Inside Jennifer Aniston's Dating History

A look back at all the stars with whom she's been more than 'Friends.'

Jennifer Aniston is one of the most beloved stars around, so it makes sense that over the course of her adult life, she's been pretty irresistible to a bevy of Hollywood hunks.

The Morning Show actress has been married twice, to actors Brad Pitt and Justin Theroux, and has been linked to several other showbiz suitors. While her romances have been the stuff of tabloid fodder for decades, the star maintains a healthy outlook on relationships as a whole.

"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," she said in 2018. "When the work has been put in and it doesn't seem that there's an option of it working, that's okay. That's not a failure. We have these clichés around all of this that need to be reworked and retooled, you know? Because it's very narrow-minded thinking."

Back in 2008, after she'd split from Pitt but before she met Theroux, she similarly said, "I feel like I've been unbelievably lucky in love,. It just might not look the way it's supposed to look at this point."

Preach! Get to know Jennifer Aniston's husbands and dating history and find answers to the most burning questions about her love life.

Related: Jennifer Aniston's Net Worth Is So High, She Could Definitely Afford Monica's Friends Apartment Now!

Who is Jennifer Aniston's husband?

The star is happily single at the time of this writing. Though each of her two unions ended in divorce, she sees no reason to paint them as failures.

"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 didn't exist within that arrangement anymore," she once told Elle. "Sure, there were bumps, and not every moment felt fantastic, obviously, but at the end of it, this is our one life."

Aniston has also said that she's still open-minded to finding love... just not on a dating app.

"I'm going to just stick to the normal ways of dating," she told PEOPLE in June 2021. "Having someone ask you out. That's the way I would prefer it." That said, she's in no rush to tie the knot again, explaining, "It's not on my radar. I'm interested in finding a fantastic partner and just living an enjoyable life and having fun with one another. That's all we should hope for. It doesn't have to be etched in stone in legal documents."

Related: Brad Pitt's Dating History and Marriages

Did Jennifer Aniston date David Schwimmer?

Don't we all wish? But alas, Aniston's lobster is not Friends co-star David Schwimmer. The pair were rumored to be an item after an August 2021 report said they were spotted on dates at her favorite winery in Santa Barbara, Calif., and that Aniston had hosted Schwimmer for dinners at her home. However, Schwimmer's rep said there was "no truth" to the romance rumors.

That said, maybe they're just "on a break!" and it could still happen someday? After all, they used to have the hots for each other!

On HBO Max's Friends reunion in May 2021, Schwimmer and Aniston confessed to having major mutual crushes while playing on-again-off-again couple Ross Geller and Rachel Green, and that they used their real-life, ill-timed affection to make their onscreen love feel all the more real.

"The first season I had a major crush on Jen," Schwimmer said. "And I think we both, at some point, 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."

Aniston replied, "It was reciprocated! I remember saying at one point to David, 'It's going to be such a bummer if the first time you and I actually kiss is gonna be on national television!' Sure enough, the first time we kissed was in that coffee shop. So we just channeled all of our adoration and love for each other into Ross and Rachel."

Related: Jennifer Aniston, David Schwimmer Romance Rumors Are Swirling Around the Internet, But Is It Really True?

Did Jennifer Aniston date Paul Rudd?

Aniston once told GQ about fellow ageless wonder Paul Rudd, "I've kissed him for years," but that's just because the platonic pals also frequently star opposite one another onscreen. (In real life, Aniston has said that Rudd actually once dated her producing partner when they "were like, 12.") They've appeared together not just on Friends (where he played Phoebe's eventual husband, Mike), but also shared top billing in two rom-coms, 1998's The Object Of My Affection and 2012's Wanderlust, where Aniston met future husband Theroux.

Related: The Many Onscreen Loves of Paul Rudd

Did Jennifer Aniston date Ben Affleck?

Nope, although Aniston is one of the few mega-famous Jennifers who's never been linked to the Argostar. Ben Affleck is married to Jennifer Lopez after they were previously engaged from 2003 to 2004; he was also married to Jennifer Garner from 2005 to 2018 and shares three children with her. However, Aniston and Affleck did play a romantic couple in the 2009 rom-com He's Just Not That Into You.

Related: Like Us, Matt Damon Hopes Bennifer Is Back On: 'That Would Be Awesome'

Did Jennifer Aniston date Charlie Schlatter?

Aniston starred in the short-lived 1990 sitcom Ferris Bueller (based on the movie Ferris Bueller's Day Off), during which she briefly dated co-star Charlie Schlatter. The pair reportedly had a "torrid" romance, with Aniston playing Schlatter's big sister on the 13-episode series.

Who was Jennifer Aniston's first love?

In 2015, Aniston revealed to The New York Times that an unnamed man she dated before she became famous may have been the love of her life.

"He was my first love—five years we were together," she said, noting that her ex later passed away from brain cancer. "He would have been the one. But I was 25, and I was stupid." It was later revealed that the man was television actor Daniel McDonald, and his widow didn't take kindly to Aniston waxing poetic about their past.

Related: Almost More than Friends! David Schwimmer and Jennifer Aniston Reveal They Used to Crush Hard on Each Other

Did Jennifer Aniston date Counting Crows' Adam Duritz?

Counting Crows singer Adam Duritz had a brief romance with Aniston in 1995. They didn't last, and he later went on to date Friends co-star Courteney Cox in 1997 after she appeared in the band's "A Long December" music video.

Was Jennifer Aniston engaged to Tate Donovan?

Jennifer Aniston and Tate Donovan<p><a href="" rel="nofollow noopener" target="_blank" data-ylk="slk:Kevin.Mazur/Getty Images;elm:context_link;itc:0" class="link ">Kevin.Mazur/Getty Images</a></p>
Jennifer Aniston and Tate Donovan

Kevin.Mazur/Getty Images

Aniston dated Tate Donovan for three years from 1995 to 1998. The couple got engaged but didn't make it down the aisle. When Donovan appeared for a six-episode arc as Aniston's love interest Joshua on Friends, they were actually going through their split.

“I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time,” Donovan told Us Weekly. “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.” He added, “It was just six episodes. I mean, only because we were breaking up. We were like, ‘Hey, can we not keep doing this? ‘Cause this is really painful and 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.”

Related: Jennifer Aniston’s Net Worth Is So High, She Could Definitely Afford Monica’s Friends Apartment Now!

Did Jennifer Aniston marry Brad Pitt?

Jennifer Aniston and Brad Pitt<p><a href="" rel="nofollow noopener" target="_blank" data-ylk="slk:Jon Kopaloff/Getty Images;elm:context_link;itc:0" class="link ">Jon Kopaloff/Getty Images</a></p>
Jennifer Aniston and Brad Pitt

Jon Kopaloff/Getty Images

Shortly after her split from Donovan in 1998, Brad Pitt was likewise fresh off a broken engagement from Gwyneth Paltrow. Their agents set them up on a date, and the pair quickly became a full-fledged golden couple, tying the knot in 2000 with a blowout $1 million wedding. They were together for five years and shocked the entire world when they announced they were divorcing in 2005.

They said in a joint statement at the time, "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."

Pitt was almost immediately linked to his Mr. And Mrs. Smith co-star Angelina Jolie, with whom he went on to share six children and married in 2014. (Pitt and Jolie divorced in 2016.)

Were Jennifer Aniston and Vince Vaughn married?

Jennifer Aniston and Vince Vaughn attend the men's final of the French Tennis Open at Roland Garros Arena, in Paris, France on June 11, 2006.<p><a href="" rel="nofollow noopener" target="_blank" data-ylk="slk:Marc Ausset-Lacroix/Getty Images;elm:context_link;itc:0" class="link ">Marc Ausset-Lacroix/Getty Images</a></p>
Jennifer Aniston and Vince Vaughn attend the men's final of the French Tennis Open at Roland Garros Arena, in Paris, France on June 11, 2006.

Marc Ausset-Lacroix/Getty Images

Talk about art imitating life! Following her breakup with Pitt, Aniston dated Vince Vaughn after working with him on the 2006 rom-com The Break-Up. (The year before—i.e. the year Aniston and Pitt announced their split—Vaughn had co-starred with Pitt and Jolie in Mr. and Mrs. Smith.)

There was speculation at the time that Aniston and Vaughn got engaged, but they never confirmed those rumors (or really, any rumors about their romance). "Vaughniston" remained as low-key as they could, but split in December 2006. She told Voguein 2008, "I call Vince my defibrillator. He literally brought me back to life... 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."

Related: Friends With Money! Jennifer Aniston, Courteney Cox and the Rest of the Cast’s Sky-High Salaries for the Series

Did Jennifer Aniston date John Mayer?

Jennifer Aniston and John Mayer at the 2009 Vanity Fair Oscar party<p><a href="" rel="nofollow noopener" target="_blank" data-ylk="slk:Gregg DeGuire/Getty Images;elm:context_link;itc:0" class="link ">Gregg DeGuire/Getty Images</a></p>
Jennifer Aniston and John Mayer at the 2009 Vanity Fair Oscar party

Gregg DeGuire/Getty Images

Following her rebound romance with Vaughn, Aniston dated John Mayer on and off from early 2008 through March 2009. Their first split was a messy one, with Mayer telling reporters, "I'm the a**hole. I burned the American flag. I basically murdered an ideal."

Aniston (who's roughly a decade older than Mayer) was incredibly empathetic and kind towards Mayer in the aftermath, telling Vogue,  "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. But I feel seriously protective of him and us. Trust me, you'll never see that happen again from that man. 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 realize, we maybe need to do something else, but you still really, really love each other. It's painful. There was no malicious intent. I deeply, deeply care about him; we talk, we adore one another. And that's where it is."

They attended the 2009 Oscars together and posed on the red carpet, but they split for good not long afterward. Mayer admitted to Rolling Stone in 2010 of their breakup, "I've never really gotten over it. It was one of the worst times of my life."

How did Jennifer Aniston meet Justin Theroux?

Jennifer Aniston and Justin Theroux attend the 2017 Vanity Fair Oscar Party<p><a href="" rel="nofollow noopener" target="_blank" data-ylk="slk:JB Lacroix/Getty Images;elm:context_link;itc:0" class="link ">JB Lacroix/Getty Images</a></p>
Jennifer Aniston and Justin Theroux attend the 2017 Vanity Fair Oscar Party

JB Lacroix/Getty Images

Aniston technically met Theroux for the first time in 2007, but it wasn't until they reconnected on the set of 2010's Wanderlust that they became an item. Theroux popped the question that August, and three years later, they got married in a secret backyard wedding with a star-studded guest list. Jimmy Kimmel officiated the ceremony, Howard Stern gave a toast and attendees included John KrasinskiEmily BluntCourteney CoxLisa KudrowEllen DeGeneres and Portia de Rossi.

Related: 15 Best Jennifer Aniston Movies, Ranked

In late 2017, the pair separated, but they didn't announce their breakup until February 2018. "In an effort to reduce any further speculation, we have decided to announce our separation. This decision was mutual and lovingly made at the end of last year," they said in a joint statement. "We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship. Normally we would do this privately, but given that the gossip industry cannot resist an opportunity to speculate and invent, we wanted to convey the truth directly. Whatever else is printed about us that is not directly from us, is someone else's fictional narrative. Above all, we are determined to maintain the deep respect and love that we have for one another."

Indeed, they are still pals: In August 2021, Aniston shared happy birthday wishes for Theroux in her Instagram Stories (including a shirtless snap).

Did Jennifer Aniston and Brad Pitt get married again?

Brad Pitt and Jennifer Aniston attend the 26th Annual Screen Actors Guild Awards at The Shrine Auditorium on Jan. 19, 2020.<p><a href="" rel="nofollow noopener" target="_blank" data-ylk="slk:Emma McIntyre/Getty Images;elm:context_link;itc:0" class="link ">Emma McIntyre/Getty Images</a></p>
Brad Pitt and Jennifer Aniston attend the 26th Annual Screen Actors Guild Awards at The Shrine Auditorium on Jan. 19, 2020.

Emma McIntyre/Getty Images

Pitt and Aniston have never gotten back together, although the world hoped for a Brad and Jen reunion after their sweet moment backstage at the 2020 SAG Awards. Can you blame them? They were adorable!

They also were lauded for their chemistry at the live Fast Times at Ridgemont High table read, but Aniston and Pitt really are just platonic pals.

“It was absolutely fun. Brad and I are buddies, we're friends,” Aniston later told Stern about the table read (via PEOPLE). “And we speak, and there's no oddness at all, except for everyone that probably watched it and was wanting there to be, or assumed there to be. We had fun, and it was for a great cause.”

What was Jennifer Aniston and Gerard Butler's relationship?

Gerard Butler and Jennifer Aniston attend "The Bounty Hunter" premiere on March 11, 2010, in London. <p><a href="" rel="nofollow noopener" target="_blank" data-ylk="slk:Anthony Harvey/Getty Images;elm:context_link;itc:0" class="link ">Anthony Harvey/Getty Images</a></p>
Gerard Butler and Jennifer Aniston attend "The Bounty Hunter" premiere on March 11, 2010, in London.

Anthony Harvey/Getty Images

Aniston and Gerard Butler were rumored to be dating while promoting their film The Bounty Hunter in 2010, though neither confirmed a relationship. Butler did reveal that Aniston was a better kisser than Jolie, with whom he co-starred in Lara Croft Tomb Raider: The Cradle of Life.

Next, check out these 30 stunning throwback photos of Jennifer Aniston through the years!