Jennifer Aniston is an undeniable showbiz icon and has been in the public eye for over 30 years, having earned her first regular TV role back in 1990 with Molloy. Following that, her role in the hit sitcom Friends turned her into a household name, as did her subsequent film career.
Being such a beloved, famous figure, Jennifer’s dating life has always been a major topic of discussion for fans. That’s why, when the actress was spotted wearing a huge diamond ring on her fourth finger at both the SAG Awards and the People’s Choice Awards last week, people started wondering if it could mean that she was planning to walk down the aisle for a third time.
But, if Jennifer Aniston is currently in a relationship, she’s keeping it well under wraps and hasn’t spoken publicly about her latest beau. So, whilst everyone speculates as to Jennifer’s current relationship status, we’re taking a trip down memory lane with a deep dive on the actress’ star-studded dating history. And we mean star-studded…
2021 (almost): David Schwimmer
To the delight of Friends fans, their mini reunion for an Uber Eats Superbowl ad had fans reminiscing for the a time when Ross and Rachel were almost a thing IRL.
During the Friends reunion episode which aired in May 2021, both David Schwimmer and Jennifer Aniston admitted to having had crushes on each other during filming.
Speaking with James Cordon, David revealed, ‘At some point, we were crushing hard on each other, 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.’
Jennifer added, ‘Honestly, I remember saying one time to David, “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.
‘We channelled all of our adoration and love for each other into Ross and Rachel.’
No wonder Ross and Rachel were consistently named the public’s top couple year after year when Friends was airing.
2011-2018 - Justin Theroux
Jennifer Aniston’s second husband was actor Justin Theroux (The Girl on the Train) – the cousin of beloved British documentary maker and podcast host Louis Theroux.
Jennifer and Justin originally met on the set of Tropic Thunder in 2007, despite neither of them starring in the film. Justin wrote the screenplay for the satirical action comedy and Jennifer came to set one day to support her pal Ben Stiller who was directing. From there a strong friendship was formed, but the pair didn’t start dating until they began working together on Wanderlust in 2011.
Then, in 2012 Jennifer and Justin took things to the next level when they bought a $24.9millon mansion in Bel Air together and began living together.
The pair got engaged in August 2012 on Jennifer’s 41st birthday and they tied the knot in a secret ceremony three years later on 5 August 2015, in front of A-list royalty including Jennifer’s BFFs Courtney Cox, Lisa Kudrow, Jason Bateman and Sandra Bullock as well as Emily Blunt and John Krasinski. The ceremony was officiated by late night talk show host Jimmy Kimmel.
Apparently Jennifer and Justin told friends and family that they would be attending a small celebration for Justin’s 43rd birthday, but it turned out to be the pair’s wedding. The newly-wed couple then headed off on their honeymoon to Bora Bora.
In 2014 Jennifer took the opportunity to gush about her then-fiancé Justin saying in an interview, ‘He’s just so beautiful and handsome to me, and I love that his eyeballs are so beautifully captured because those eyes just knock me out every day. He just gets better every year. He’s just like a lost gem in the sand, and he’s just always been there and been brilliant.’
Sadly however, in February 2018 the duo announced their divorce with a joint statement. It read, ‘We have decided to announce our separation. 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.’
Whilst neither Justin nor Jennifer have ever spoken about the reason for their split, reports at the time claimed that Justin struggled with life in LA and preferred to spend the majority of his time in New York.
Page Six reported, ‘Jennifer is more comfortable in Los Angeles with her close-knit group of friends, but Justin doesn’t feel as at home in LA, nor with Jennifer’s friends. He loves New York and the edgier crowd in the city.’
The pair have remained close friends since their split however and were even spotted having dinner together in April 2023 with Jason Bateman and his wife Amanda Anka.
After their split Justin admitted, ‘I would say we’ve remained friends. We don’t talk every day, but we call each other. We FaceTime. We text. Like it or not, we didn’t have that dramatic split, and we love each other.
‘I’m sincere when I say that I cherish our friendship. We can not be together and still bring each other joy and friendship. Also, she makes me laugh very, very hard. She’s a hilarious person. It would be a loss if we weren’t in contact, for me personally. And I’d like to think the same for her.’
Whilst Jennifer hasn’t spoken specifically about her and Justin’s divorce, she did give a rare insight into her dating life in 2019 sharing, ‘My marriages, they've been very successful, in [my] personal opinion. And when they came to an end, it was a choice that was made because we chose to be happy, and sometimes happiness doesn't exist within that arrangement anymore.
She continued, ‘Sure, there were bumps, and not every moment felt fantastic, obviously, but at the end of it, this is our one life and I would not stay in a situation out of fear. Fear of being alone. Fear of not being able to survive. To stay in a marriage based on fear feels like you're doing your one life a disservice.’
2010 - Harry Morton
Prior to her relationship with Justin Theroux, Jennifer Aniston apparently went on a few dates with restaurateur and founder of the restaurant chain Pink Taco, Harry Morton, despite the 12-year age difference between them. At the time Jennifer was 41 whilst Harry was 29.
A source told People at the time, ‘Harry has been to Jen’s Beverley Hills house and they have had several restaurant dates as well. Just like Jen, Harry is a dog lover and they both love the beach.’
Their dalliance didn’t last long. Sadly, Harry passed away in November 2019 after suffering a sudden cardiac arrest.
2009 – Gerard Butler
Many assumed that Jennifer Aniston and Gerrard Butler were dating after they looked cosy whilst promoting their film The Bounty Hunter in 2009, however the pair never confirmed or denied the rumours.
Gerard’s constant gushing about Jennifer in interviews did nothing to slop the rumours either, and he hasn’t slowed down to this day…
Speaking on The Drew Barrymore Show in August 2023, the Scottish actor reminisced about filming with Jennifer admitting, ‘She is the coolest chick on the planet – she’s so great to work with, fun, down-to-earth, humble, and it was such a joy just playing these scenes with her.’
2009 – Bradley Cooper
After starring in He’s Just Not That Into You together, Bradley Cooper and Jennifer Aniston apparently had a brief summer fling in 2009.
The pair have remained close friends however and reunited last weekend to present Barbra Streisand with an SAG Life Achievement Award.
2008-2009 John Mayer
Jennifer Aniston and singer John Mayer met in early 2008 at an Oscars party and proceeded to date on and off for a year before officially ending in March 2009.
Despite famously dating a much younger woman himself with Taylor Swift, John seemed to attribute his and Jennifer’s split to their eight-year age gap saying in an interview with Playboy the following year, ‘I’ll always be sorry that it didn't last. In some ways I wish I could be with her. But I can't change the fact that I need to be 32.’
‘One of the most significant differences between us was that I was tweeting. There was a rumour that I had been dumped because I was tweeting too much. That wasn’t it, but that was a big difference.’
He continued, ‘The brunt of her success came before TMZ and Twitter. I think she’s still hoping it goes back to 1998. She saw my involvement in technology as courting distraction.’
Jennifer however was nothing but class when she responded to his comments in an interview with Vogue. She said, ‘He had to put that out there that he broke up with me. And especially because it's me. It's not just some girl he's dating. I get it. We're human.
‘And it doesn't take away from the fact that he is a wonderful guy. We care about each other. It's funny when you hit a place in a relationship and you both realise, we maybe need to do something else, but you still really, really love each other. It's painful.’
She continued, ‘There was no malicious intent. I deeply, deeply care about him; we talk, we adore one another. And that's where it is.’
2007 – Paul Sculfor
Jennifer Aniston briefly dated British model Paul Sculfor for several months in 2007, but it never developed into anything serious.
A source at the time said, ‘There was chemistry, but the truth is that Jen wants to settle down with a reliable man and start a family. Paul travels a lot and is constantly surrounded by beautiful women.’
The hottie – who has worked with brands like Giorgio Armani, Versace and Valentino – also dated some other big Hollywood names including Cameron Diaz and Lisa Snowdon before marrying socialite Federica Amati in 2016.
2005-2006 - Vince Vaughn
Jennifer Aniston and actor Vince Vaughn met whilst filming The Break-Up in Chicago and were first linked together when they were spotting looking cosy during the movie’s wrap party in the September.
In October 2006, Jennifer’s rep announced that the pair had split saying, ‘Jennifer and Vince mutually agreed to end their relationship but continue to be good friends today.’
Their close friendship was confirmed in 2008, when Jennifer said of their relationship - which came shortly after her split from Brad Pitt, ‘I call Vince my defibrillator. He literally brought me back to life. My first gasp of air was a big laugh! It was great.
‘I love him. He's a bull in a china shop. He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course.’
1998-2005 - Brad Pitt
Brad Pitt and Jennifer Aniston were originally set up by their agents in 1994, but it wasn’t until 1998 that the pair went on their first date.
From that moment on Jennifer and Brad’s relationship went from strength to strength. In September 1999 the pair made their red carpet debut at the 51st Emmy Awards and two months later they announced their engagement at a Sting concert.
Their dreamy, big-budget Malibu wedding occurred on 29 July 2000, taking place in front of 200 guests including Courteney Cox, Edward Norton, Salma Hayek and Cameron Diaz on a private estate. The ceremony was followed by a live performance by singer-songwriter Melissa Etheridge.
As is well-documented however, the pair announced their split in January 2005, shortly after Brad worked with Angelina Jolie - who he then went on to marry - on Mr and Mrs Smith.
Their official joint statement read, ‘We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media.
‘This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months.’
Speaking about their split and the rapidity with which Brad and Angelina began dating (lest we forget that infamous joint W Magazine photoshoot) in 2006, Jennifer admitted, ‘I can imagine Brad having absolutely no clue why people would be appalled by it.
‘Brad is not mean-spirited. He would never intentionally try to rub something in my face. In hindsight, I can see him going, “Oh—I can see that that was inconsiderate.” But I know Brad. Brad would say, “That’s art!” There’s a sensitivity chip that’s missing.’
Brad and Angelina eventually tied the knot in 2014, but their marriage came to a bitter end in 2016 when Angelina filed for divorce following an allegedly violent incident on a private plane.
In a report obtained by Entertainment Weekly, Angelina accused her then-husband of physical assault as the family returned from a two-week trip.
The actor allegedly grabbed Angelina by the head and shoulders and shook her while yelling, ‘You're f**king up this family’ before apparently punching the ceiling of the plane four times. Angelina also claims that Brad poured beer on her while she was under a blanket with the kids.
A vicious custody battle and difficult divorce proceedings have since ensued between Angelina and Brad.
Back to Jennifer and Brad however, appear to have remained friends - famously they were spotted chatting backstage at the 2020 Screen Actors Guild Awards, even holding hands at one point.
1998 – Paul Rudd
Paul Rudd and Jennifer Aniston were rumoured to have had a brief relationship that began after they both starred in The Object of My Affection.
The pair have kept tight-lipped on the rumours however whilst promoting their film Wanderlust in 2012, the duo were asked in an interview with GQ if it was ‘weird to kiss’ on screen, having been close for such a long time.
Jennifer hilariously responded, ‘Nah. I've kissed him for years,’ whilst Paul quipped, ‘We've made out for decades.’
When Paul was named Sexiest Man Alive by People magazine in 2021, Jennifer shared a sweet Instagram tribute to her pal saying, ‘This makes me so happy. We've always known this, but Paul Rudd is officially people's Sexiest Man Alive!’
1995-1998 - Tate Donovan
Jennifer Aniston and Tate Donovan began dating after they were introduced by mutual friends in 1995. Other than attending a few red carpet events together, their relationship was pretty low key until Tate was cast as Rachel Green’s love interest on Friends.
Sadly however, the reality was that the pair had been dating for over two years before Tate’s stint on the show and were in the middle of breaking up when they began working together.
In 2018 Tate admitted, ‘The only bummer was Jennifer and I were breaking up at the time. And so that was tricky to sort of act, and act like we are just meeting each other, and falling in love, or whatever, interested in each other, when we’re sort of breaking up. That was just tough.’
‘The people that know that we dated think that we met on Friends. But in fact we had dated for two years before then, and it was over by the time we were on Friends together.’
Before he began dating Jennifer, Tate was in a relationship actress Sandra Bullock and it was actually through Tate that Jennifer and Sandra became close friends.
In a joint interview in February 2020, the pair confirmed this with Sandra saying, ‘We were introduced by our former boyfriend. I say "our" because you and I both partook of this one human being.’
Jennifer replied, ‘Yes, we did. That’s a beautiful way of saying it. He seems to have a type,’ to which Sandra responded, ‘Women who are talented, funny, kind, introspective and generous.’
There were rumours that Jennifer and Tate got engaged in 1997, but just months after the rumours started swirling Jennifer told People, ‘There's nothing to report. You have to take more time to get to know someone.’
Jennifer and Tate eventually broke up in 1998.
1995 - Adam Duritz
Jennifer Aniston and Counting Crows frontman Adam Duritz briefly dated in 1995 after meeting at The Viper Room, a nightclub in West Hollywood.
Speaking about their short-lived romance in 2021 Adam said, ‘She was nice, really funny, really pretty. Those are pretty good requirements for me and also she liked me. [It] didn't last long.’
Adam then went on to date Jennifer’s BFF and Friends co-star Courteney Cox two years later after the actress starred in the band’s music video for A Long December.
1990-1995 - Daniel McDonald
Seeing as it occurred before she became a household name in Friends, not much is known about Jennifer Aniston and Daniel McDonald’s relationship although in 2015, Jennifer told The New York Times, ‘He was my first love. Five years we were together. He would have been the one, but I was 25 and I was stupid.’
In February 2007 Daniel sadly passed away at the age of 46 after a battle with brain cancer.
1990 – Charlie Schlatter
Jennifer Aniston’s first public relationship was with actor Charlie Schlatter.
Whilst working on a TV adaptation of Ferris Bueller’s Day Off, Jennifer and Charlie had a ‘brief, torrid romance’ – according to former GQ Editor in Chief Jim Nelson who worked as an assistant on the show. A little bit awkward considering Jennifer was playing Charlie’s older sister…
Daisy Hall is a News and Entertainment writer on Grazia, specialising in TV and film meaning that you can count on Daisy for the latest (and best) recommendations.