Donald Trump Jr. remains a popular name in the MAGA circle. Republican supporters often view him as an authentic, charismatic and honest political figure, whereas critics argue that he is often aggressive and biased when it comes to his father, Donald Trump’s public confrontations and political ideas.
Don Jr. also helps run the Trump Organization with his younger brother Eric. Beyond politics and business, Trump Jr.’s personal life has frequently attracted just as much public attention.
In 2005, Donald Trump Jr. married model Vanessa Haydon at his father’s Mar-a-Lago home, yet not many people knew he reportedly got involved in a tabloid scandal with singer and reality TV star Aubrey O’Day.
Donald Trump Jr. reportedly had an affair with Danity Kane alum Aubrey O’Day after she appeared on “Celebrity Apprentice” in 2011 https://t.co/473eSXvvcb pic.twitter.com/eHyVtbaIZZ
— New York Daily News (@NYDailyNews) March 19, 2018
The alleged affair, which reportedly occurred in 2011 and 2012, did not become public until years later. The well-known TV personality met Trump Jr. while competing on Season 5 of “The Celebrity Apprentice” in 2011, where he served as an adviser while his father hosted the show.
Sparks flew between the two while working together. Vanessa was pregnant with their third child at the time, but the affair still continued. According to Nicki Swift ‘the couple reportedly met in various cities and exchanged love notes.’
Buzzfeed also stumbled upon a tweet from December 2011, where Aubrey O’Day selected lyrics from “He Won’t Go” by Adele: ‘Will he still love me when he’s free? or will he go back to the place where he will choose the poison over me ‘
Us Weekly reported that the alleged affair lasted several months and ended in March 2012. When news of the affair became public in 2018, Vanessa Trump reportedly discovered emails and texts between her husband and Aubrey O’Day.
Vanessa Trump Discovered ‘Sexy Texts’ from Aubrey O’Day While Donald Jr. Showered: Source https://t.co/YhVPWIeGEx
— People (@people) March 21, 2018
An insider source claimed, “Vanessa went crazy and was super jealous.” Another added, “She allegedly called Aubrey with her kids on the phone.” Additional sources also said that Trump Jr. may have thought about leaving the marriage, but ended up staying.
He never promised his former girlfriend that he would leave his wife and kids. Vanessa and Don had their fifth child in 2014. They are parents to five children: Kai (18), Donald III (16), Tristan (13), Spencer (12), and Chloe (11).
In a 2019 interview with Variety, she referred to Trump Jr. as a “soulmate,” while also maintaining that she did not believe she had broken up a marriage. She suggested that she had been told the marriage was effectively over at the time.
However, Vanessa and Don stayed together until Vanessa filed for divorce in March 2018. According to E! News, while Don has never talked about Aubrey O’Day in public, several news reports say the supposed affair ruined his marriage, and infidelity and adultery were the reasons for their divorce.
“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,” their statement said.
BREAKING: @DonaldJTrumpJr’s wife Vanessa files for divorce https://t.co/OtGnmms04a pic.twitter.com/ShYkMNIxLZ
— New York Daily News (@NYDailyNews) March 15, 2018
The father of five eventually began dating Kimberly Guilfoyle, who is now the U.S. ambassador to Greece, in 2018. The couple got engaged, but they broke it off in 2024.
Before news of his breakup became public in MAGA circles, Don was allegedly seen with Palm Beach socialite Bettina Anderson.
BREAKING NEWS:
President Trump just announced at the White House that his son @DonaldJTrumpJr and his girlfriend Bettina Anderson are getting married! They just got engaged.
Congratulations to them both. pic.twitter.com/psb38nTGla
— Laura Loomer (@LauraLoomer) December 16, 2025
Currently, Don Jr and Anderson are engaged as of December 15, 2025, after he asked her to marry him in a private proposal. Don Jr. announced the engagement during a White House event.
“This has been the most unforgettable weekend. I get to marry the love of my life, and I feel like the luckiest girl in the world. Thank you.” Anderson said as applause followed.
