The Donald Trump-Debra Messing feud is maybe, partially, about an unrequited crush

Donald Trump had a big, pathetic crush on Debra Messing, and that’s why her Twitter hate hurt him so badly—at least, that’s one of the headlines out of Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, by Variety co-editor-in-chief Ramin Setoodeh. Rolling Stone has an excerpt from the book (which is out today) in which Trump expressed betrayal that Messing came after him on Twitter when she used to be so nice to him in the good ol’ NBC days.

In the excerpt, the former president recalled meeting Messing at his first-ever NBC Upfronts presentation (where the network pitches the TV season to advertisers). “She came up to me with her beautiful red hair,” he told Setoodeh, who reports that Trump “[paused] on this detail a beat too long.” In Trump’s memory, Messing gushed that he was “saving the network, and you’re saving my show.” Trump was starstruck because “I’ve been watching her” on Will & Grace, and here was a beautiful celebrity being “so thankful” to him. “And I’m saying, ‘She’d do anything for me,’” he reflected, his words “lathered with a suggestive grease, similar to” the infamous Access Hollywood tape, Setoodeh writes.

Trump simply could not square that someone who was “so effusive” in her gratitude would turn on him when he entered politics. (“She probably wouldn’t even admit it” today, he asserted: “She came up to me in front of a group of people. I’ve never seen it. She was begging for acceptance!”) “She was just a nasty person. Her and many others. So many people have come up to me over the years and said, ‘Thank you!’ Once I ran for office, that stopped.”

Well, duh! Actors like Messing are probably used to flattering slimy entertainment industry bigwigs for the sake of their jobs, but that doesn’t mean she’d endorse him for president of the country. Plus, Messing’s show was off the air by the time Trump launched his campaign, so she certainly didn’t have to pretend to be network buddies anymore. (The show came back in 2017, and used Trump’s presidency as a punchline.) Anyway, whether you think it hypocritical or not, Messing ultimately became a very vocal and visible critic of the ex-reality star during his presidency.

In a separate conversation, Trump brought up Messing again, admitting that he did have a crush on her in the early Will & Grace days—which gave context to why, of all the celebrities who were posting their distaste for the president, Trump targeted Messing in particular. (“Bad ‘actress’ Debra the Mess Messing is in hot water. She wants to create a ‘Blacklist’ of Trump supporters, & is being accused of McCarthyism.”) “This Debra Messing, who I always thought was quite attractive — not that it matters, of course . . .” Trump said to Setoodeh. “Debra Messing was so thankful,” he says. “And then I watch her today, and it’s like she’s a raving mess.”