Originally appeared on E! Online

Love is in the fairway.

Rachel Uchitel, who made headlines in 2009 as one of then-married Tiger Woods’ mistresses, recently announced her engagement to security businessman Dan Donovan.

In a March 28 Instagram post featuring pictures of the beachside proposal and massive emerald-cut diamond, Rachel wrote, “So this happened #engaged.”

For his part, Dan shared another photo from the engagement to Instagram, writing atop the pic, “She brings me to my knee.” He also captioned the post, “Something shiny for the most amazing woman.”

While Rachel and Dan were all smiles about their engagement, they aren’t the only couple who have recently announced they’re taking a swing at love. Five days before the Miss Understood with Rachel Uchitel podcast host’s news, Tiger confirmed his new relationship with Vanessa Trump, who shares kids Kai, 17, Donald III, 16, Tristan, 13, Spencer, 12, and Chloe, 10, with ex-husband Donald Trump, Jr.

“Love is in the air and life is better with you by my side!” the golfer wrote on his Instagram March 23, which included a picture of the pair 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.”

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At the time, Vanessa re-shared the post to her personal Instagram Story.

Multiple outlets reported that Tiger—who shares kids Sam, 17, and Charlie, 16, with ex-wife Elin Nordegren—and Vanessa have been dating for several months and that the Trump family has been supportive of the relationship.

In fact, President Donald Trump had recently hosted the athlete at The White House for a Black History Month event in February and celebrated him as “one of the greatest golfers in the world.”

Rachel Uchitel, Tiger Woods

Instagram/Rachel Uchitel; Hugo Philpott/UPI/Shutterstock

Plus, the Apprentice alum had previously bestowed Tiger with a Presidential Medal of Freedom during his first presidential term in 2019.

“We are in the presence of a true legend—an extraordinary athlete who has transformed golf and achieved new levels of dominance,” the president said at the time. “He’s also a great person.”

Read on for a deeper dive into the love lives of the Trump family.

Donald Trump

<p>Donald Trump</p>

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.

Donald Trump Jr.

<p>Donald Trump Jr.&nbsp;</p>

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.

Ivanka Trump

<p>Ivanka Trump</p>

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.

Eric Trump

<p>Eric Trump</p>

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.

Tiffany Trump

<p>Tiffany Trump</p>

Barron Trump

<p>Barron Trump</p>

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.”

Vanessa Trump

<p>Vanessa Trump</p>

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.”

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