A former girlfriend of Donald Trump Jr. says the conservative firebrand might as well have been Prince Charming for how he made her feel.
‘Don Jr. made me feel the most beautiful,’ Aubrey O’Day, 41, told Us Weekly of President Donald J. Trump’s namesake and eldest child.
O’Day, who worked with Donald Trump Jr. on The Celebrity Apprentice in 2011, spoke with the outlet Wednesday about her past relationship with the eldest child of the U.S. president.
O’Day said that the real estate heir made her feel like ‘the smartest and the most beautiful’ person – and especially connected with her through her intellect.
‘He loved my mind more than anything else and that’s what I love about me,’ O’Day said. ‘The way that we loved was we loved the same.’
The pair was involved in a romance from the end of 2011 until the spring of 2012, during a timeframe when Trump Jr. was wed to ex-wife Vanessa Trump.


Aubrey O’Day, 41, a former girlfriend of Donald Trump Jr., 47, says the conservative firebrand might as well have been Prince Charming for how he made her feel
The fling ended when Trump Jr.’s wife at the time, Vanessa Trump, caught her then-husband cheating on her, in reading the emails he exchanged with O’Day.
Ultimately, Trump Jr.’s infidelity was a death knell for the marriage, as Vanessa, 47, filed for divorce in 2018.
Vanessa has been romantically linked to Tiger Woods in recent months.
O’Day said that not all of her celebrity exes have made her feel like a star.
She named Jersey Shore personality Pauly D as a partner who ‘did not give [her] any confidence’ during their time as a couple.
Pauly D ‘definitely brought [her] down all the time and made sure that I didn’t have like high self-worth, because [she thinks] he feared I wouldn’t stay if I did,’ O’Day said of the MTV personality, who she dated in 2016 and 2017.
She added, ‘That was probably the lowest I had ever felt and that’s why I stayed obedient for so long.’
Pauly D, 45, did not appear to have fond memories while looking back on it with Page Six seven years back.
The reality TV personality told the outlet he felt a sense of relief he and O’Day parted ways before things got too serious.

O’Day was pictured filming the NBC series The Celebrity Apprentice in October 2011 in NYC
![O'Day named Jersey Shore personality Pauly D as a partner who 'did not give [her] any confidence' during their time as a couple. Pictured in LA in 2016](https://i.dailymail.co.uk/1s/2025/07/17/00/100380101-14912765-image-a-25_1752706919751.jpg)
O’Day named Jersey Shore personality Pauly D as a partner who ‘did not give [her] any confidence’ during their time as a couple. Pictured in LA in 2016
‘The way I feel is I dodged a bullet. I’m glad that I was out of that whole situation,’ Pauly D explained.
He noted that while it took place years before, O’Day never told him about her romance with Trump Jr.
‘I found out when the world found out, it was in the press and I said, “Oh, wow! That’s crazy.” Hey listen, she did what she had to do at the time, I guess.’
For his part, Donald Trump Jr. has never publicly acknowledged the affair with O’Day amid his marriage to Vanessa, who he split from in 2018.
The former couple are parents to five children: Kai, 18, Donald III, 16, Tristan, 13, Spencer, 12, and Chloe, 11.

Trump Jr. seen on The Apprentice in 2011 with father Donald Trump and sister Ivanka Trump
O’Day can currently been seen on the E! series Botched Presents: Plastic Surgery Rewind, which is hosted by Michelle Visage and also features Kim Zolciak and Larissa Santos Lima.
According to the network, O’Day on the show ‘wants to reconsider her facial filler at the Rewind Retreat while connecting with the other participants on their shared experiences. ‘
O’Day opened up on going without makeup on the latest episode of the show, which aired Wednesday.
‘I love myself without makeup,’ O’Day said. ‘I love putting on makeup too. I think people probably would think I fear [not wearing makeup] more than I do just because I’m such a visual person and promote art that’s very, like, made up. But I’m just like any other girl. I like it to come off at the end of the day.’