Donald Trump Jr. And Ex-Wife Vanessa's Complete Relationship Timeline

Donald Trump Jr. and Vanessa Trump have come a long way since they were introduced at a party in 2003. According to an interview Vanessa gave The New York Times, Donald Trump Sr. took it upon himself to introduce them: "Hi, I'm Donald Trump. I wanted to introduce you to my son Donald Trump Jr." But far from being the perfect wingman, Donald Sr. apparently forgot that he ever introduced them and tried to introduce them for the second time later that night.

However, the couple was meant to be because they ran into each other at another party weeks later. And without Daddy Donald there to kill the vibe, the two quickly hit it off. Vanessa explained that she and Don Jr. didn't remember each other despite their dramatic introduction until mid-way into their conversation. "Wait, you were at that fashion show. Wait, you're 'the one with the re***ded dad!'" Despite this, they started dating and soon fell in love — at least, we assume they did since Don Jr. proposed a year later in 2004.

One year after their engagement, Donald Trump Jr. and Vanessa Trump married at Mar-a-Lago. They welcomed their first daughter, Kai Trump, in 2007 and their first son two years later, in 2009. In 2011, Vanessa was pregnant with their third child, Tristan Trump. It was during this pregnancy that Donald Jr. reportedly pursued an affair with Aubrey O'Day. Vanessa Trump found out that Don Jr. was cheating through his phone, but the couple worked through the hitch and even had two more babies. They had Spencer Trump the following year and their last child, Chloe Trump, two years later in 2014.

Beneath the surface, sources claim that their marriage was already in trouble by this time. Despite his wealth, Page Six reported that Don Jr. was stingy with money and was rarely home. Their marital issues continued into 2015 when Donald Trump Sr. started his presidential campaign. This likely worsened tensions, considering the time Don Jr. spent supporting his father on the road and Vanessa's family's liberal views.

One year after Donald Trump started his the presidency, Donald Trump Jr.'s family received a terrifying package containing an unknown white powder. Vanessa Trump, who had opened it, was quickly rushed to the hospital to determine if she or her children were in any danger. The following month, in March 2018, she filed for an uncontested divorce. The "uncontested tag" indicated that Don Jr. was in agreement.

In May 2018, Page Six reported that Vanessa had inherited millions shortly before filing for divorce. They also speculated that this was why she finally had the courage to leave her soon-to-be ex. By July, their divorce became a contested issue that dragged out until the end of 2018. The ex-couple officially announced that their divorce was final in February 2019. Donald Trump Jr. quickly began a relationship with Kimberly Guilfoyle, and Vanessa was rumored to have a relationship with a secret service agent who had worked with her family.