Donald Trump's Attempt At Taking Brooke Shields On A Date Was Super Awkward

Donald Trump has a reputation for being a little, to put it nicely, hands-on with women, so it's no surprise that at one time he asked out none other than actor Brooke Shields. Shields, who once suffered through a bad date with JFK Jr., gave Andy Cohen the full details of her bizarre interaction with Trump during an appearance on "Watch What Happens Live." 

As part of a fun segment on the show, Cohen and Shields played a game where he showed her a bunch of photos she'd taken over the years with famous people, and one of them was none other than Donald Trump. When Trump's photo with Shields came up, which she recalled being taken at a charity event, the actor looked disgusted and even gagged while looking at it. 

When asked by Cohen if Trump was flirty with her, Shields said no before quickly adding that he did ask her out at a different time. She was then pressed by Cohen for more details, delighting the studio audience. 

Brooke Shields elaborated: "I didn't go out [with Trump], he called me. I was on location doing a movie, and he called me right after he had gotten a divorce." She added, "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.'" When the interaction happened, Trump had recently divorced Marla Maples, and Shields was dating someone else.

Despite her clear disgust at seeing the photo of them together, Shields let Trump down rather nicely at the time, telling him, "I have a boyfriend, I really don't think it would be — he's not really gonna be happy about it." It's common knowledge that the former president has a reputation for being less than polite to women, so Shields' recollection that he didn't hit on her at the gala is surprising. 

Still, the actor seemed more than relieved that she had an excuse to give him when Trump did actually ask her out. It isn't just Shields, either. The controversial politician has quite a trail of women who have rejected his advances, including fellow Hollywood heavyweights Emma Thompson and Salma Hayek.

According to W magazine, Donald Trump's attempt to ask Emma Thompson out happened in 1998, as the actor recounted on a Swedish talk show. Trump contacted Thompson and offered her a stay in one of the Trump Towers, despite having never met her before. When the Oscar winner asked for clarification on what Trump was implying, he responded with: "Well, I think we would get along very well — maybe have dinner sometime." Extremely confused, Thompson told Trump she would call back, though she never actually did. 

As for Salma Hayek, she told Trevor Noah about her interaction with Trump on "The Daily Show." While the actor was out with her boyfriend, Trump got both of their numbers and extended an invite to one of his resorts. Later on, Trump called Hayek to directly ask her out, to which the stunning star responded that she had a boyfriend (the same one Trump had previously met, in fact). 

Hayek then claimed that Trump insulted her boyfriend, stating, "He's not good enough for you. He's not important, he's not big enough for you. You have to go out with me." It seems that the former president's preferred method of hitting on women is to offer them a stay in one of his many real estate investments — though clearly, it's not entirely successful.