Donald Trump Jr. And Kimberly Guilfoyle

When Donald Trump Jr. and Kimberly Guilfoyle first met, Barack Obama was still an Illinois senator, Don Jr.’s dad was a reality star, and the iPhone had just been invented. Suffice it to say, it’s been a slow burn for the MAGA it-couple. Trump and Guilfoyle operated in similar New York City circles in 2007, and their kids even attended the same private school. At the time, Trump was happily married to Vanessa. Guilfoyle, meanwhile, had recently tied the knot with businessman Eric Villency after divorcing California Democrat (and current governor) Gavin Newsom. Suffice it to say, romance wasn’t yet in the air for the couple.

In 2007, Kimberly Guilfoyle was a Fox News host and outspoken conservative — she had previously worked as an attorney in California but moved to New York after her first marriage came to an end (she divorced her second husband in 2009). In 2018, the TV personality was ousted from Fox after sexual harassment charges came to light at the height of the #MeToo Movement. According to one former employee, Guilfoyle engaged in a series of inappropriate workplace behaviors, requesting massages and showing off explicit pictures of her sexual partners, per The New Yorker. These allegations didn’t affect the host’s budding relationship with Don Jr., however. That same year, Guilfoyle and Trump went public with their romance.