Hollywood's Sunset Tower Hotel was the scene of a near-miss this week, as former flames Jennifer Aniston and John Mayer were spotted leaving the iconic venue within just 40 minutes of each other. The coincidence has sent fans and tabloids into a nostalgic frenzy, recalling the pair's headline-grabbing, on-off romance that began over a decade ago.
A Hollywood Hotspot Hosts an Unplanned Encounter
On Thursday evening, Friends icon Jennifer Aniston, 56, was seen departing the famed Sunset Tower Hotel in West Hollywood with a group of close female friends. Among her entourage was Molly McNearney, the wife of talk show host Jimmy Kimmel. The actress, cutting a characteristically chic figure in black, was photographed holding her hair against the breeze before slipping into her car at the valet stand.
Less than an hour earlier, and unbeknownst to Aniston, her ex-boyfriend John Mayer, 48, had exited the very same venue. The singer-songwriter was pictured alone, with a book tucked under his arm, dressed in a layered outfit of a black jacket over a pale blue shirt and grey cargo trousers. Representatives for both stars have been contacted by The Daily Mail for comment regarding the timing of their visits.
The History of an On-Again, Off-Again Romance
The brief overlap at the celebrity-favoured hotspot is a poignant echo of a past relationship. Aniston and Mayer were first introduced at an Oscars party in 2008 and dated on and off for approximately a year. Their romance bloomed just three years after Aniston's highly publicised split from first husband Brad Pitt, and while Mayer was cementing a reputation as a showbiz lothario, having previously dated stars like Jessica Simpson and Taylor Swift.
Their initial split in August 2008 was shrouded in conflicting narratives. Mayer told press he ended it "to be alone," while sources close to Aniston claimed she initiated the breakup, allegedly frustrated by his ties to the paparazzi and footing the bill for their lifestyle. The pair famously reconciled in time for the 2009 Vanity Fair Oscar Party, sharing a beaming, tight hug on the red carpet, only to part ways again weeks later.
In subsequent interviews, Mayer expressed regret, telling Playboy, "I’ll always be sorry that it didn’t last," and citing differences in their approach to fame and social media. Aniston, for her part, handled the split with grace, telling Vogue he remained a "wonderful guy" and that they still cared for each other deeply.
Moving On: New Love for Both Former Partners
Today, both stars have firmly moved on to new chapters. Aniston is now enjoying a blossoming relationship with Hollywood hypnotist and 'love guru' Jim Curtis, 50. The pair were first linked during a holiday in Mallorca in July 2023 and went public last September. Aniston has since praised Curtis as "extraordinary" and "kind," highlighting his work in helping people heal from trauma.
Meanwhile, John Mayer is rumoured to be dating 30-year-old TikTok star Kat Stickler. The pair were seen together in October 2023, and sources suggest Mayer is now in a place where he is "ready to settle down." This new relationship continues a pattern for Mayer, whose past girlfriends have often been significantly younger.
Despite their separate paths, the connection endures in subtle ways. Fans have long speculated that Mayer's 2009 song 'Edge of Desire' was written about Aniston, with its poignant lyrics about fear and longing. Furthermore, during the early 2020 COVID-19 lockdowns, Aniston showed there was no bad blood by joining Mayer's Instagram Live tribute to Bill Withers and laughing at his jokes.
This week's Sunset Tower incident serves as a mere footnote in their separate lives, a fleeting reminder of a past Hollywood narrative. Yet, it underscores how the echoes of a high-profile celebrity romance can resurface with a simple, coincidental timestamp at a legendary hotel bar.
