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Jennifer Aniston's whirlwind love life - 'pursued' by Harry Styles to Adam Sandler rumours

Irish Mirror logo Irish Mirror 16/03/2023 Katie Wilson

At 54, Jennifer Aniston is still one of Hollywood’s leading ladies – and one of the most eligible.

Since her split with second husband Justin Theroux in February 2018, the Friends star hasn’t gone public with a new man.

She was rumoured to have a secret boyfriend in 2021 and linked to her Morning Show co-star Jon Hamm, who recently got engaged to someone else.

Her latest love interest is said to be none other than singer Harry Styles, who is well known for his love of older women.

And while Jennifer recently confessed she isn’t on the lookout for husband number three, she is ready to be in a relationship again.

Jennifer Aniston bought Oprah's house © AFP via Getty Images Jennifer Aniston bought Oprah's house

“It would be wonderful to come home and fall into somebody’s arms and say ‘That was a tough day,’’she told Allure magazine.

Here we look back at Jennifer’s A-list love life, from new love rumours to two failed marriages, romances on the Friends set and her famous first boyfriend....

Harry Styles

Harry Styles © Getty Images Harry Styles

Could Jennifer have a new love interest for 2023 in the form of Harry Styles?

The 29-year-old singer is said to have been pursuing Jennifer, who he recently revealed was his first ever crush.

Their 'flirty' messages apparently started when Jennifer reached out to Harry after he suffered an embarrassing wardrobe malfunction and split his trousers in front of her during a gig in LA.

Since then Jennifer is said to have been joking with pals who she could get together with next – and it seems Harry could be on the list.

"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," an insider told Closer magazine.

Now Harry has split with ex-girlfriend Olivia Wilde, it could pave the way for him and Jen to get together....

Adam Sandler

Adam Sandler and Jennifer Aniston © NBCU Photo Bank via Getty Images Adam Sandler and Jennifer Aniston Jennifer Aniston, 53, gets cosy with co-star Adam Sandler © Instagram Jennifer Aniston, 53, gets cosy with co-star Adam Sandler

Jennifer sparked rumours she could be more than just friends with her Murder Mystery co-star Adam Sandler in early January after the pair were pictured cosying up during filming.

She even posted a New Year reel that heavily featured Adam and wrote alongside it: "Thanks 2022. 2023... ready, set, let's go. Happy New Year everyone!"

But it's no surprise Adam made such an appearance as he and Jen have been busy filming Murder Mystery 2, which is set in Paris and airs on Netflix on March 31.

The pair have actually been pals for years and Adam has been married to wife Jackie who he share two daughters with, since 2003.

Jennifer has previously said of their friendship: "You love each other, he takes you in and I'm very much the same way", adding they are like "family".

Justin Theroux

Jennifer Aniston and ex Justin Theroux © Getty Images Jennifer Aniston and ex Justin Theroux

Jennifer has been married twice, most recently to actor Justin Theroux who she split with in February 2018.

The pair first met in 2007 and friendship turned to romance when they both starred in 2011 movie Wanderlust a few years later.

2012 was a big year for the couple as they bought a house together, adopted a puppy and got engaged.

But the pair, who later said they 'felt married' for years, waited three whole years before tying the knot in a romantic ceremony in their backyard.

Despite seeming so happy together, Jen and Justin announced their shock split in 2018 after just two years of marriage.

In a joint statement they said: "This decision was mutual and lovingly made at the end of last year. We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship."

And proving you can stay friends with an ex, Jen and Justin have been spotted having dinner recently just as pals.

John Mayer

Jennifer Aniston and John Mayer (Pic:Getty) © Getty Images Jennifer Aniston and John Mayer (Pic:Getty)

Jennifer dated ladies' man John Mayer in the Noughties after they met at an Oscars party in 2008.

Their on-off romance was short lived and he later admitted to sleeping with 'four or five' other women while they were on a break.

They eventually parted ways in 2009 and John hinted their age gap - she is eight years older - was to blame.

"I'll always be sorry that it didn't last," he said at the time. "In some ways I wish I could be with her. But I can't change the fact that I need to be 32."

Vince Vaughn

Jennifer Aniston and Actor Vince Vaughn © Getty Images Jennifer Aniston and Actor Vince Vaughn

Shortly after her split with first husband Brad Pitt, Jen moved on with Hollywood hunk Vince Vaughn.

The pair met on the set of their appropriately titled movie The Breakup in 2005 and dated for a year.

Jen later told Vogue it was Vince who brought her back to life following her shock split with Brad.

She joked: "I call Vince my defibrillator. He literally brought me back to life... he was lovely and fun and perfect for the time we had together. I needed that."

Brad Pitt

Jennifer used to be married to Brad Pitt © Getty Images Jennifer used to be married to Brad Pitt Brad Pitt and Jennifer Aniston © FilmMagic Brad Pitt and Jennifer Aniston

Jennifer's most famous relationship is of course her five-year marriage to Brad Pitt.

The pair met in the early Nineties but didn't go on their first date until 1998 after reportedly being set up by their agents.

Two years later they tied the knot in a lavish ceremony in Malibu in July 2000, but by 2005 it was over.

It emerged Brad had become close to his Mr & Mrs Smith co-star Angelina Jolie, who Brad went on to marry, have children with and later divorce.

David Schwimmer

FRIENDS -- © NBCUniversal/Getty Images FRIENDS --

After her relationship with Brad broke down, rumours swirled that Jennifer and her on-screen love interest David Schwimmer were dating in real life.

At the Friends reunion they finally came clean, admitting they'd had a 'major crush' on each other during the first season of filming the show.

"We were both crushing hard on each other," David said, "but it was like two ships passing because one of us was always in a relationship and we never crossed that boundary. We respected that."

Confirming the feeling was mutual, Jen recalled telling him: "It's going to be such a bummer if the first time you and I actually kiss is going to be on national television."

"Sure enough, first time we kissed was in that coffee shop. So we just channelled all of our adoration and love for each other into Ross and Rachel."

Further pressed about how far they took their feelings, Jen later told DJ Howard Stern that: "No. I would proudly say I banged Schwimmer if that happened. But no."

Paul Rudd

Jennifer Aniston and Paul Rudd arrive at the premiere of Wanderlust © AFP Jennifer Aniston and Paul Rudd arrive at the premiere of Wanderlust

He might have joined Friends as Phoebe Buffay's boyfriend-turned-husband Mike Hannigan, but it was Jen who apparently used to hook up with Paul Rudd in real life.

The two are rumoured to have embarked on a brief romance - just before she met Brad Pitt - when Paul played her gay best friend in 1998 movie The Object of My Affection.

They later starred as a couple in 2012 movie, Wanderlust.

Asked whether or not it was weird to kiss onscreen, Jen joked, "Nah. I've kissed him for years," and Paul quipped: "We've made out for decades."

Tate Donovan

Jennifer and Tate dated before she starred in Friends © NBCUniversal Jennifer and Tate dated before she starred in Friends Jennifer and Tate dated before she starred in Friends © WireImage Jennifer and Tate dated before she starred in Friends

Jennifer was splitting up with actor Tate Donovan, who she had been dating for three years, when he joined the cast of Friends as her love interest.

Tate played Rachel's hunky Bloomingdale's client Joshua, who she ended up dating on the show.

The pair remain friendly to this day and say working together while they were breaking up even helped them deal with their split.

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