The Trump family has often portrayed itself as a typical, hardworking family with strong values, but a deeper look into their personal lives paints a very different picture. Donald Trump’s three marriages, his affair with a porn star, and his conviction related to sexual abuse liability tell a much more complicated story than the idealized version they’ve promoted. His son, Donald Trump Jr., seems to have followed in his father’s footsteps, showing similar behavior patterns.
Donald Trump Jr., a father of five, has experienced his own relationship struggles, including a failed marriage, a broken engagement, and a new romance. In 2018, during the hearings for Brett M. Kavanaugh’s Supreme Court nomination, Trump Jr. seemed more concerned about his sons being falsely accused of sexual assault than he did about the real issue — his daughter’s possible experience with such abuse. When asked who he was most worried about, he directly pointed to his sons.
Donald Trump Jr.’s ex-wife Vanessa Trump’s kids
Trump Jr. has five children with his ex-wife Vanessa Trump, who is 47 years old. The couple’s relationship had a somewhat awkward beginning, with Donald Trump Sr. introducing them twice at a fashion show in 2003. However, they eventually hit it off at a party. Donald Jr. proposed in front of the paparazzi at a jewelry store, offering a $100,000 engagement ring. The two were married on November 12, 2005, at Mar-a-Lago, with Donald Sr.’s sister, Judge Maryanne Trump Barry, officiating.
Vanessa is the daughter of Charles and Bonnie Kay Haydon and was raised on the Upper West Side of New York. She’s of Danish and Swedish descent and worked as a model, standing tall enough to make a good impression on designers — and her father-in-law, who had an affinity for tall women. She was considered a suitable match for the Trump family for this very reason.
The couple’s first child, Kai, was born on May 12, 2007, and is the first grandchild of Donald Trump. Now 17, Kai enjoys golfing and skiing and seems to have a close bond with her father. She even spoke at the Republican National Convention in 2024. Their second child, Donald Trump III, born February 18, 2009, is 15 and enjoys hunting with his father and brothers. Tristan Milos Trump, 13, loves fishing and is a fan of the Tampa Bay Buccaneers. Spencer, the youngest son at 12, enjoys spending time outdoors with his family. Finally, their 10-year-old daughter, Chloe, shares her older sister’s love for golf.
In 2018, Donald and Vanessa’s marriage ended, with Vanessa filing for an uncontested divorce. While the couple never publicly stated the reason for the split, it’s easy to speculate that the pressures of living in the spotlight during Trump’s presidential campaign and early years of his presidency played a significant role. Additionally, Donald Trump Jr. had been involved in some controversial situations, including a 2016 meeting with Russian lawyer Natalia Veselnitskaya, which raised suspicions about Russian interference in the election. He was also linked to rumors of an affair with pop star Aubrey O’Day in 2011.
A month before their separation, Vanessa received a mysterious envelope containing a white substance. Though it turned out to be harmless cornstarch, the incident prompted her to seek medical attention. The sender, Daniel Frisiello, was later sentenced to five years of probation for his actions.
Since the divorce, both Vanessa and Donald Jr. have moved on romantically. In 2020, Donald Jr. proposed to Kimberly Guilfoyle, a former Fox News host, but the couple never married, and it seems their engagement has ended, though neither has confirmed the breakup. Donald Jr. is now rumored to be dating socialite Bettina Anderson, with the two spotted holding hands in public. Meanwhile, Guilfoyle was appointed by her former fiancé’s father as Ambassador to Greece.
As for Vanessa, she reportedly started dating a Secret Service agent after her divorce. This no longer posed a conflict of interest, as she was no longer one of their protectees.