Time and time again, stories of Donald Trump’s interactions with woman are delivered as truly embarrassing moments.

Shortly after he separated from his second wife, Marla Maples, Trump approached Brooke Shields with a pitch like no other.

Shields spilt the deets on Watch What Happens Live!, explaining to Andy Cohen how Trump tried to ask her out by bragging about being “America’s richest man”:

“I was on location doing a movie and he called me right after he gotten a divorce,” Shields said.

“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.’”

Awks.

The titbit came out after a round of ‘Brooke Fields’ and happens at the 2:21 mark, if you have no time to watch Shields guess who’s posing in the photos with her:

Of course, Shields isn’t the only woman to make it known she has rejected Trump’s advances. As TIME explains:

Candice Bergen said that she had an awkward first date with him and Salma Hayek also said that he had attempted to hit on her while she was with her boyfriend at the time.

And now he’s leading the land of the free. Goodness.

[source:time]