Before Andre Agassi became one of tennis’s most celebrated legends and settled into his decades-long marriage with Steffi Graf, his early romantic life frequently captured international headlines. During his initial rise on the ATP Tour in the late 1980s, Agassi’s primary early girlfriend was Wendi Stewart, a native of Las Vegas who stood by him as he transformed from a rebellious teenage prodigy into a Grand Slam champion.
As Agassi’s celebrity status exploded beyond the tennis court, his relationship history evolved from his hometown romance with Stewart to high-profile pairings with cultural icons like Barbra Streisand and actress Brooke Shields. Understanding Agassi's early romantic timeline offers a fascinating window into his complex personal journey, his struggle with early fame, and the emotional evolution detailed in his critically acclaimed 2009 autobiography, Open.
Wendi Stewart: The Early Las Vegas Sweetheart
Long before the flashbulbs of Hollywood caught up with Andre Agassi, his most significant early relationship was with Wendi Stewart. Met during his formative years in Las Vegas, Nevada, Stewart was a comforting, grounding presence for Agassi as he navigated the intense pressure of professional tennis in the late 1980s and early 1990s.
Meeting and Early Relationship Dynamics
Agassi grew up under the intense, uncompromising tutelage of his father, Mike Agassi, before being sent to the Nick Bollettieri Tennis Academy in Bradenton, Florida. Amid the grueling demands of his early training and sudden entry into the pro ranks in 1986 at age 16, meeting Wendi Stewart provided Agassi with a rare connection to home and normalcy outside the hyper-competitive world of elite sports.
Stewart was widely recognized by tennis broadcasters and fans during the late 1980s, frequently appearing in Agassi’s player box during major tournaments. During Agassi’s early appearances at French Open finals and his run to the 1992 Wimbledon title, Stewart was a constant fixture, offering emotional support as Agassi wrestled with high expectations, intense media scrutiny, and inner doubts about his career path.
The Impact of Early Fame on Their Romance
As Agassi’s public image took off—amplified by his flamboyant neon apparel, long hair, and famous Nike "Image is Everything" campaign—the demands on his personal life grew exponentially. Maintaining a low-key relationship under the relentless glare of international media proved increasingly difficult.
In Open, Agassi reflected candidly on his early years, describing how his personal relationships often served as an anchor while he fought against feeling alienated by his own celebrity. Despite their close bond and shared roots in Las Vegas, the pressure of Agassi’s grueling tour schedule and rapidly expanding superstar world eventually led the couple to separate in the early 1990s.
The Barbra Streisand Era: A High-Profile Media Sensation
Following his relationship with Wendi Stewart and his breakthrough Grand Slam victory at Wimbledon in 1992, Agassi embarked on one of the most unexpected and heavily publicized relationships of the 1990s: his romance with legendary singer and actress Barbra Streisand.
[ late 1980s ] [ 1992 - 1993 ] [ 1993 - 1999 ] [ 2001 - Present ] Wendi Stewart -------> Barbra Streisand -------> Brooke Shields -------> Steffi Graf (Hometown Sweetheart) (Cultural Icon Era) (First Marriage) (Marriage & Legacy)
How the Relationship Began
The connection between Agassi and Streisand began after Streisand watched Agassi play and reached out to express her admiration for his talent and intensity. Despite an age difference of 28 years—Agassi was in his early twenties while Streisand was in her fifties—the two developed a deep emotional friendship that quickly blossomed into a romantic courtship between 1992 and 1993.
Streisand became a frequent guest in Agassi’s box at major tournaments, including the US Open. Her presence ignited an unprecedented media frenzy, with tabloid outlets and sports commentators alike fascinated by the pairing of a young tennis rebel and an established entertainment icon.
Public Reaction and Agassi's Reflection
The public reaction to Agassi and Streisand was characterized by intense fascination and frequent judgment from traditional media outlets. However, Agassi consistently spoke of Streisand with immense respect and affection. In his autobiography, Agassi explained that the age gap never bothered him, noting that Streisand’s intellect, sensitivity, and shared understanding of intense public scrutiny made her a vital ally during a tumultuous period in his life.
Agassi famously described their bond by stating that dating Streisand was like "wearing hot lava," acknowledging both the passion and the overwhelming public burn that accompanied such a high-profile union. Though their romantic relationship was relatively brief, they remained lifelong friends based on mutual admiration.
Marriage to Brooke Shields: Celebrity Culture Meets World No. 1
In late 1993, Agassi began dating supermodel and actress Brooke Shields. Their relationship quickly grew into one of the defining celebrity courtships of the mid-to-late 1990s, culminating in a lavish wedding in 1997.
Courtship and Shared Struggles
Agassi and Shields were introduced via fax machine by a mutual acquaintance while Agassi was competing abroad. Both had grown up in the spotlight under the intense management of ambitious parents—Shields as a child star and famous model, Agassi as a tennis prodigy. This shared background created an immediate empathetic bond.
Throughout the mid-1990s, Shields was instrumental in encouraging Agassi, particularly during his rise to the ATP World No. 1 ranking in 1995. However, this period was also marked by deep physical and emotional volatility for Agassi, who suffered from severe back injuries, lost motivation, and saw his ranking plunge to No. 141 in 1997.
Challenges and Divorcing in 1999
The couple married on April 19, 1997, in Monterey, California. However, the marriage faced immediate obstacles due to contrasting career commitments, personal struggles, and Agassi’s unaddressed personal conflicts regarding his passion for tennis.
During this era, Agassi notoriously experimented with crystal meth—a dark period he later disclosed in Open—and struggled with his self-identity. Recognizing that they had grown apart and wanted different things out of life, Agassi and Shields officially filed for divorce in 1999 after less than two years of marriage. The dissolution was handled amicably, paving the way for both to find long-term stability with future partners.
Chronological Overview of Andre Agassi's Major Relationships
To better understand the timeline of Andre Agassi's romantic history from his early career through his high-profile relationships, the table below highlights key partners, timeframes, and public milestones.
| Partner | Relationship Period | Nature of Relationship | Key Milestones & Context |
|---|---|---|---|
| Wendi Stewart | Late 1980s – Early 1990s | Early Long-Term Girlfriend | Hometown relationship from Las Vegas; supported Agassi during his early ATP Tour rise and 1992 Wimbledon win. |
| Barbra Streisand | 1992 – 1993 | High-Profile Romance | Major media attention; provided emotional support during Agassi's initial transition to Grand Slam champion status. |
| Brooke Shields | 1993 – 1999 | Dated (1993–1997), Married (1997–1999) | High-profile celebrity marriage; coincided with Agassi reaching World No. 1, his 1997 slump, and his subsequent career rebuild. |
| Steffi Graf | 1999 – Present | Married (October 2001 – Present) | Union of tennis legends; married in Las Vegas; two children (Jaden Gil and Jaz Elle); active in philanthropic efforts. |
Steffi Graf: Finding Ultimate Stability and Shared Purpose
Following his divorce from Brooke Shields in 1999, Agassi’s life underwent a profound transformation, both professionally and personally. At the 1999 French Open, Agassi won his historic title to complete his career Grand Slam. That same weekend, German tennis icon Steffi Graf won the women's singles title.
A Shared Life Built on Understanding
Agassi had long harbored a silent admiration for Graf, having tried unsuccessfully to talk to her at official champions' dinners earlier in his career. In late 1999, after both had ended previous long-term relationships, they began dating discreetly.
Unlike his past relationships, which were often played out in front of paparazzi and Hollywood cameras, Agassi’s relationship with Graf was rooted in shared quietness, professional discipline, and mutual respect for privacy. Graf understood the extraordinary physical and mental demands of elite tennis, having won 22 Grand Slam singles titles herself.
Marriage and Family Life in Las Vegas
Agassi and Graf married on October 22, 2001, in an intimate ceremony at their home in Las Vegas, with only their mothers in attendance. Shortly after, they welcomed their first child, son Jaden Gil, followed by daughter Jaz Elle in 2003.
Over the past two decades, the couple has remained one of sports' most enduring power couples. Together, they have focused heavily on education and philanthropy, primarily through the Andre Agassi Foundation for Education and the launch of charter schools serving underprivileged youth in Las Vegas.
How Agassi's Early Love Life Shaped His Career and Identity
Agassi's romantic journey directly mirrored his search for self-identity throughout his professional tennis career. For much of his youth, Agassi struggled with feeling that his identity was forced upon him—first by a demanding father, then by sponsors, and finally by a public eager to label him a rebel.
Early Career Rebel Mid-Career Slump Career Rebirth & Legacy - Wendi Stewart (Grounding) - Brooke Shields (Marriage) - Steffi Graf (Partnership) - Early ATP titles - World No. 1 to No. 141 ranking - Career Grand Slam completed - First Grand Slam (1992) - Rebuilding on Challenger tour - Foundation & Philanthropy focus
- The Search for Grounding: Wendi Stewart provided a vital link to normalcy and home during the tumultuous years when Agassi felt overwhelmed by the commercialization of his image.
- The Magnetism of Celebrity: His time with Barbra Streisand and Brooke Shields reflected his entry into mainstream pop culture, exposing the challenges of balancing high-stakes entertainment lifestyle with the solitary demands of world-class athletics.
- Maturity and Fulfillment: His eventual union with Steffi Graf marked a complete evolution into personal maturity, helping Agassi reconcile his relationship with tennis and focus on meaningful post-retirement work.
In Open, Agassi noted that surviving the turbulence of his early twenties allowed him to appreciate true connection when he finally found it, turning what could have been a cautionary tale of early stardom into one of sports' most successful second acts.
Frequently Asked Questions
Who was Andre Agassi’s first serious girlfriend during his early tennis career?
Andre Agassi’s primary early girlfriend during his initial rise on the ATP Tour in the late 1980s was Wendi Stewart. She was a childhood sweetheart from his hometown of Las Vegas, Nevada, and frequently accompanied him to early tournaments, including his 1992 Wimbledon victory.
Did Andre Agassi really date Barbra Streisand?
Yes. Agassi dated singer and actress Barbra Streisand between 1992 and 1993. Despite an age gap of 28 years, the two formed a close bond after Streisand watched him play tennis. Agassi spoke warmly of their relationship in his autobiography Open, describing her as an insightful and empathetic partner during a high-pressure era of his life.
How long were Andre Agassi and Brooke Shields married?
Andre Agassi and Brooke Shields began dating in late 1993 and were married on April 19, 1997. Their marriage lasted just under two years; they officially divorced in 1999, citing growing personal differences and demanding, separate careers.
When did Andre Agassi marry Steffi Graf?
Andre Agassi married tennis legend Steffi Graf on October 22, 2001, in a private ceremony in Las Vegas. The couple began dating in 1999 after both won the singles titles at the French Open that year.
Did Andre Agassi write about his early girlfriends in his book Open?
Yes. In his 2009 autobiography Open, Agassi candidly discussed his early relationships, detailing how Wendi Stewart, Barbra Streisand, and Brooke Shields impacted his personal development, his mental state on the court, and his eventual journey toward personal stability with Steffi Graf.
Summary and Key Takeaway
Andre Agassi’s early romantic life was as dynamic as his historic tennis career. From his hometown sweetheart Wendi Stewart—who provided stability during his early rise—to high-profile courtships with Barbra Streisand and Brooke Shields, Agassi’s relationships reflected his ongoing search for personal identity under extreme public spotlight. Ultimately, his union with Steffi Graf provided the quiet support and shared foundation that defined the second half of his career and his post-tennis life.
For readers interested in a deeper look at Agassi's personal evolution, reading his autobiography Open offers an unmatched, firsthand perspective on how these early relationships shaped one of the greatest champions in modern sports history.
