Spending time with your pregnant wife is a perfectly decent way for a husband to behave
although that's not necessarily the case when you're hanging together at an infamous monument
to hedonism. But that's just one strange detail in Don Jr. and Vanessa Trump's marriage
Donald Trump Jr. and his ex-wife, Vanessa Trump, didn't exactly have a magical first encounter
when they met in 2003. According to Vanessa, it wasn't love at first sight. As she recounted to
the New York Times in 2006, I'm at this fashion show, Donald Trump comes up to me with his son
Hi, I'm Donald Trump. I wanted to introduce you to my son, Donald Trump Jr
They then struck up a short, uncomfortable conversation before the show started, only to have Donald Sr. try to reintroduce them again a second time
As Vanessa explained, Donald comes back up to me again. I don't think you've met my son, Donald Trump Jr
She then responded, Yeah, we just met, five minutes ago. Weeks later, Don Jr. and Vanessa ran into each other again, while out with mutual friends
They talked for an hour, initially not remembering their awkward first meeting until
it later dawned on them and became something to bond over. Still, Don Jr. wasn't thrilled about
his father playing matchmaker, as he admitted, it wasn't really my M.O. to have my father try to
pick up girls for me. It didn't take long for Don Jr. to pop the question to Vanessa. It might have
helped that he reportedly got his engagement ring for free, thanks to a promotional deal from the
jewelry dealer Bailey Banks and Bill. It was in November 2004 when he got down on one knee in the
Shorthills Mall in New Jersey and asked Vanessa for her hand in marriage. TV crews and paparazzi
photographers were reportedly the only ones allowed to witness the moment. Despite the arguably tacky
setting, the bride-to-be was all smiles, showing off her four-carat emerald-cut diamond sparkler
worth $100,000. A representative for the jewelry dealer declined to comment on their agreement with
Don Jr., although an insider told the New York Post, it's probably the same kind of deal his
father has with Graff. Graff has a lucrative product placement slot on The Apprentice
Donald Sr. scolded his son for the free reign decision during an interview on Larry King Live
by declaring, You have a name that is hot as a pistol. You have to be very careful with things like that
I'm very happy. She better be very happy. The road to marriage for Vanessa Trump involved getting rid of some skeletons in her closet
A childhood friend of hers once told GQ that she used to date Valentin Rivera a convicted criminal who is allegedly a member of the street gang the Latin Kings Rivera himself confirmed the rumors to Page Six
sharing dozens of letters Vanessa sent him during their five-year relationship, which began when she was 15, and continued into his prison sentence. As she wrote in one letter
dated 1993, my 18th birthday, you'll be back in my arms, my prom, and I want to get pregnant and
have a baby with you after January. Vanessa reportedly even visited Rivera at Rikers Island
while he was serving time for assault. Donald Trump Sr. reportedly found out about this chapter
in her life and arranged for a meeting to discuss it. She then reportedly assured him that their
family dynasty wouldn't be marred by any lingering gang ties. The Playboy Mansion probably isn't the
first place you'd expect to run into an expectant mother. Nevertheless, as Donald Trump Jr. revealed
in January 2007 when he was a guest on Adam Carolla's radio show, his pregnant wife tagged
along with him to Hugh Hefner's former playground, and he wasn't exactly happy about that. As he recounted
Donald Trump Jr. has a history of having a wandering eye, including public flirtations
on social media. For example, model Melissa Stettin has claimed that he exchanged private
messages with her in 2011, just a month after his wife gave birth to their third child. In 2018
Stettin tweeted, Surprised his marriage didn't work out since he was sending me DMs a month after his wife gave
birth. This happened shortly after news broke that Don Jr. and Vanessa were divorcing
Stettin shared a screenshot of a private DM from Don Jr. that was a response to her tweet about
pulling a muscle while removing a tampon, in which he wrote, While I'm getting s*** for the bacon comment, glad I opted not to send the tweet asking for
pics from your bathroom tweet last night. People need to chill. A spokesperson for Don Jr. claimed
to People magazine that the interaction was a joke, but that wasn't how Stetton saw it
She shared another screenshot of a message from Don Jr. from 2011 that was a reply to a tweet of
hers in which she wrote that she planned to douse her body in bacon, one of his favorite scents
Along with a winking smiley face, he reportedly wrote, Stop that. I'm a happily married man
Vanessa Trump filed for divorce in March 2018 right before Danity Kane singer and reality TV personality Aubrey O claimed to have had a year affair with Don Jr after meeting him on the set of The Apprentice in 2011 According to US Weekly the affair ended when Vanessa discovered emails between the two of them
They ultimately decided to stay together at the time. In the aftermath of the divorce
O'Day began revealing details of the affair. During a 2023 interview on the Sophia with an F
podcast, she claimed that at one point, Don Jr. was ready to leave Vanessa for her
It was, I'm leaving my wife and kids and this is going to be what I want and I love you and
you're my wife and everybody knows what it is. OJ also claimed that Trump lawyer Michael Cohen
helped bury news of the affair for years. Don Jr. has never publicly commented on the alleged affair
In October 2017, Donald Trump Jr. made his views about a certain political philosophy known on
social media through somewhat questionable means. On Halloween, he shared a photo of his young
daughter, Chloe, in a police outfit, holding a bucket of candy, along with the caption
I'm going to take half of Chloe's candy tonight and give it to some kid who sat at home
It's never too early to teach her about socialism. The photo and the remark got plenty of attention
including from Harry Potter author J.K. Rowling, who chimed in, Fill her bucket with old candy left by her great-grandfather
then explained that she has more because she's smarter than all the other kids. Overall, this comment was met with a mixed reception, though Don Jr. apparently remained
unfazed, especially considering his reputation for making outlandish remarks. Either way, we hope that Khloe was able to sidestep her dad's political point-making and reap the rewards of
her Halloween bounty. Give me that candy! John Jr. made a bold move in 2017 when he decided to relinquish his Secret Service protection
As reported by the Florida Times-Union, a close friend of his revealed that he wanted to give up
the 24-hour security detail for himself, as well his wife and five children. Secret Service
representative, Catherine Mahouan, declined to comment on the terms of the family's protection
agreement. Insiders claimed that Don Jr. made the decision in order to lead a more private life
but it nevertheless posed serious risks. As Jonathan Wackrow, a former member of Barack
Obama's security team, noted, in today's global risk environment, waiving this detail poses great
danger to him and to his family. What he is becoming, potentially, is a target of opportunity
People who want to lash out at the president are going to seek that path of least resistance
This decision is negligent. As the free engagement ring story makes clear Donald Trump Jr isn exactly known for being a big spender In fact he has a reputation for nickel and diming his way through life According to Page Six one of the reasons that Vanessa filed for divorce was her ex
cheap lifestyle. As an insider revealed, 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
Sources also claim that Don Jr. treated Vanessa like a, quote, second-class citizen and that she had to borrow money from her mother. However
her spokesperson debunked those allegations, insisting to Page Six, all of these claims are simply not true. Don and Vanessa have tremendous respect for each other
and always have. The notion that she has had to rely on her family for assistance is absolutely
false and utterly ridiculous. Insiders close to the couple told a different story, though
claiming that they lived separate lives for years. As one source told People magazine in 2018
even before all this Trump presidency stuff started, they weren't good. And their marriage
restrained. There's been speculation that Vanessa inherited a large fortune after her father's
passing and that this made it easier for her to finally divorce Don Jr. According to Page Six
Vanessa's father, Charles Hayden, had invested in several stocks and assets that eventually
matured following his death in 2005. As a source claimed, I can't speculate as to how much they
received, but it was life-changing. The amount was reportedly enough for Vanessa's mother
Bonnie Hayden, to pay $6.5 million in cash for a lavish penthouse in New York City. And it may
have also been the straw that broke the camel's back of Vanessa's strained marriage. But money was
far from the only issue, as Don Jr.'s alleged infidelity was also a problem throughout their
relationship. As the source noted, there have been numerous affairs. This divorce has been in
the works for a long time. Vanessa Trump made headlines in 2021 when it was reported that she
was in a romantic relationship with a Secret Service agent during her former father-in-law's
presidency. According to Washington Post reporter Carol Lenig's book, Zero Fail, The Rise and Fall
of the Secret Service, Vanessa and her former sister-in-law, Tiffany Trump, reportedly became
close to the agents who protected them, to an inappropriate degree. Lenig didn't specify if Vanessa began dating the agent before or after she filed for divorce
although that didn't stop tabloid speculation that she may have been having an affair. Vanessa's representatives didn't comment on the controversy, although Tiffany's reps released
a statement to The Washington Post that read, Tiffany's experience with the Secret Service was entirely professional