‘Does Vanessa Have Some Black in Her?’ Tiger Woods’ Guest List Was Stacked, Yet Vanessa and Kai Trump’s Matching Looks Had Fans Doing a Double Take
Tiger Woods and Vanessa Trump are still going strong, and Vanessa's daughter, Kai Trump, seems to be on board with their new relationship. The couple have been dating for over a year after meeting through their kids, who attend the same school. Together, they have a full and blended house with seven kids. That family connection was on full display recently, as Vanessa and Kai both turned heads at the golfer’s celebratory event, making a noticeable splash in Palm Beach while showing up to support and mark the legend’s special day. Vanessa Trump and her daughter, Kai Trump, attended her boyfriend, Tiger Woods's birthday party at a local resort in Florida.(Photo by Kevin C. Cox/Getty Images) ‘Put Some Black In Their Bloodline’: Tiger Woods’ Romance with Vanessa Trump Has Fans Saying He’s Mixing Things Up in the Family Tree The mother-daughter duo were styled to perfection as they attended Woods’ 50th birthday bash at the luxury resort The Breakers in Palm Beach, Florida on January 14. Vanessa opted for a black satin gown that hit mid-calf and featured a lace-up detail running down the back, pairing the look with bold red pumps. Her 18-year-old daughter Kai, whom she shares with ex-husband, Donald Trump Jr., coordinated in satin as well, stepping out in a bright red, ankle-length gown with an open back and a front cutout, finished with black heels. Kai also sported a cast on her arm after having surgery on her wrist weeks back. According to Front Office Sports, guests were asked to wear a “touch of red” to the event. It’s a nod to the color Woods wears in his final rounds of golf tournaments and his Sun Day Red apparel brand. Despite the dress code, he reportedly only wore a black tuxedo. The celebration marked more than just his birthday, also honoring 30 years of the TGR Foundation and its work supporting education and career training opportunities for disadvantaged youth. Kai supported Woods even further by posting pictures from the party with a caption about his foundation’s education initiative. She wrote, “I recently visited one of TGR’s Learning Labs where kids are given a space to grow and further their education beyond the classroom. I love seeing organizations that are actually putting in the work to create pathways for kids to learn, build confidence, and chase their goals! Link in bio to donate.” Tiger Woods’ girlfriend Vanessa Trump and her daughter Kai stepped out in style for tonight’s RED Legacy event in Palm Beach Gardens, celebrating 30 years of the Woods Foundation and Tiger’s 50th birthday, with 300 guests expected to attend. pic.twitter.com/r0VXDRvH1t— Ways To Golf (@WaysToGolf) January 15, 2026 Her posts included a solo shot of herself and another picture of Kai and her mom smiling side by side. On Page Six fans reacted to the ladies’ glammed-up looks at the party. Vanessa Trump looks great…but also totally different. What’s going on? "Does Vanessa have some black in her? One person who saw photos of them said, “Vanessa looks younger than Kai...good cosmetic work,” and another complimented them with “Mom and daughter almost look like sisters.” A third person mentioning Donald Jr. wrote, “Vanessa is looking hottt!! I betcha Donnie Jr regrets giving her the heav-ho.” Another person suggested Vanessa only got with him for his money, writing, “What did that woman see in Don Jr. before his father ran for office? $?” Trump met her ex-husband Donald Jr. in 2003 at a fashion show when his father, President Donald Trump, introduced them. By 2004 they were engaged and married the next year. In 2007 they welcomed Kai, and, in the following years, they had four more children: Donald John Trump III, 16, Tristan Milos Trump, 14, Spencer Frederick Trump, 14, and Chloe Sophia Trump, 11. By 2018, Vanessa filed for divorce. Donald Jr. began dating the current U.S. ambassador to Greece, Kimberly Guilfoyle, that same year. They got engaged in 2020 but called it quits in 2024. View this post on Instagram A post shared by ExtraTV (@extratv) Now he is engaged to socialite Bettina Anderson whom he was first photographed with in August 2024. View this post on Instagram A post shared by Tiger Woods (@tigerwoods) Vanessa and Woods’ relationship was kept quiet throughout 2024 before they confirmed their romance in March 2025. Woods has two children, daughter Sam Alexis Woods, 18, and his son Charlie Woods, 16, whom he welcomed with his ex-wife Elin Nordegren. Like Kai, Charlie also is a talented golfer, competing in junior tournaments at the national level.
