In June 2006, Jennifer Aniston sat in the crowd at Roland Garros and watched Roger Federer lose the French Open final. That’s the entire relationship between them, one afternoon at a tennis match, nothing more. What makes the day worth knowing about is what happened to Federer on the court that afternoon, in a match that ended up shaping the next three years of his career.
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What was at stake for Federer that day
Federer arrived at Roland Garros as the top-ranked player in the world, a ranking he held for the entire 2006 season. He had lost only three matches all year, and all three were to the same opponent, Rafael Nadal, in the finals at Dubai, Monte Carlo, and Rome. Going into Paris, Federer had never lost a Grand Slam final. He had won his first seven. A win here would have completed his career Grand Slam and made him the first man since Rod Laver in 1969 to hold all four major titles at once, a feat nobody repeated until Novak Djokovic managed it at the same tournament a decade later.
Federer took the first set 6-1, playing the tennis that had carried him through those seven finals. Then, serving at 40-0 in the second set, he missed a routine volley into the net. He lost that game, and with it, the match. Nadal had turned 20 just eight days earlier. He took the next three sets, 6-1, 6-4, and 7-6(4), for his second French Open title. It was the first Grand Slam final the two of them had ever played against each other.
Federer still finished the season 92-5, a record Tennis.com later ranked as the second-best of the Open era, behind only Rod Laver’s 1969. His only Grand Slam loss all year happened in that one match.
It also wasn’t a one-time result. Nadal beat Federer in the French Open final again in 2007, then again in 2008, this time in straight sets.
| Year | Roland Garros men’s final |
|---|---|
| 2006 | Nadal def. Federer, 1-6, 6-1, 6-4, 7-6(4) |
| 2007 | Nadal def. Federer |
| 2008 | Nadal def. Federer, in straight sets |
Federer finally won the French Open in 2009, the year Nadal was upset in the fourth round by Robin Sรถderling, which completed Federer’s career Grand Slam. Their rivalry ran until 2019, when they played their last professional match, a Wimbledon semifinal. Nadal finished it 24-16 in his favor.
Why Aniston was even in Paris
Aniston and Vince Vaughn had been dating since 2005, when they met filming “The Break-Up” together, the same year Aniston filed for divorce from Brad Pitt. The film opened in American theaters on June 2, 2006, nine days before the French Open final, and the two of them spent that week promoting it across Europe. The day after Federer lost to Nadal, Aniston, Vaughn, and director Peyton Reed showed up at a screening of the film in Hamburg. Wire photos from the French Open, credited to the Associated Press and widely archived by Getty Images, are the only record of Aniston and Federer ever being in the same place. There’s no record of them meeting, and nothing connecting them beyond that afternoon in the stands.
Aniston’s dating life has been covered for two decades: a marriage to Justin Theroux, a long relationship with Vaughn, and rumors along the way involving her “Friends” co-star David Schwimmer and, at least once, Barack Obama. Federer has never been part of any of it.
The relationship with Vaughn ended a few months after Paris. Representatives for both confirmed the split to People in early December 2006, describing it as mutual.
Both of them now
Aniston has been with wellness author and hypnotherapist Jim Curtis since 2025. The two of them were first photographed together in Mallorca that July, and Aniston made the relationship Instagram official in November. By May 2026, a source told People the couple had already marked a full year together, which suggests the relationship started sometime before the Mallorca trip became public.
Federer retired from professional tennis in September 2022. He married his wife, Mirka, in 2009, after they met representing Switzerland at the 2000 Sydney Olympics. He has been back at Wimbledon every year since retiring, and this July he was in the Royal Box again, watching from the stands instead of playing.
