Who is Donald Trump Jr.’s Girlfriend? A Comprehensive List

As the eldest son of former President Donald Trump, Donald Trump Jr. has always been under the public eye. Along with his business ventures and political involvement, his personal life has also attracted significant attention. In this blog post, we will provide you with a detailed list of Donald Trump Jr.’s girlfriends throughout the years.

1. Vanessa Trump (née Haydon)

Donald Trump Jr.’s most well-known and high-profile relationship to date is his marriage to Vanessa Trump. The couple tied the knot in November 2005 after a two-year courtship. They have five children together – Kai Madison, Donald III, Tristan Milos, Chloe Sophia, and Spencer Frederick.

Vanessa Trump, born Vanessa Kay Haydon on December 18, 1977, in New York City, is a former model and actress. She appeared in films such as “Something’s Gotta Give” and “High School Musical 3: Senior Year.”

Their marriage lasted for more than a decade, but the couple announced their separation in March 2018 and finalized their divorce in February 2019.

2. Kimberly Guilfoyle

Following his divorce from Vanessa Trump, Donald Trump Jr. started dating Kimberly Guilfoyle, a prominent political analyst and television personality. Guilfoyle was formerly married to Gavin Newsom, the governor of California.

Kimberly Guilfoyle, born on March 9, 1969, in San Francisco, California, gained recognition as one of the co-hosts of the Fox News program “The Five.” She later joined the Trump campaign as a senior advisor for President Trump’s re-election bid in 2020.

Donald Trump Jr. and Kimberly Guilfoyle have been dating since mid-2018 and have been actively involved in political campaigns and public appearances together.

3. Aubrey O’Day

Prior to his relationship with Kimberly Guilfoyle, Donald Trump Jr. was romantically linked to Aubrey O’Day, an American singer-songwriter and former member of the girl group Danity Kane.

Their relationship reportedly started in late 2011 after meeting on the set of the reality show “Celebrity Apprentice,” where Donald Trump Jr. served as an advisor alongside his father. However, their affair ended in 2012.

Aubrey O’Day, born on February 11, 1984, in San Francisco, California, gained prominence through her musical career and appearances on reality TV shows like “Making the Band.”

4. Hiking and Fishing Adventures

In addition to his known relationships, Donald Trump Jr. has also been spotted enjoying outdoor activities, particularly hiking and fishing, with various companions over the years. These hiking and fishing partners have included friends, family members, and colleagues, but none have been confirmed as romantic partners.

It is important to note that personal relationships are subject to change, and the information presented in this blog post reflects the relationships that were publicly reported at the time of writing. Any updates or additions to Donald Trump Jr.’s girlfriend list may not be covered in this article.


Donald Trump Jr.’s personal life has undoubtedly been the subject of considerable interest among the media and the public. While his marriage to Vanessa Trump and ongoing relationship with Kimberly Guilfoyle are well-known, his previous relationship with Aubrey O’Day offers a glimpse into his romantic past.

It’s essential to remember that public figures deserve their privacy, and it’s crucial to respect their personal lives. As individuals, they have the right to maintain confidential relationships without constant scrutiny. This article serves as an overview of past and current relationships in order to provide the information readers may be seeking.

Disclaimer: The information provided in this article is based on publicly available sources and is accurate to the best of our knowledge at the time of writing.

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