bergen also notes there was no physical contact the entire time, and she returned home early.

Next: Trump creeps out a famous princess

4. Trump said seriously creepy things about Princess Diana

Princess Diana standing in front of photographers.

Would Princess Diana have turned down a date with Donald Trump? | Vincent Amalvy/AFP/Getty Images

It turns out our president had a thing for Princess Diana. According to news presenter Selina Scott, Trump creeped Princess Diana out with his massive bouquets of flowers he would leave for her at Kensington Palace, says MSN News. And after her death, Trump reportedly told his friends his biggest regret was that they never dated.

Unfortunately, the madness doesn’t end there. Audio from 1997 just months after Diana’s death exhibits Trump saying he thought she was crazy, but he “would have had sex with her anyway.” He also joked about giving her an HIV test.

Next: This Oscar-winning actress never called Trump back.

5. Emma Thompson never called Trump back

Emma Thompson smiling in a black shirt at a movie premiere.

Emma didn’t find his offer very enticing. | Ben A. Pruchnie/Getty Images

Remember Emma Thompson from her Oscar-winning performance in Sense and Sensibility? Vanity Fair reports Thompson was the object of Trump’s desire back in 1997. He called her trailer phone while she was on the set of Primary Colors and said, “I want to offer you accommodations in one of my beautiful establishments and maybe we could have dinner sometime.”

Thompson thought Trump was very strange for ringing her, so she said she’d call him back about the proposition — and then never did. Instead, she laughed about it to her friends.

Next: Trump dated this model for two years.

6. Trump dated model Kara Young for two years

Kara Young walking down a fashion aisle.

Kara Young found his recent remarks appalling. | Paul Hawthorne/Getty Images

Many folks in the U.S. have pointed out some of Trump’s racist comments and actions during his presidency, so the fact that he dated someone who isn’t white may be surprising. Inside Edition reports model Kara Young and Trump dated before he courted Melania. They met at a party in the Hamptons in 1997, a time when she was busy modeling for Victoria’s Secret and Playboy in Germany. Trump has even praised Young post-breakup, saying, “You know, she’s really a fantastic girl.”

Young says she never heard Trump make any racist comments through the years — but as for his remarks about the violence in Charlottesville, she wasn’t too impressed.

Next: The cause of Trump’s first divorce?

7. Carla Bruni was rumored to have caused Trump’s first divorce

Carla Bruni poses at a red carpet in a black dress.

They didn’t get very far in their relationship. | Julien M. Hekimian/Getty Images

There were rumors flying left and right about the former first lady of France and our current president. According to People, the rumors stated Carla Bruni’s relationship with Trump was the reason behind his divorce to his first wife, Marla Maples. Trump even perpetuated the rumor by allegedly acting like a publicist and confirming the rumors to then-People reporter Sue Carswell.

Bruni denies anything ever happened to this day, and Trump has since said the whole thing was a joke taken too far. Either way, we have no idea what really went on and perhaps never will.

Next: Trump failed at getting his daughter set up with this star.

8. Trump tried (and failed) to play matchmaker

Tom Brady was amazing in Super Bowl 51. | Ronald Martinez/Getty Images

We know Trump is friends with Tom Brady, and Brady himself has described Trump as a “friend,” but once upon a time ago, Trump supposedly tried to play matchmaker with the New England Patriots quarterback and his daughter, Ivanka Trump.

According to Trump’s first wife, Ivana Trump, Donald wanted Ivanka to date Brady. In her book Raising Trump, she writes, “At one point, Donald wanted her to date Tom Brady, the quarterback. He said, ‘You have to meet him!’ But Ivanka wasn’t into it.”

Furthermore, Anthony Scaramucci, Trump’s former White House Communications Director who lasted only 10 days, believes Gisele Bündchen prevented Brady from visiting the White House after the Patriots latest Super Bowl win because the supermodel, Brady’s wife, didn’t want him near Ivanka.