Breaking News: Who is Vanessa Trump? A Look at the Former Model, Mother, and Ex-Wife of Donald Trump Jr. Now Dating Tiger Woods….See More

On March 23, 2025, golf legend Tiger Woods took to social media to confirm a romance that had been swirling in gossip circles for weeks:

he is dating Vanessa Trump, the former daughter-in-law of U.S. President Donald Trump.

With a heartfelt caption—“Love is in the air and life is better with you by my side!”—accompanied by two cozy photos, Woods made the relationship Instagram-official, thrusting Vanessa Trump back into the spotlight.

But who is this woman who has captured the heart of one of the world’s most famous athletes? From her early days as a model to her high-profile marriage and beyond, here’s a comprehensive look at Vanessa Trump’s life and her new chapter with Tiger Woods.

Early Life and Rise to Fame
Vanessa Trump was born Vanessa Kay Pergolizzi on December 18, 1977, in New York City.

Raised on Manhattan’s Upper East Side, she grew up in a world of privilege and ambition.

Her mother, Bonnie Kay Haydon, ran Kay Models, a prominent modeling agency, while her stepfather, Charles Haydon, was a successful lawyer.

This environment naturally paved the way for Vanessa’s entry into the modeling world.

As a teenager, she signed with Wilhelmina Models, one of the top agencies of the 1990s, and quickly made a name for herself in the industry.

Vanessa’s early career wasn’t limited to posing for photos. She showed an entrepreneurial streak, co-founding a nightclub called Sessa with her sister Veronika in 2003.

She also ventured into acting, landing a small role in the 2003 romantic comedy Something’s Gotta Give, starring Jack Nicholson and Diane Keaton. However, it was her personal life that would soon catapult her into broader public awareness.

Before her modeling days took off, Vanessa’s teenage years included a rumored romance with local street gangster Valentin Rivera, hinting at a rebellious streak.

Later, she was linked to high-profile figures like actor Leonardo DiCaprio and Saudi Prince Khalid bin Bandar bin Sultan Al Saud, showcasing her appeal across diverse circles.

These early relationships foreshadowed the headline-making life she would lead.

Marriage to Donald Trump Jr.
Vanessa’s life changed dramatically in 2003 when she met Donald Trump Jr., the eldest son of real estate mogul and future U.S. President Donald Trump.

The introduction came courtesy of Donald Trump himself at a fashion event. Two years later, on November 12, 2005, Vanessa and Don Jr.

tied the knot in a lavish ceremony at the Trump family’s Mar-a-Lago estate in Palm Beach, Florida.

The wedding marked the beginning of a 12-year union that would place Vanessa at the heart of one of America’s most scrutinized families.

Together, Vanessa and Don Jr. had five children: Kai Madison (born 2007), Donald John III (born 2009), Tristan Milos (born 2011), Spencer Frederick (born 2012), and Chloe Sophia (born 2014).

Vanessa embraced motherhood with dedication, often praised by family members for her parenting skills. Ivanka Trump, her former sister-in-law, once called her “Wonder Woman” for her ability to juggle raising five kids while maintaining an active life.

Despite the glamorous facade, the marriage faced challenges. In March 2018, Vanessa filed for an uncontested divorce, signaling an amicable split.

The divorce was finalized by the end of that year after resolving custody arrangements. Post-divorce, Vanessa and Don Jr.

maintained a cordial relationship, occasionally appearing together at family events and Mar-a-Lago gatherings.

Don Jr. soon began dating former Fox News host Kimberly Guilfoyle, while Vanessa kept a lower profile—until now.

Life After Divorce
Following her split from Don Jr., Vanessa retreated from the intense public scrutiny that came with being a Trump.

She settled in Palm Beach, Florida, just 20 minutes from Tiger Woods’ residence, focusing on raising her children.

Her eldest daughter, Kai, emerged as a standout junior golfer, attending The Benjamin School alongside Woods’ children, Sam and Charlie.

Kai’s passion for golf—she’s set to play for the University of Miami in 2026—likely provided a natural connection point between Vanessa and Woods.

Vanessa also inherited a significant fortune after her mother’s death in 2018, tied to a condiment business started by her late stepfather, adding to her financial independence.

While she stepped back from modeling and acting, her past ventures—like a handbag line launched during her marriage—reflected her creative and business-minded spirit.

The Tiger Woods Connection
Rumors of Vanessa Trump and Tiger Woods dating began circulating in early 2025, fueled by sightings at golf events.

Vanessa and Kai were spotted at Woods’ Genesis Invitational in February, where he handed out the trophy, and at TGL matches in Palm Beach Gardens.

Reports suggest their relationship began around Thanksgiving 2024, blossoming quietly before Woods’ public announcement.

Woods, a 15-time major golf champion, has a storied personal life of his own. After his 2010 divorce from Elin Nordegren—following a highly publicized infidelity scandal—he dated Olympic skier Lindsey Vonn and later Erica Herman, a relationship that ended messily in 2022.

Now 49, Woods appears to have found stability with Vanessa, 47. Sources say their bond is rooted in shared values as parents and their proximity in South Florida’s elite circles.

The couple’s children attending the same school likely deepened their connection.

Kai and Charlie Woods even competed together in a junior golf tournament in March 2025, just days before Woods’ announcement.

Meanwhile, Woods’ friendship with Donald Trump—who awarded him the Presidential Medal of Freedom in 2019—adds another layer to this intertwining narrative.

Insiders report that Don Jr. is “cool” with the relationship, and Ivanka Trump commented “So happy for you both” on Woods’ post, signaling family approval.

A New Chapter
Tiger Woods’ Instagram post on March 23, 2025, marked a rare personal revelation from the notoriously private golfer.

Alongside photos—one of the couple posing, another of them lounging in a hammock—Woods wrote, “We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts.”

The announcement came amid Woods’ recovery from a ruptured Achilles tendon, sidelining him from the Masters, but his spirits seem high with Vanessa by his side.

Vanessa Trump’s journey—from a Manhattan model to a Trump family member, and now to Tiger Woods’ partner—reflects a life of reinvention.

With a rich dating history, a successful stint in the public eye, and a focus on family, she brings a unique blend of resilience and grace to this high-profile romance.

As the world watches this unexpected pairing, Vanessa remains a figure of intrigue, stepping into yet another chapter that promises to keep us captivated.