They’re both world-famous celeb icons who have had their fair share of high-profile romances. And – despite a 25-year age gap – insiders say that a romance could be on the cards for Jennifer Aniston and newly single pop star Harry Styles.
Jen, 53, has been single since splitting from her second husband, Justin Theroux, in 2017, following two years of marriage. Meanwhile, Harry, 28, parted ways with director and actress Olivia Wilde, 38, last November after nearly two years together.
And last week, fans went into meltdown after Harry split his trousers on stage in front of Jennifer, who was reportedly sitting in the front row at his concert in LA. During a particularly energetic performance of his hit Music For A Sushi Restaurant, the star’s brown leather trousers ripped, and he was forced to protect his modesty by grabbing a Pride flag from the audience.
Fans online were quick to pick up on the fact that Jen had watched, with one posting, “Did Harry know Jennifer Aniston was there and that he ripped his pants right in front of her?” However, pals close to the former Friends star reveal that she used the comedy moment as a chance to start a flirty exchange with the star.
The source says, “Jen had been joking with pals about who she could get together with next and there has been talk about Harry. He ticks all the boxes – he’s successful, intellectual, edgy and cooler than almost anyone else out there. He’s totally in her league.
“Plus, of course, he’s clearly into older women and has admitted he had a crush on her growing up, so she’s confident this has a lot more chance of working out than some of her other recent matches.
“The way Jen sees it, she’d be crazy not to have some fun. Harry’s got a great sense of humour and is totally chilled, they’re a great match on paper. After the trousers incident, she got in touch, and it’s been quite flirty!”
Jen has had a roller-coaster love life since rising to fame in 1994. She was one half of Hollywood’s “It” couple when she married Brad Pitt in 2000, but they split after five years, with Brad later marrying his Mr & Mrs Smith co-star Angelina Jolie.
She then went on to date Vince Vaughn, John Mayer and Bradley Cooper, before marrying her partner of four years, actor Justin, in 2015. But the pair split two years later.
Meanwhile, Harry hit headlines for dating late X Factor host Caroline Flack a year after he starred on the show in 2011. He then dated Taylor Swift, Kendall Jenner and Camille Rowe. But his longest relationship has been with Olivia, who cast him in her film Don’t Worry, Darling in 2020. The following January, the pair raised eyebrows when they were pictured as wedding dates during Harry’s manager Jeffrey Azoff’s nuptials in California, and Harry – who is 10 years Olivia’s junior – reportedly referred to her as his girlfriend in his speech.
Olivia – who slammed claims from her children’s former nanny that she had cheated on her ex-fiancé Jason Sudeikis with Harry – was spotted on several occasions supporting her boyfriend at his gigs and also Coachella festival. But sadly, the pair called it quits in November last year, with Olivia said to be “very much upset about the break-up”.
But it seems he’s long had a crush on Jennifer, with the 1D star admitting on The Ellen Degeneres Show in 2020 that Jen had been his first celebrity crush.
Eagle-eyed fans also noticed how the pair follow each other on social media, with Jen “liking” one of his photos in December. Our source says, “They have a bunch of mutual business pals and already had each other’s numbers, so after Harry split his pants on stage, Jen used that opportunity to get in touch with him. They’ve struck up a regular back and forth.”
Harry’s career has skyrocketed in recent years. As well as his thriving acting career – earning praise in Don’t Worry, Darling – his latest album hit number one and he’s currently on a sell-out world tour until July.
The source says, “Friends feel it’s only a matter of time before they meet up for a date, Jen is keen and Harry seems game. But he’s super busy with tour dates and other work. At the moment it’s a watch-this-space situation – but it’s looking good and Jen’s super excited at what the future holds.”