Vanessa Trump’s feelings about Kimberly Guilfoyle surprised many — especially after it was revealed that Guilfoyle and Donald Trump Jr. were cozy for a considerable time before he signed on the dotted divorce line in February 2019. “Don and I knew each other for years, but when we went on one date years later, that was it, Sparks,” Guilfoyle told Metropolitan Palm Beach magazine in December 2022. “In fact, we have been together from that night on, happily ever after!”
Vanessa and Donald Jr.’s marriage was reportedly over long before Guilfoyle entered the picture. “I heard for a while they have been living separate lives… Even before all this Trump presidency stuff started, they weren’t good, and their marriage was strained,” a source close to the couple told People in March 2018.
After news of their relationship broke, Guilfoyle quickly became a regular fixture at Donald Jr.’s side as he toured the country on his father, Donald Trump’s campaign trail. By New Year’s Eve 2021, the couple was engaged to be married. “Tonight was extra special celebrating @donaldjtrumpjr’s birthday. Don, you are strong, smart, courageous, funny, and the love of my life. I can’t wait to spend the rest of our lives together. Love you,” she captioned a photo of them smiling in front of a Christmas tree, her giant sparkler on full display.
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