The Awkward Moment Donald Trump Brought Up Don Jr.'s Girlfriend's Ex-Husband Right in Front of Her

After the president's comment, at a fundraiser last year, "there was some awkward, tepid laughter around the room"

President Donald Trump — who doesn’t not act like a comedian during his rallies and fundraising appearances — hasn’t been shy about riffing on his oldest son’s new girlfriend’s formerly Democratic love life.

As recounted in the new book The Hill to Die On, published Tuesday, Trump once jokingly referenced Kimberly Guilfoyle‘s ex-husband California Gov. Gavin Newsom during a fundraiser in Washington, D.C., on Sept. 27.

Guilfoyle, a former Fox News host, has been dating Donald Trump Jr. since Don. Jr’s wife, Vanessa, announced she was divorcing him last March. (They finalized their divorce agreement at the end of last year; Vanessa has been publicly supportive of the pair.)

In an “hour-plus-long riff about politics, policy, sports, and culture” while speaking at the September fundraiser, according to The Hill to Die On, President Trump honed in on California’s largely liberal policies, which are at sharp odds with his own.

And he mentioned Newsom, who was on the verge of being elected governor.

“Kimberly, you know him, right?” Trump said, addressing Guilfoyle, who was at the event, according to The Hill to Die On.

“There was some awkward, tepid laughter around the room,” authors Anna Palmer and Jake Sherman wrote.

The White House did not respond to a request for comment on their book.

SkyBridge Capital Holiday Celebration
Kimberly Guilfoyle. Jared Siskin/Patrick McMullan via Getty Images
96th Annual National Christmas Tree Lighting Ceremony
Kimberly Guilfoyle (far right) seated next to Donald Trump Jr. near President Donald Trump in November. Oliver Contreras/picture-alliance/dpa/AP Images

Guilfoyle, 50, and Newsom, 51, were married from 2001 to 2006, overlapping with his time as mayor of San Francisco.

In January 2005, they announced their split, reportedly saying in a statement then: “Unfortunately, the demands of our respective careers have made it too difficult for us to continue as a married couple. Over the past 10 years, we have developed a tremendous bond of love and respect for each other. That will never change.”

However, one friend told the San Francisco Chronicle at the time, “It’s no secret that they have been leading separate lives. She’s on one coast, he’s on the other — how can you make a marriage work like that?”

Said another friend: “Were there problems? Yes — that’s pretty much been an open secret for months.”

Asked in September about Guilfoyle’s relationship with 41-year-old Don Jr., Newsom said, “I wish her well and them well. And we see the world, clearly, with a different set of eyes politically.”

In an interview with BuzzFeed last month, he was somewhat circumspect about whether President Trump ever directly referenced Guilfoyle’s new relationship while talking with him.

“We may have had a private moment on that conversation,” Newsom said, “which in and of itself, makes life just interesting.”

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