Inside Aubrey O'Day's Alleged Affair With Donald Trump Jr.

Donald Trump didn't so much spend his presidency building a wall as he did tearing one down — the wall that separated Hollywood and Washington DC. In some regards, Arnold Schwarzenegger walked with his stint as California governor so that the former Apprentice host could fly (privately and on Air Force One). This is, perhaps, the only explanation as to why Aubrey O'Day, former Danity Kane singer-turned-career-reality-star, could possibly get wrapped up in a political scandal. This time, the scandal didn't involve the former president, but rather his eldest son, Donald Trump Jr

Long before Kim Guilfoyle cosplayed The Hunger Games at the Republican National Convention, Trump Jr. and O'Day reportedly fell into a passionate romance akin to Romeo and Juliet — if Romeo happened to be a married father nearing middle age. It took years for the so-called truth to unfold, starting from the moment on election night in 2016 when O'Day ominously tweeted and deleted (via Us Weekly), "My story I didn't tell is worth millions now." By 2018, that story she didn't tell became a story someone else told to Page Six. Thus, the affair was cemented in the history books somewhere between Covfefe and the former president's alleged diet coke button. 

Here's the lowdown on the scandalous alleged affair between Donald Trump Jr. and Aubrey O'Day. Never mind the cheesecake, P. Diddy should have taught the singer how to navigate this one on Making The Band!

They reportedly met on the set of The Celebrity Apprentice

Since first appearing on Making the Band 3 in 2005, Aubrey O'Day's reality TV career has run the full gamut. We saw her fall in love on Famously Single, struggle in her relationship on Marriage Boot Camp, and work through her breakup on Ex on the Beach. Basically, she's done it all — including The Celebrity Apprentice, where she met her future alleged lover Donald Trump Jr.

According to Page Six, it all started towards the end of 2011 when O'Day was a contestant on Season 5 and Trump Jr. was an "adviser." The pair just happened to work together on a project themed around Adam and Eve's forbidden fruit (perhaps they had forbidden things on the brain?). O'Day even admitted on-screen that she was crushing, but Trump Jr.'s wife was reportedly pregnant with the pair's third child, so theoretically, that'd make him off-limits. Either way, Buzzfeed, who combed through O'Day's social media posts from around that time, found a November 2011 tweet where the reality star mentioned "floating on clouds” after an anonymous lover sent her "wall to wall" flowers. Those probably weren't cheap.

Us Weekly claims the pair's affair lasted all the way until March 2012. Not long after, O'Day confirmed in a tweet (via Buzzfeed) that someone — an anonymous someone — made "a move" on her during Celebrity Apprentice.

Aubrey O'Day believed Donald Trump Jr.'s marriage was over

Aubrey O'Day has had her fair share of scandals, like that time she allegedly dyed her dog's hair (girl, are you good?). This time, the singer wasn't actually chasing the drama — the drama was chasing her. A source that spoke to Page Six claimed that Donald Trump Jr. was the one who "pursued" the reality star. O'Day actually believed that his marriage was over. Why would she think that? That's apparently what he told her.

To be fair, the source also told the tabloid that the marriage did seem "over long before Aubrey came along." It just happened to not actually be over. Nonetheless, Us Weekly reports that the couple was "very serious all of a sudden," and O'Day "thought they were going to be together for real." The reality star still maintains the fact that they were "soulmates," a whopping eight years after she became his mistress.

"We were each other's soulmates," she told Variety in 2019. "I believe soulmates are forever, so yes. But I believe you can have multiple soulmates. At the time, him and I were soulmates. I can only speak for myself, but I didn't break up a marriage and I wasn't involved in stealing anyone from their [spouse] and all that nonsense. It's up to them to discuss what marriage is for them, at that level of power, success and money. It's completely different to the way we understand marriage."

Aubrey O'Day had her doubts

Just because Aubrey O'Day thought Don Jr. was her soulmate doesn't mean that she never had any doubts. Buzzfeed uncovered a tweet from December 2011 where the reality star ominously posted a select set of 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 ..." That looks like a subtweet if we ever saw one.

As we know from the classic trope, the husband never leaves his wife for his mistress. Nonetheless, O'Day was still holding out hope. Though she appeared to have a brief lapse when she got emotional while listening to 21 (a right of passage for all 20-somethings and Adele stans), it was business as usual by Christmas. Per Buzzfeed, the star was tweeting and Instagramming a loved-up storm, claiming her "babe" made her a "magical" Christmas tree; posting pictures of her lover's feet; hanging out at "the Trump" (which is presumably Trump International Hotel), and blasting out images from vacations and "romantic getaways." Don't forget all the "#sex." Yes, that's a real hashtag she actually used.

O'Day's posts more or less align with the story insiders told Page Six. The pair would reportedly "meet up in various cities during their fling and [write] each other love notes." Let's just hope Don's love letters aren't anything like his Twitter feed. He sure has a way with words.

But her emails!

Emails are a hot topic in the Trump household, and they're allegedly how Donald Trump Jr. was caught red-handed. If only he had used a more secure server — or even just Snapchat, the base-level standard for cheaters trying to cover their tracks. According to Us Weekly, Vanessa Trump discovered her husband's months-long affair by uncovering a so-called "treasure trove" of incriminating emails.

What happened next is a little up in the air. Though one source told Page Six that Vanessa "was going to leave" after finding out about O'Day, another claimed she was "devastated" when Don admitted he was planning "to leave her" for his mistress. That's where things get ultra-dramatic.

According to Us Weekly, the mother of five actually confronted O'Day in an attempt to "shame" her "away from her husband." A source told the tabloid, "She called Aubrey with her kids on the phone." A separate source revealed, "Vanessa went crazy and was super jealous." As painful as it is to watch two women fight over a dude who looks like a villain from an '80s cartoon, Vanessa did take a vow. Until death — or adultery — do them part.

The Trump family shut down Donald Jr.'s affair

Just like Romeo and Juliet, these star-crossed lovers did not get their family's approval, and that's what led to the demise of their relationship. According to Us Weekly, the Trumps "pressured" Donald Jr. to "end it with Aubrey" after the emails were uncovered. In fact, Page Six reports that the businessman's father — who could arguably be considered the authority on cheating and getting caught — stepped right in and told his son to "knock it off" as soon as he learned about the affair.

This story appears to be reflected in a series of subtweets from O'Day. As Buzzfeed points out, in May 2012, the singer tweeted, "a man will always desire his father's approval even if he despises him." Not long after, she tweeted, "I hope u still stalk my tweets and remember how much u loved me, and hate how weak you were to not fight for us."

Don Jr. didn't appear to fight for O'Day because he never ended up leaving his wife, at least not until she filed for divorce years later. The pair ended up having a couple more kids, announcing their fifth child in 2014.

Aubrey O'Day's breakup song 'DJT' wasn't obvious at all

Five years before Aubrey O'Day's alleged affair went public, the singer released her album Between Two Evils with a curious breakup track called "DJT." In case you're wondering what those letters stand for — slow down. The singer has never confirmed or denied anything, but John does happen to be Donald Trump Jr.'s middle name. In other words, he probably owns some cufflinks somewhere that say DJT. Really though, the letters could stand for anything, like "diamond jewelry, thanks" or "dirty Jeep Trailhawk," but we're guessing it's got something to do with the alleged affair.

O'Day knows how to feed the drama. She wouldn't be a career reality star, otherwise. As Buzzfeed points out, she did confirm to a fan that the track's title referred to the "man [she] wrote the album about." The verses, which are a spoken word phone conversation between ex-lovers, certainly point to a relationship that may echo her own. It's particularly evident when she asks, "And you want to go back and live in the life that you had ... forever?" and the man replies, "I couldn't do what I said I would do."

Surely, Don Jr. never told O'Day that he'd leave his wife and then ... didn't.

From DJT to DJ Pauly D

It may have taken a while, but eventually, the cabs showed up to chauffeur Aubrey O'Day into a brand new relationship with none other than Jersey Shore star DJ Pauly D. Nothing mends a broken heart like a GTL (gym, tan, laundry for those who've never spiraled in Seaside Heights). According to Us Weekly, the reality stars met on the set of a reality show. Who would've thought? Both of them appeared on E!'s Famously Single and started dating in February 2016.

Like you'd expect from two people who appeared on a show called Famously Single, the couple fell just short of marriage. E! reports that Pauly D ended things because the singer was pressuring him to tie the knot. She previously told the magazine that she "wanted a ring, like, ASAP," which might have cramped the DJ's Las Vegas lifestyle, but he's a father now, right?

Still, by reality TV standards, Pauly D and O'Day's bizarre relationship lasted an eternity. In real life, that translates to roughly a year and a half, and the whole demise played out across episodes of Marriage Boot Camp: Reality Stars and the tabloids. At one point on the show, O'Day went as far as wishing death on Pauly D, who she told Us Weekly "tortured" her in their relationship. At the time of this writing, O'Day still appears to be famously single.

It took years, but Vanessa Trump finally filed for divorce

Though Donald Trump Jr. and Vanessa Trump had two more children since his alleged affair, their marriage did not last. The same month that rumors of the affair broke in the tabloids, Vanessa filed for divorce. A source told People that they had already "been living separate lives," and from the looks of it, the affair was the least of their problems.

According to Page Six, the couple had issues way before O'Day was in the picture, stemming all the way back to before their 2005 wedding. Vanessa was allegedly "interviewing divorce lawyers" before Trump took office, and had it not been for the presidency, the pair might have split a whole lot sooner.

The primary reason for the breakup appears to be money — mainly that Trump Jr. is allegedly "cheap" despite his father's multi-billion-dollar legacy and treated Vanessa "like a second-class citizen." A source told the tabloid, "He gives her very little help and has been keeping her on a tight budget. She doesn't live a lavish life and can very rarely pick up a check at dinner." She reportedly even had to ask her mom for financial help. Of course, Vanessa's camp denied the claims, and their divorce was finalized in February 2019, anyway. If Trump Jr. really did things like take away half of their daughter's Halloween candy because "it's never to [sic] early to teach her about socialism," it's hard to blame her.

Aubrey O'Day spilled the tea during the presidential debate

At the time of this writing, it's been almost a decade since O'Day allegedly had her affair with Donald Trump Jr. Nonetheless, he still appears to be living in her mind rent-free. C'mon, if the Secret Service reportedly has to pay for their rooms at Mar-a-Lago, O'Day should at least charge something. It turns out that "DJT" might just be paying with his dignity because O'Day has no problems running her mouth about the whole Trump gang.

In October 2020, the former Danity Kane singer was like most of us watching the final presidential debate — hate-tweeting up a storm and then deleting it when the pangs of anger subsided. According to Newsweek, she dished some very salacious details about her alleged ex and his siblings. This included claims that Don Jr. "hates his father" and thinks his youngest brother Barron is a "little s*** a***."

"... They were on the private jet and Barron didn't like his food, so he threw the plate across the plane at the attendant," she tweeted (via Newsweek). "NONE of these people are INNOCENT of being a******* & liars!"

The singer also claimed that Ivanka Trump "is a lesbian on the low" and that Eric Trump "f***** Miss Universe on The Apprentice boardroom table while with his now-wife." Maybe having affairs with women from The Apprentice runs in the family. Is it a matter of nature vs. nurture?

By the way, Aubrey O'Day may have not been the only one

The media has largely been singling out Aubrey O'Day as Donald Trump Jr.'s mistress, probably because she's so vocal about it and has such a massive presence with her sprawling reality TV career. The truth is that she may not actually be the only one. There's a world in which O'Day was two-timed, and Vanessa was three-timed.

According to People, the former president's son and sometimes Twitter troll spent his free time in late 2011 sliding into a model's DMs. Let's not forget that around the same time, he started a relationship with O'Day and Vanessa Trump had just given birth. You'd think he'd be a little busy, but we digress.

Model Melissa Stetten spilled the alleged beans on Twitter when she posted a screenshot of a private conversation with the businessman, who replied to a joke she tweeted "about pulling a muscle changing a tampon." In the DM, he joked about not "asking 4pics from ur bathroom tweet." Trump Jr.'s team wrote the whole thing off as a joke, but Statten claimed she didn't even know the businessman before he tweeted at her and joked about intimate photos. The pair also shared a flirty exchange in public, but it looks like it didn't go further than that. We can all probably agree that flirting pales in comparison to an actual affair, but it's still not a great look for a married man.

Donald Trump Jr. settled down with Kimberly Guilfoyle

Donald Trump Jr. eventually moved on from both Aubrey O'Day and Vanessa Trump. It actually seems like he's found his perfect match with former Fox News host Kimberly Guilfoyle, an equally as controversial public figure who, according to The New Yorker, has been accused of sexual harassment and reportedly uses inappropriate language at political events.

Per Elle's timeline, the pair were first romantically linked the month after Trump Jr. announced his divorce. From there on out, she became a long-standing "HR nightmare" for the Trumps, according to Politico. She allegedly "frequently joked about her sex life" with Don Jr. and even went as far as offering "a lap dance to the donor who gave the most money" at a campaign fundraiser. The couple's "sexually suggestive" banter reportedly "made some donors uncomfortable."

All in all, Guilfoyle appears to be right at home with President Grab 'Em By The P***y and his eldest son, who's preferred pastime is murdering rare and endangered animals. Actually, they may literally be house-hunting. According to The New York Post, the couple was spotted shopping for homes in Florida, where they'll presumably join Don Jr.'s father and the rest of his siblings.