Long before Kimberly Guilfoyle, Donald Trump Jr. found himself in an alleged affair with
reality TV star, Aubrey O'Day.
And even though this rumored fling is very much in the rearview, let's examine all the
gossip anyway.
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 on-show "adviser."
O'Day even admitted on-screen that she was crushing –
“Don Jr. makes me nervous, because I have a very big crush on him and I don’t want
to disappoint him.”
– but Trump Jr.'s wife, Vanessa, was reportedly pregnant with the pair's third child, so theoretically,
that'd make him off-limits.
“I’d like to be part of your family.”
“OK, well that would be very…”
“He’s married already.”
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, quote, "floating on clouds”
after an anonymous lover sent her "wall to wall" flowers.
Those probably weren't cheap.
Us Weekly claims the pair's late 2011 affair lasted until March 2012.
Not long after, O'Day confirmed in a tweet that an unnamed someone, quote, made "a move"
on her during Celebrity Apprentice.
Aubrey O'Day has had her fair share of scandals, like that time she allegedly dyed her dogs’
fur.
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, quote, "pursued"
the reality star.
O'Day actually believed, we’re told, that his marriage was over.
Why would she think that?
Well, that's apparently what he told her.
To be fair, the source also told the tabloid that the marriage did seem, quote, "over long
before Aubrey came along."
It just happened to not actually be over.
Us Weekly claims that O’Day thought that she and Trump would end up together, and still
hasn’t forgotten about the connection even nearly a decade after it allegedly occurred.
O’Day told Variety in 2019:
"We were each other's soulmates.
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."
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, within the dates of the pair’s alleged involvement,
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 seems 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 apparently still holding out hope.
Though she appeared to have a brief lapse when she got emotional while listening to
Adele’s 21, 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,
quote, "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 rendezvous in various American cities, all the while penning passionate
love notes.
Let's just hope Don's love letters aren't anything like his Twitter feed.
He sure has a way with words.
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 threatened to walk out of Don Jr.’s life
after finding out about O'Day, another claimed she was, quote, "devastated" when Don admitted
he was planning to make a new life with 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,
quote, "shame" her "away from her husband."
The confrontation apparently took place over the phone.
Just like Romeo and Juliet, these star-crossed lovers did not get their family's approval,
and that's what allegedly led to the demise of their relationship.
According to Us Weekly, the Trumps, quote, "pressured" Donald Jr. to "end it with Aubrey"
after the emails were uncovered.
In fact, Page Six reports that the businessman's father — himself not an amateur when it
comes to fuzzy marriage boundaries — stepped in and told his son to, quote, "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 that:
"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 in 2018.
The pair ended up having a couple more kids before this, however, with their fifth child
born in June 2014.
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.
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
same man who inspired the album as a whole.
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?"
The man replies:
"I couldn't do what I said I would do."
“And, um…
Be careful about dating men with the last name ‘Trump’.”
It may have taken a while, but eventually Aubrey O'Day entered a brand new relationship
with none other than Jersey Shore star DJ Pauly D. According to Us Weekly, the reality
stars met on the set of a reality show: E!'s Famously Single.
They started dating in February 2016.
Like you'd expect from two people who appeared on a show called Famously Single, the couple
didn’t make it down the aisle.
E! reports that Pauly D ended things because the singer was pressuring him to tie the knot.
She previously told the magazine that she, quote, "wanted a ring, like, ASAP," which
might have cramped the DJ's Las Vegas lifestyle.
“Between you and I, like…”
“You’re falling in love with me?”
“No.
Like…”
“You’re falling in love with me?”
“Between you and I, like I’m…”
“You’re falling in love with me?”
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, telling Us Weekly
that he, quote, "tortured" her in their relationship.
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, quote, "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, quote, "interviewing divorce lawyers" before Trump took office,
and had it not been for the presidency, the pair might have split a whole lot sooner.
At the time of this video, 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.
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., quote, "hates his father" and disdains his younger
brother Barron.
The singer also made intimate claims about Ivanka Trump’s romantic preferences, and
about brother Eric Trump’s involvement with a woman who was not his wife.
Of course, no one can confirm or deny this sort of rumor, but with O’Day, we expect
that the hot goss will just keep flowing.
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 another 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, quote,
"about pulling a muscle changing a tampon."
In the DM, he joked about not, quote, "asking for pics from your bathroom tweet."
Yikes.
Trump Jr.'s team wrote the whole thing off as a joke, but Stetten 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 isn’t the same thing as an actual affair, but it's
still not a great look for a married man.
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 controversial public figure.
Per Elle's timeline, the pair were first romantically linked the month after Trump Jr. announced
his divorce.
From there on, she became a perennial issue for the Trumps, according to Politico.
She allegedly, quote, "frequently joked about her sex life" with Don Jr. and even went as
far as offering, quote, "a lap dance to the donor who gave the most money" at a campaign
fundraiser.
The couple's banter was reportedly TMI, and certain donors were said to have been spooked.
All in all, though, Guilfoyle appears to fit right into the Trump universe.
And at the time of this video, the Trump-Guilfoyle power couple may 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.
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