Tiger Woods’ ex-girlfriend engaged
Rachel Uchitel has announced her engagement. The good news comes just days after golfer Tiger Woods went public with his relationship with Vanessa Trump.
According to People, Rachel Uchitel announced her engagement to businessman Dan Donovan. The couple shared a romantic proposal moment at Rosewood Miramar Beach, California. Donovan got down on one knee and presented Uchitel with a diamond ring.
The romance began three years ago when they connected on the Bumble app but only started dating for the past 8 months. Donovan also has a close relationship with Uchitel’s daughter, Wyatt (12 years old). She was the one who helped him choose the ring.
Rachel announced the good news just days after Tiger Woods, her ex, officially confirmed his relationship with Vanessa Trump, Donald Trump’s ex-daughter-in-law.
Rachel Uchitel was involved in a Tiger Woods affair in 2009. At the time, she was a manager of a high-end nightclub and was accused of having an affair with Woods while the golfer was married. The incident made her the center of the scandal. Woods later had to publicly apologize and withdraw from the golf world for a while.
Currently, Uchitel works in the media and entertainment industry. She hosts the podcast Miss Understood, sharing about life and the dark side of fame. Uchitel also participated in the reality TV show Celebrity Rehab with Dr. Drew and appeared in the HBO documentary Tiger (2021).
Tiger Woods is a golf legend with 15 major titles, including 5 Masters championships. He was once the highest-paid athlete in the world but his career was hit by a 2009 affair scandal and injuries. However, Woods made an impressive comeback with the 2019 Masters championship.
Tiger Woods and Vanessa Trump Tee Off New Romance: Inside the Love Lives of Donald Trump’s Family
Tiger Woods confirmed he’s dating Vanessa Trump, the ex-wife of Donald Trump Jr. As for Ivanka Trump and Tiffany Trump? Read on to learn more about their love lives.
Tiger Woods and Vanessa Trump aren’t puttering around when it comes to sharing how they feel about each other.
“Love is in the air and life is better with you by my side!” the pro golfer wrote on Instagram March 23 alongside photos of the pair smiling and cuddling in a hammock. “We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts.”
Those close to their hearts include their children: Tiger shares daughter Sam, 17, and son Charlie, 16, with ex-wife Elin Nordegren while Vanessa is mom to Kai, 17, Donald III, 16, Tristan, 13, Spencer, 12, and Chloe, 10, from her former marriage to Donald Trump Jr.
And while some may be surprised by Tiger and Vanessa’s relationship, it’s actually been teeing up for some time. Not only do Charlie and Kai compete in the same golf tournament but the 15-time majors champion has been close to the Trump family for a while.
Back in 2019, during President Donald Trump‘s first term, Tiger was awarded the Medal of Freedom. And more recently, he attended a February event at the White House in honor of Black History Month.
Instagram / Tiger WoodsTiger and Vanessa’s relationship also has the stamp of approval from her former sister-in-law Ivanka Trump. After all, she commented on their Instagram hard launch, “So happy for you both.”
And the Trump family is so happy about how their family is growing. While Ivanka already has three kids with husband Jared Kushner and her brother Eric Trump has two with wife Lara Trump, their sister Tiffany Trump is expecting the arrival of her and husband Michael Boulos‘ first baby any day now.
For a closer look inside their love lives, read on…
SAUL LOEB/AFP via Getty ImagesDonald Trump
Following marriages to Ivana Trump and Marla Maples, Donald Trump met third wife Melania Trump at a 1996 New York Fashion Week fete.
“It was a big fashion party that my friend organized, fashion week, and he invited me,” the native of Mesto, Slovenia recalled on a 2016 episode of On the Record With Greta Van Susteren. “That’s how we met with Donald.”
After marrying in a lavish 2005 wedding at his Mar-a-Lago estate in Florida, they welcomed son Barron Trump the following year.
InstagramDonald Trump Jr.
Months after ending his 13-year marriage to model Vanessa Haydon in 2018, Donald Trump Jr.—Trump’s eldest child with first wife Ivana—began dating former Fox News host Kimberly Guilfoyle.
Having known each other for years, Guifoyle said she realized instantly the father to Kai (who made a speech at the 2024 Republican National Convention) Donald III, Tristan, Spencer and Chloe was her person.
When they went on their first date, “that was it,” Guilfoyle told Metropolitan Palm Beach magazine in 2022. “Sparks. In fact, we have been together from that night on, happily ever after!”
The couple got engaged on New Year’s Eve 2020. But four years later, Don Jr. confirmed their split. He’s since been linked to Bettina Anderson.
John Shearer /Getty ImagesIvanka Trump
As Jared Kushner recalled in his book Breaking History: A White House Memoir, he was introduced to Ivanka Trump, the president’s daughter with ex Ivana, in 2007 after her father suggested they meet to discuss real estate.
“The conversation soon turned to NASCAR, New Jersey diners, and other unlikely interests that we had in common,” he wrote. “That led to a second lunch at my favorite Indian restaurant, the Tamarind Flatiron & Tea Room on Twenty-Second Street, where we talked for three hours.”
Despite a brief split, they finalized their partnership in 2009—marrying at New Jersey’s Trump National Golf Club—and welcomed daughter Arabella in 2011, followed by sons Joseph in 2013 and Theodore in 2016.
Anna Moneymaker/Getty ImagesEric Trump
When North Carolina native Lara Trump was introduced to Eric Trump, the politician’s younger son with ex-wife Ivana, she knew she was at the height of something.
“When I first met Eric, I did not know who his dad was,” she recalled on her podcast The Right View of meeting the 6-foot-5 Georgetown University grad in 2008. “I didn’t know his last name initially. I just knew I met some really tall guy out.”
Married at Mar-a-Lago in 2014, they welcomed kids Luke in 2017 and Carolina in 2019. A television producer when she started dating her future husband, Lara served as a campaign advisor for Trump in 2016 and 2020 before being elected as co-chair of the Republican National Committee in March 2024.
Instagram / Tiffany TrumpTiffany Trump
Tiffany Trump—the Apprentice alum’s only child with second wife Maples—hard launched her relationship with motorcycle heir Michael Boulos in January 2019, providing her Instagram followers with a glimpse at their shared holiday celebrations weeks earlier. Announcing their engagement two years later, the pair wed at Mar-a-Lago in November 2022, the Georgetown Law graduate labeling the experience “magical” in a social media post.
Trump revealed his daughter’s pregnancy during a Oct. 10 campaign event, telling the crowd at the Detroit Economic Club, “She’s an exceptional young woman. And she’s going to have a baby. So that’s nice.”
Eva Marie Uzcategui/Bloomberg via Getty ImagesBarron Trump
Though Barron Trump, the President’s now-adult son with third wife Melania, hasn’t publicly addressed his dating life, his father suggested the New York University student isn’t prioritizing romance at the moment.
“I’m not sure he’s there yet,” Trump said, when asked by businessman Patrick Bet-David on his PBD Podcast if the college freshman is “good with the ladies in school.”
While Trump said he didn’t believe his youngest had a girlfriend, he raved, “He’s very, very smart. He’s a good student .. goes to a great school and does really well. And he’s a very nice guy.”
Brian Rothmuller/Icon Sportswire via Getty Images; Dimitrios Kambouris/Getty ImagesVanessa Trump
Years after finalizing her divorce from Don Jr., the former model is teeing off a new romance, she and Tiger Woods made their romance Instagram official in March 2025.
As for what Vanessa’s former in-laws think of her new man, President Trump previously made it clear he’s nothing short of a big fan, with the Masters champion even attending a White House Black History Month event in February 2025. And he previously bestowed Tiger with the Presidential Medal of Freedom back in 2019.
“We are in the presence of a true legend—an extraordinary athlete who has transformed golf and achieved new levels of dominance,” Trump said at the time. “He’s also a great person.”
