The Glaringly Obvious Sign Don Jr. & Vanessa Trump's Relationship Was Doomed From The Beginning

Vanessa Trump and Donald Trump Jr.'s relationship started on a decidedly weird note. During a 2006 interview with the New York Times, the socialite recalled how she was at a fashion show in 2003 when Donald Trump approached her and introduced his eldest son. After a short and awkward chat, everyone went back to their seats. However, later in the night, the real estate magnate seemingly forgot that he had already spoken to Vanessa and approached her a second time to introduce Don Jr. Thankfully, the now-president wasn't around when the pair ran into each other a third time at a party just a few weeks later, and they wound up having a relatively normal conversation.

Although Vanessa used an offensive slur to describe Donald's memory flub from their first meeting, Don Jr. wasn't fazed. The happy couple tied the knot in 2005 and subsequently welcomed five children. However, they ultimately parted ways in 2018. In the aftermath of their split, Christine Scott, Vanessa's publicist, informed the New York Times that another glaring issue plagued the early days of their relationship. 

"I know she wasn't thrilled that he hunted as he did," Scott revealed. "I know she wanted to keep it on the DL. She knew that was going to be a big issue, socially." It's never a good sign when your partner dislikes such a major part of your life. However, in Don Jr. and Vanessa's case, it may have been a bigger problem because of just how much he loves hunting, even though it has notably got him into trouble over the years.

It seems like pretty much every time Donald Trump Jr. has some free time, he grabs his gun and heads straight into the woods to hunt. More often than not, the businessman also chronicles his hunting trips in Instagram posts and Stories. Unfortunately, in doing so, Don Jr. has shared several awkward photos with his now ex-fiancée Kimberly Guilfoyle that should have probably stayed in the camera roll. Still, it's safe to say that the president's eldest son doesn't treat hunting as a casual pastime but a deeply-rooted passion. 

In fact, in 2019, a New York Post insider shared a weird detail about Guilfoyle and Don Jr.'s relationship that everyone ignored at the time. According to the source, the political activist had an important concern while they were house hunting in the Hamptons, which they divulged to the outlet: "One of the first questions Don Jr. asked was where he could store his guns." Don Jr. wasn't fazed after learning that the luxurious property didn't come with a designated gun room since they could create a new room for gun storage purposes. 

The insider also confirmed that Don Jr. was eagerly awaiting the hunting season in the area because it was filled with like-minded hunters and gun owners. In fact, there was even a time when one of Don Jr.'s hunting trips could have landed him in court, but even that wasn't enough to keep him away from the sport. Given all this, it's unsurprising that Vanessa Trump's dislike for hunting didn't sit too well with her now ex-husband.