Donald Trump Jr.’s Relationship History: Exploring the Names of His Girlfriends

As the son of the 45th President of the United States, Donald Trump Jr. has drawn attention from the media and the public alike. From his business ventures to his political involvement, every facet of his life has been under scrutiny. One aspect that often sparks curiosity is his romantic relationships. In this blog post, we will delve into the names of Donald Trump Jr.’s past girlfriends and explore the history of his love life.

Vanessa Trump: A High School Sweetheart Turned Wife

Perhaps the most well-known of Donald Trump Jr.’s romantic partners is Vanessa Trump, his former wife. The couple first met in 2003 while attending a fashion show. They quickly hit it off and began dating. After a whirlwind courtship, they got engaged and tied the knot in November 2005.

Vanessa Trump, born Vanessa Kay Haydon, is a model and actress. Throughout their relationship, she supported Donald Trump Jr. in his business ventures and actively participated in the Trump family’s public appearances. The couple shared five children: Kai, Donald III, Tristan, Spencer, and Chloe.

However, their marriage encountered significant strain, and in 2018, the couple announced their separation. While they attempted to reconcile, their relationship ultimately ended in divorce in February 2019.

Aubrey O’Day: A Controversial Affair

During the time of Donald Trump Jr.’s separation from his wife, rumors emerged of an alleged affair with singer Aubrey O’Day. O’Day, a former member of the girl group Danity Kane, reportedly had a relationship with Trump Jr. from 2011 to 2012.

This rumored affair attracted significant media attention, further fueled by leaked text messages between O’Day and Trump Jr. that circulated online. Both parties have remained relatively tight-lipped about the alleged affair, leaving much of it open to speculation.

Kimberly Guilfoyle: A Shared Passion for Politics

Following his divorce from Vanessa Trump, Donald Trump Jr. found love in an unexpected place: the political arena. He began dating Kimberly Guilfoyle, a former Fox News host and a prominent campaign surrogate for President Trump.

Guilfoyle, known for her strong conservative views, brings significant political expertise to the relationship. She was previously married to Gavin Newsom, the current Governor of California, and has built a successful career in media and politics.

The couple made their relationship public in 2018 and have been together ever since. They actively support Republican candidates and frequently attend political events together, showcasing their shared passion for conservative causes. Guilfoyle has also taken on a role within the Trump organization, serving as a senior advisor to Donald Trump Jr.

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Vanessa Trump Aubrey O’Day Kimberly Guilfoyle

Amidst Speculation: Unconfirmed Relationships and Rumors

While the three aforementioned women have been publicly linked to Donald Trump Jr., there have been other rumors and unconfirmed relationships surrounding his personal life.

One such rumor involved former model and television personality Melissa Diggs. While the exact nature of their relationship remains unclear, some speculations suggest that they were romantically involved.

Similarly, there have been rumors of Trump Jr. dating Fox News host and journalist Kimberly Halkett, but neither party has confirmed these speculations.

It is essential to remember that rumors and unconfirmed relationships should be taken with a grain of salt. Privacy and personal lives often become the subject of gossip and tabloid speculation, and separating fact from fiction can be challenging.


Donald Trump Jr.’s romantic history has been closely followed by the media and public due to his prominent family background. From his high school sweetheart turned wife, Vanessa Trump, to the rumored affair with Aubrey O’Day and his current partner Kimberly Guilfoyle, his personal relationships have garnered significant attention.

As with any public figure, privacy remains an essential aspect of their personal lives, and it is crucial to respect boundaries. While speculation and rumors may persist, it is important to remember that everyone deserves to maintain a certain level of privacy and dignity.

As new chapters unfold in Donald Trump Jr.’s life, it will be interesting to see how his romantic relationships evolve and whether any new names will be added to this list.


  1. People: Donald Trump Jr. Apologizes for Sharing Aubrey O’Day’s Tweet About Him and Vanessa When She Was Pregnant
  2. Business Insider: A look at Donald Trump Jr.’s romantic history, including his messy divorce
  3. Page Six: Vanessa Trump news, articles, and gossip
  4. Fox News: Kimberly Guilfoyle

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