Donald Trump Dropped the Most Awkward Pickup Line to Ask Brooke Shields on a Date

Decades before Donald Trump became POTUS and married wife, Melania Trump, the real estate mogul was apparently making passes at another model with some pretty cringe-worthy pickup lines.

While appearing on Watch What Happens Live with Andy Cohen on Tuesday, supermodel Brooke Shields recalled the time she rejected the former Apprentice star after one particularly awkward attempt at scoring a date with her nearly twenty years ago.

"I was on location doing a movie and he called me right after he had gotten a divorce," the 52-year-old recounted of her conversation with Trump, who finalized his split from his second wife, Marla Maples, in 1999.

The Blue Lagoon actress admitted that Trump's reasoning for the date is what really put her off. "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,'" she revealed.

Her response? "I have a boyfriend, he's not going to be happy about it."

Shields joins a long line of famous leading ladies, including Princess Diana, Emma Thompson, Candice Bergen, and Salma Hayek, who have claimed that they were once courted by the current commander in chief.