John Mayer And Jennifer Aniston's Relationship, First Met At An Oscars Party, Broke Up Twice

John Mayer is a renowned American singer, songwriter, and guitarist who has captivated audiences of all ages with his charm. From his very first studio album, Room For Squares, which he released in 2001, John found immense success, both commercially and critically. Following this, over the years, John went on to produce a number of hits, including Continuum (2006), Paradise Valley (2013), The Search Of Everything (2017), and Sob Rock, among others.

It is worth mentioning that while his music pulled at his listeners' heartstrings, his personality also attracted several recognisable names in the industry. Among them, one we remember most is his relationship with F.R.I.E.N.D.S. star, Jennifer Aniston. For the unversed, John Mayer and Jennifer Aniston started dating in early 2008 and had a short-lived romance. Now, over a decade later, John and Jennifer almost had an awkward run-in recently at the Sunset Tower in Hollywood. This left fans to wonder more about their relationship, from how it began to how it ended. If you are one of them, here's a look back at John Mayer and Jennifer Aniston's relationship.  

How did John Mayer and Jennifer Aniston’s relationship begin? 

With both John Mayer and Jennifer Aniston being A-list celebrities, they naturally met at a high-profile event for the first time, the Oscars party held in February 2008, to be exact. At the time, Jennifer had been divorced from her ex-husband, Brad Pitt, for 3 years and had just split from Vince Vaughn. On the other hand, John Mayer was rumoured to be dating Minka Kelly after his long-term romance with Jessica Simpson. This is why, when John and Jennifer later ran into each other a week after they first met, “that was that.” Despite the duo having a significant age gap, fans were eagerly rooting for the two to date, knowing they would make a wonderful couple. Soon, fans' wishes were fulfilled when John and Jennifer looked idyllic as they spent time together in Europe.

Not just this, the couple also went on vacation together to Miami, Orlando, and Mexico. Jennifer and John had no intention of hiding their relationship, as could be understood when they attended a wrap party for Jennifer's 2008 film, Marley & Me. Jennifer also took time out of her busy schedule to meet up with her boyfriend during John's U.S and U.K. tours. While John and Jennifer's relationship appeared to be going strong on the outside, they surprised everyone in August 2008 by breaking up. The singer-songwriter's fans might be aware that he is known to openly talk about his relationships, and his breakup with Jennifer was no different. When confronted by the press on the streets of New York City, he said: 

“It’s the most normal thing in the world. There’s no lying, there’s no cheating, there’s no nothing. People are different, people have different chemistry, different lives. You’re either a cheater or you break up, and I’m not the first one, I’m the second one. I ended a relationship to be alone, because I don’t want to waste somebody’s time if something’s not right.” 

However, John and Jennifer's breakup did not last for too long, and they soon found their way back to each other a few weeks later, in October 2008. According to reports, the duo were spotted dining out together in New York City. In the same month, they were caught by paparazzi cameras for the second time, celebrating John's birthday in Los Angeles, California. In November, John admitted to People that “it's really nice to have somebody in life have your back.” He claimed that Jennifer was someone who “just knows me.”  

How did John Mayer and Jennifer Aniston's relationship come to an end? 

In 2009, John and Jennifer were spotted a couple of times at the beginning of the year. In February 2009, John was by his girlfriend's side as she celebrated her 40th birthday. It was reported that the singer gave Jennifer a rather special gift, a song he wrote only for her. The duo was also seen looking cosy together at the 2009 Oscar Awards. Unfortunately, in March 2009, they surprised everyone by breaking up for the second time. Although many wondered if they would get back together once again, it seemed that they had bid their goodbyes to each other for good this time. It is worth mentioning that neither John Mayer nor Jennifer Aniston spoke up about their breakup at the time. 

John Mayer and Jennifer Aniston almost had an awkward run-in with each other a decade after they split 

Even since their breakup, John Mayer and Jennifer Aniston have moved on with their love lives, dating different people over the years. Currently, The Morning Show actress seems to be in a relationship with a hypnotist named Jim Curtis. On the other hand, Jennifer's ex-boyfriend, John, was recently linked to TikTok star, Kat Stickler. While the former couple appeared to have an amicable relationship based on their past interactions, John and Jennifer almost ran into each other this week while visiting the Sunset Tower Hotel in Hollywood. Based on a report by the Daily Mail, they were only 40 minutes away from what could have easily been an awkward encounter, especially considering Jennifer's blossoming romance with Jim Curtis.  

What are your thoughts on John Mayer and Jennifer Aniston's relationship, as they almost avoided running into each other years after their breakup? Let us know.  

Also read: Who Is Timothy Busfield's Wife, Melissa Gilbert? All About The Actor Duo's Decade Long Relationship

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