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Sean "Diddy" Combs Verdict: 50 Cent, Aubrey O'Day and More React
Aubrey O’Day has fond memories of time with Donald Trump Jr.
Seven years after reports emerged that the Danity Kane member had been romantically involved with President Donald Trump’s oldest son between 2011 and 2012—which Don Jr. never confirmed—she made rare comments on the relationship.
“Don Jr. made me feel the most beautiful,” Aubrey told US Weekly in an interview published July 16. “He made me feel the smartest and the most beautiful, but he loved my mind more than anything else, and that’s what I love about me. The way that we loved was we loved the same.”
E! News has reached out to Don Jr.’s reps regarding Aubrey’s latest remarks about their alleged romance but has not yet heard back.
Although her dalliance with Don Jr. wasn’t the only star whose romance she gave insight into. Indeed, Aubrey admitted that her other ex, Jersey Shore’s Pauly D, whom she dated from 2016 to 2018, did not give her “any confidence,” adding, “That was probably the lowest I had ever felt, and that’s why I stayed obedient for so long.”
And while Don Jr. has never spoken publicly about Aubrey, it was reported around his 2018 divorce from Vanessa Trump the pair engaged in an extramarital relationship after meeting on The Celebrity Apprentice in 2011.
However, the Don. Jr. and Vanessa—who share kids Kai, 18, Donald III, 16, Tristan, 13, Spencer, 12, and Chloe, 11—did not address an affair when they announced their split in March 2018.
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"After 12 years of marriage, we have decided to go our separate ways,” the couple said in a joint statement at the time. “We will always have tremendous respect for each other and our families. We have five beautiful children together and they remain our top priority. We ask for your privacy during this time.”
In the years since, however, Aubrey has continued to make sly references to the alleged relationship—even alleging that Michael Cohen, a former attorney for President Trump who served time in prison for tax evasion between 2019 and 2021, had helped bury the story.
“When the Trump, Don Jr. thing got leaked in the media,” Aubrey recalled on Sofia with an F last year. “I mean, I spent likely a decade or something, maybe a little less than that, covering it up with Michael Cohen.”
Don Jr., for his part, went on to get engaged to Kimberly Guilfoyle in 2020, before the couple called it off four years later. Earlier this year, he began publicly dating Bettina Anderson.
As for Vanessa? She recently went Instagram official with Tiger Woods.
"Love is in the air and life is better with you by my side!" Tiger wrote in a March Instagram post, following reports the pair were privately seeing each other. “We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts."
Keep reading for a deeper look at the love lives of the Trump family…
SAUL LOEB/AFP via Getty Images
Donald 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.
Donald 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 Images
Ivanka 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 Images
Eric 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 Trump
Tiffany 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 Images
Barron 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 Images
Vanessa 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."
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