Don Jr., meanwhile, had at that point been working at the Trump Organization for a few years.
The pair married in 2005 at the Mar-a-Lago Resort in West Palm Springs.
"Donald Trump Sr. had taken his son to task on "Larry King Live" for accepting a free engagement ring from a jeweler at a mall in New Jersey in exchange for publicly announcing his engagement there," The New York Times reported. "'You have a name that is hot as a pistol, you have to be very careful with things like this,' the elder Trump told King."
Vanessa was a common presence on the charity circuit. While Don Jr. spent his early 20s hiding from the spotlight, the pair began to make headlines together more frequently after they married.
Don Jr. aggressively advocated for his father and attacked critics on social media.
Trump has been under investigation for his role in potential Russian meddling in the election, after The New York Times reported in July 2017 that he met with a Russian lawyer who had told him she had damaging information about Hillary Clinton.
Sources told The New York Post that Donald Jr.'s obsession with politics and frequent travels were contributing to issues in the relationship.
One source said: "Vanessa is by nature is a very low-key person, and she is uncomfortable with the attention her family is getting now the Trumps are on the world stage. She is also worried for her kids, particularly after she received the threatening letter containing the white powder."