Ivanka Trump’s connection to Vanessa Trump has withstood kids, divorce and even new romances.
In March 2025, Tiger Woods surprised followers after confirming he was dating Donald Trump Jr.’s ex-wife, Vanessa.
“Love is in the air and life is better with you by my side!” the golfer wrote via Instagram at the time. “We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts.”
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While friends and fans were quick to send well wishes to the athlete, some were quick to notice Ivanka’s comment on the photo post.
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“So happy for you both ! 
,” she wrote in the comments section after Vanessa’s daughter, Kai, reportedly liked the post.
While it’s unclear when Vanessa and Ivanka’s friendship began, President Donald Trump was responsible for initially connecting his eldest son with Vanessa all the way back at a 2003 event.
“I’m at this fashion show,” Vanessa recalled to The New York Times in 2006. “Donald Trump comes up to me with his son: ‘Hi, I’m Donald Trump. I wanted to introduce you to my son Donald Trump Jr.’”
It wasn’t until the pair attended a birthday party at a New York City restaurant where they ended up hitting it off. Vanessa and Donald Jr. married in 2005 at Mar-a-Lago in Palm Beach, Florida, where Ivanka reportedly served as a bridesmaid.
Although Vanessa and Donald Jr’s marriage came to an end when they filed for divorce in 2018 after 13 years of marriage, Ivanka was still photographed at major events with her former sister-in-law, including the Republican National Convention in 2016 and the 2017 inauguration for Ivanka’s father.
Before Donald became president, Ivanka had a successful fashion brand while Vanessa released her own line of handbags called La Poshett.
The duo also each appeared on The Apprentice to serve as the eyes and ears for Donald as he searched for a winner.
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Away from the spotlight, the pair are also mothers and raising kids under the spotlight.
During their marriage, Vanessa and Donald Jr. welcomed five kids including Kai, Donald III, Tristan, Spencer and Chloe. As for Ivanka, she shares Arabella, Joseph and Theodore with husband Jared Kushner.
Both moms continue to celebrate big milestones in their children’s lives on social media. Vanessa recently celebrated daughter Kai’s new job on the golf course while Ivanka cheered on Theodore at his first flag football tournament.
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