This (Sad!) Pickup Line Trump Tried On Brooke Shields Will Make You Gag

Decades before any of us could in our wildest dreams imagine real estate developer, TV personality, and renowned misogynist Donald Trump would became the 45th President of the United States, he was using his charm and gentle tactility to ask a 1999 Brooke Shields on a date.

And when I say “charm and gentle tactility” what I really mean is “typical buffoonery and the worst pickup line ever uttered by any POTUS in history NO DOUBT.” Shields appeared on Watch What Happens Live and revealed to Andy Cohen that back in the blissful, pure 90s, Trump had approached her and asked her out on a date,

“I was on location doing a movie and he called me right after he’d gotten a divorce, and 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.'”


Shockingly, Shields declined. “I have a boyfriend, he’s not going to be happy about it,” the 52-year-old said. Although while discussing their meeting, her mouth is in a scary grimace and she shakes her head with such stiffness it seems as though she’s in a hostage situation. That’s diplomacy for you.

A Tale Of Diplomacy, In Four Parts:


Some other unfortunate Trumpisms on would-be girlfriends:

On his treatment of Princess Diana: “Trump clearly saw Diana as the ultimate trophy wife,” said veteran BBC TV journalist Selina Scott in The Sunday Times. “As the roses and orchids piled up at her apartment she became increasingly concerned about what she should do. It had begun to feel as if Trump was stalking her.”

On courting Emma Thompson: “I lift up the phone. ‘Hi, it’s Donald Trump here.’ I said, ‘Really? Can I help you?,’ and he said, ‘Yeah, I, just, you know, I wondered if I could offer you some accommodation in one of my Trump Towers. They’re really comfortable.’”

On trying to steal Salma Hayek from her boyfriend: He walked over and placed his jacket over her shoulders because she was cold, then ignored her and only spoke to her boyfriend for the remainder of the night. He never spoke to him again, but called Hayek and asked her out on a date. “He’s inviting me out, and I’m like, ‘What about my boyfriend? Am I crazy? Are you asking me out? You know I have a boyfriend,'” she said, before to which Trump responded, “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.”

Anyway. If all else fails, just start kissing them. Don’t even wait. Grab ’em by the pussy!