A Timeline Of The Ups And Downs Of Jennifer Aniston's Love Life

Jennifer Aniston is a successful actor and beloved icon, who's often been perceived as the ultimate "girl next door" and "America's sweetheart," as she once told The Times. After becoming a household name in the '90s, she's managed to remain relevant since "Friends" went off the air, gracefully making the notoriously difficult pivot from television to film and then back to gracing our screens with award winning TV. But "The Morning Show" star is more than her long career or the many trophies she's nabbed — and, since Aniston's fame has meant that she's under constant scrutiny, she's also more than the tabloid gossip about her relationships. 

In 2016, Aniston wrote about the pressures and frustrations of dealing with the press and paparazzi for HuffPost: "If I am some kind of symbol to some people out there," read her poignant commentary, "then clearly I am an example of the lens through which we, as a society, view our mothers, daughters, sisters, wives, female friends and colleagues." Indeed, Aniston has found herself turned into an ideal following her rise to fame, when many imitated her iconic hairstyle, "The Rachel" (via Biography), and envied her seemingly perfect romances.

Nowadays, this aspirational figure has two divorces under her belt and is, as some might say, surprisingly single. Rather than manifesting marriage No. 3, Aniston told InStyle that she's focused on being "a happy, content, fulfilled human being." But it took a few decades to get there — here's a timeline of the ups and downs of Jennifer Aniston's love life.

Inside Jennifer Aniston's short-lived romance with Charlie Schlatter

Jennifer Aniston's first onscreen acting appearance was as a dancer on "Mac and Me" in 1988, and the 19-year-old didn't even get a credit. But it didn't take long for her to land a recurring role as Jeannie Bueller on the 1990 TV show, "Ferris Bueller." Though the spinoff series only lasted one season, it helped launch Aniston's career — as well as her first public relationship. While the original, mega-popular 1986 film, "Ferris Bueller's Day Off," starred Matthew Broderick, the sitcom version cast Charlie Schlatter in the titular role. Both appearing in all 13 episodes of the short-lived series, Aniston and Schlatter reportedly struck up an on-set romance quickly.

In an exclusive Hollywood exposé written for GQ in 2014, former show assistant Jim Nelson (and subsequent fly on the wall) revealed that Aniston was extremely affable on set, and that her relationship with Schlatter was public knowledge to the entire cast and crew. "Everyone on set thought she was hot," he divulged, "including Schlatter, with whom she had a brief, torrid romance — while playing, it must be said, his older sister. To we immaturions on the show, this seemed extra-hot. Like performative incest." 

The series was cancelled part-way through its single season, and Aniston's romance with Schlatter seemingly petered out, but her own career went on to much greater heights — presumably and partly due to the likability and charm she exhibited on the set of "Ferris Bueller."

She revealed that Daniel McDonald 'would have been the one'

When Jennifer Aniston speaks about her "first love" (via The New York Times), she's referring to fellow actor Daniel McDonald, who found success on Broadway after their 1990 to 1994 relationship ended, just before her "Friends" fame took off. According to Playbill, the Tony-nominated star, who appeared in musicals like "Steel Pier" and "High Society," sadly died of brain cancer at age 46 in 2007. 

Speaking with Rolling Stone in 1999, Aniston called her former boyfriend of five years "just wonderful" and "a dear friend." She later shared a hint of regret for letting him go during her 2015 interview with The Times. "He would have been the one. But I was 25, and I was stupid," Aniston, who was engaged to Justin Theroux at the time, lamented. "He must have sent me Justin to make up for it all."

Per sources cited by the Daily Mail, Aniston reportedly never "got over letting Dan slip through her fingers." But at the time of this death, McDonald was married to Mujah Maraini-Melehi, and his widowed wife wasn't pleased at the media circus that followed Aniston's comments to The Times. His name wasn't quoted in the original interview, but when McDonald's identity was revealed, Maraini-Melehi posted a disapproving message on Facebook (via the Daily Mail): "I am very upset that the media is exploiting Daniel's memory in connection to Jennifer Aniston. ... It pains me to read the headlines that allude to her losing him tragically when she was not present during his long and difficult illness."

The Friends star dated Counting Crows singer Adam Duritz

The same year she ended her relationship with Daniel McDonald in 1994, Jennifer Aniston went on to star as Rachel Green on "Friends," her breakout role and one of the most popular sitcoms of the decade. Almost immediately, the actor became a household name and the show earned numerous Emmy nominations in its first year. Fresh out of a long romance and ready to enjoy the central perks her success (sorry, we had to), Aniston had a short but exciting relationship with Counting Crows frontman Adam Duritz in 1995. 

Duritz was also enjoying the fruits of his band's labor following two Grammy nods in 1994 — but instead of publicizing their relationship for the PR, these two kept their romance surprisingly private. The former couple's mutual pal, photographer Randall Slavin, took one of the scarce photos of the duo "hanging out" during this time. "'Friends' had just exploded and was massive, and Adam was in the biggest band in the country and his record was blowing up," Slavin explained to InStyle. "So they were the biggest power couple."

They had met at Los Angeles' The Viper Room through connections, but Duritz had missed the "Friends" fervor, so he barely knew who she was. "A bunch of my friends lied to me and told me she had a crush on me. Those same friends lied to her and told her I had a crush on her," Durtiz told ET in 2021. He added, "It didn't last very long, but she's a nice girl."

The awkward romantic and co-working timeline of her relationship with Tate Donovan

Despite her ever-increasing popularity and rising status as one of the most famous faces in Hollywood, Jennifer Aniston found herself dating people in the industry who weren't familiar with "Friends." Clueless about the scale of her fame, fellow actor Tate Donovan's surprise at the constant paparazzi that swarmed Aniston briefly drove him away when they first got together in 1995, per E!. A few weeks later, however, they resolved to try again. Subsequently, the couple lasted three years, regularly made tabloid headlines, and even got engaged by 1997, with Aniston gushing to People that she had "always been somebody that really wants to be married" and calling Donovan the "perfect guy."

Unfortunately, "The O.C." actor would not be the person to fulfill Aniston's wedding fantasies, as the two broke up in 1998 ... right when Donovan landed a role as her on-screen love interest, Joshua, on "Friends." Um, awkward. The six-episode stint made for good TV, but it wasn't the most enjoyable filming experience for these two, and the situation tested their acting skills. 

"I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time," Donovan later reflected to Us Weekly. "And, so that was tricky to sort of act and act like we were 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."

Jennifer Aniston and her rumored relationship with Paul Rudd

In 1998, Jennifer Aniston starred alongside Paul Rudd in the film, "The Object of My Affection," which sees the single and pregnant Nina (Aniston) fall in love with her gay best friend, George (Rudd). No stranger to on-set romances (or on-screen breakups), Aniston was rumored to have briefly dated Rudd while filming, per Cosmopolitan. The enduring speculation has followed the pair for years — and their continual work together and clear on-screen chemistry has only spurred it forth: In 2002, Rudd landed the recurring character of Mike Hannigan, Phoebe's eventual husband, on "Friends," and a decade later, he and Aniston were cast as an on-screen married couple in the movie, "Wanderlust." 

However, while they insist that things never got romantic in real life, the two have professed their mutual love over social media on birthdays and the like ... but just as friends. When GQ asked whether it was awkward for the two pals and longtime co-stars to share an on-screen kiss in 2012, Aniston quipped, "Nah. I've kissed him for years." For his part, Rudd joked, "We've made out for decades."

How Jennifer Aniston met Brad Pitt

Jennifer Aniston and Brad Pitt were indisputably one of the most iconic celebrity couples of their time, and were the definition of Hollywood royalty after they started dating in 1998. Aniston was at her peak on "Friends," and Pitt had already established himself as a screen star powerhouse with a Golden Globe win and an Oscar nomination under his wing. But the duo first met briefly, prior to gaining mutual superstardom, through their managers in 1994, who eventually set them up four years later.

Despite their admittedly very Hollywood beginnings, Aniston's reason for loving Pitt from the get-go was deeper. "He was just this sweet guy from Missouri, you know? A normal guy," she told Rolling Stone in 2001, adding that "he just disarms you immediately." Of falling in love during their first date, Aniston later told Diane Sawyer, "It was weird. ... That was a really easy evening. It was really fun."

By 2000, she and Pitt shared a very public relationship and got hitched in a giant wedding. Though they didn't have any children together, these two stars did share a baby of sorts: their production company, Plan B Entertainment. The couple embarked on the venture together in 2001, and the passion project worked until their marriage didn't, as they'd separated right as it was coming to fruition. According to The Hollywood Reporter, Aniston is no longer involved in the project — a casualty of what would end up being a painful, publicized divorce.

Did Brad Pitt cheat on Jennifer Aniston?

In January 2005, Brad Pitt and Jennifer Aniston announced their split to People: "We have decided to formally separate. ... We happily remain committed and caring friends with great love and admiration for one another." After Pitt's steamy role in "Mr. & Mrs. Smith" alongside Angelina Jolie, rumors began swirling that the future Brangelina was the culprit. In an attempt to rebuff these claims, the statement continued, "Our separation is not the result of any of the speculation reported by the tabloid media."

Of course, the ensuing relationship between Pitt and Jolie — culminating in children, marriage, and then a divorce of their own — did nothing to quell the hearsay and tabloid headlines. Aniston was left to process the split publicly. In February 2004, she had told The Guardian that it was "time" for her and Pitt to have a baby, saying she was "looking forward to slowing down." But by July 2005 — just a few months after she officially filed for divorce – the infamous Rockwell-esque W magazine shoot, "Domestic Bliss," was released, starring Pitt and ... Jolie. Wrestling with the sudden divorce and ongoing suspicions of infidelity, Aniston said of the shocking spread to Vanity Fair, "There's a sensitivity chip that's missing." For his part, Pitt has long denied the cheating allegations, maintaining that these relationships didn't overlap.

Aniston has since made peace with the divorce, and she and Pitt eventually made their way back to being friends. "I don't regret any of it," she said, adding, "We helped each other through a lot, and I really value that."

Jennifer Aniston and her cathartic romance with Vince Vaughn

During a 2001 interview with Vanity Fair, Jennifer Aniston exposed how her marriage with Brad Pitt had excavated her own issues about coming from a broken home. Five years later, she revealed how her own divorce had aggravated the wounds, but told the same outlet, "You can't let the devastation of a divorce take over and win — let it make you this bitter, closed-off, angry, skeptical person."

She seemed to be taking her own advice when she got together with Vince Vaughn in the summer months of 2005. Having been grieving the end of her marriage, Aniston told Vogue in 2008 that Vaughn "literally brought [her] back to life," explaining, "He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course."

Their seemingly cathartic relationship began on the set of "The Break-Up," a 2006 comedy of errors about a breakup which ends up bringing a couple together — both on-screen and in real life. However, there were strains that eventually made the two grow apart, and Aniston and Vaughn called it quits after a year and a half of dating. As Vaughn revealed in a 2015 interview with Playboy (via E!), the media circus around their romance — given that it was Aniston's first relationship post-Pitt — had unfortunately distracted from the actual relationship. The two stayed close, however, with Vaughn telling Parade in 2008 (via E!): "I have a real, genuine connection with Jen. ... That continues to this day."

She reportedly had a fling with Paul Sculfor

Jennifer Aniston's team announced her split from Vince Vaughn in a statement to People in December 2006: "Jennifer and Vince mutually agreed to end their relationship but continue to be good friends today." The amicable breakup meant that the "Friends" alum reportedly wasted no time getting into a new relationship — this one more short-lived. According to reports, Aniston started dating British model Paul Sculfor in 2007, engaging in a brief but passionate relationship. That June, a source alleged to Metro that Aniston had "left Paul in no doubt that he is the man for her," claiming, "She even let slip that he's better in bed than either Brad [Pitt] or Vince."

Sculfor may not have as recognizable a name as Aniston's other exes, but according to his agency, Select Models, he was considered "the original male Supermodel." He also earned the moniker, "the face that's worth a million dollars," on a 1997 cover of Attitude magazine. While he supposedly captured Aniston's eye for a few months 10 years later, the two apparently lacked compatibility, as they were at different points in their lives. According to a source cited by The Sun, "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." 

Indeed, while Aniston had resolved after her divorce to spend less time working and focus on her family (via Vanity Fair), Sculfor went on to date other A-List celebrities, like Cameron Diaz, per Marie Claire.

Inside Jennifer Aniston's tumultuous relationship with John Mayer

John Mayer has a reputation for being one of Hollywood's most notorious heartbreakers, but as Jennifer Aniston told Vogue in December 2008, "It isn't designed. Love just shows up and you go, 'Oh, wow, this is going to be a hayride and a half.'" This on-and-off couple certainly lived up to that expectation. 

Mayer was first linked to Aniston that February after meeting at an Oscars party. In a role reversal from her earlier dating years, she "barely knew his music" at the time, but told the outlet, "Then we ran into each other a week later, and that was that." But their relationship was turbulent, and the requisite swarms of press and paparazzi would eventually be this celeb romance's demise by March 2009, as a string of public outbursts and infamous interviews from Mayer — who's eight years Aniston's junior — made their final breakup messy. "I've never really gotten over it," he told Rolling Stone. "It was one of the worst times of my life." However, Mayer denied to Playboy that some songs from his subsequent "Battle Studies" album were about Aniston (via Billboard).

Par for the course, Aniston had nothing but compassion for her ex, who'd made it known he was the one who broke up with her. "I feel seriously protective of him and us. It's painful. There was no malicious intent," she told Vogue. "I deeply, deeply care about him; we talk, we adore one another. And that's where it is."

Did she rekindle her alleged romance with Gerard Butler?

Reportedly lured back into another on-set romance, Jennifer Aniston supposedly got together with Gerard Butler after starring opposite him in the 2010 rom-com, "The Bounty Hunter," in which Butler plays a bounty hunter who finds himself on a long journey trying to bring his ex, Aniston's character, to court. The movie wasn't the biggest hit among critics and audiences alike, but its combination of slapstick comedy and tender romance was held together by the duo's on-screen chemistry. In real life, that spark reportedly remained and — you guessed it — dating rumors began swirling, per Us Weekly.

Aniston gushed about Butler to Access Hollywood during the press tour, saying (via People), "We just had so much fun [making the movie] together. ... He's just fun. Gerry's the most unpretentious guy." However, while Us Weekly reports that the two actors "laughed off relationship speculation," the hearsay was renewed in 2020, when Aniston and Butler were spotted together and rumors of a rekindled romance flew. According to a source cited by Star Magazine (via Micky), "Things started slowly, with some Zoom calls and texts and that led to a series of meetups at Jen's house. It's all on the down-low, and that's a big part of the fun."

All that said, it looks as though this blast from Jennifer Aniston's alleged dating past either ended quickly, or it simply never existed in the first place.

Jennifer Aniston married Justin Theroux

In 2011, Jennifer Aniston found what she had been looking for: someone to settle down with. The "Friends" alum met actor-writer Justin Theroux through mutual friend Ben Stiller on the set of his 2008 movie, "Tropic Thunder," which he and Theroux wrote together. However, it took a few encounters before the connection manifested in a relationship, as Aniston's first impression of Theroux wasn't the best. "I remember thinking he was very dark," she told PopSugar, adding, "At first you think he could be like a serial killer, but he is actually the nicest person in the world."

It wasn't until the pair met again in 2011 to film "Wanderlust" that romantic sparks began to fly. That August, the two shacked up and started living together, per People. Ever concerned about his privacy, Theroux didn't reveal much, once saying (via Marie Claire), "I understand the curiosity, but other than saying I am happy, I am not going to indulge it." Aniston was similarly tight-lipped, but expressed her confidence and clarity in the relationship to InStyle: "As I get older, I realize what qualities are important in love and what suits me. And what I won't settle for." 

So, it wasn't too shocking when the two got engaged in 2012 and married in three years later in a surprise star-studded affair officiated by late-night host Jimmy Kimmel — though Aniston and Theroux pretended the event was just a backyard birthday party for the latter to keep the paparazzi away, per People.

Then she divorced Justin Theroux

For a while, Jennifer Aniston and Justin Theroux seemed like the perfect couple. However, their marriage lasted two and a half years before the duo released a shocking separation statement to the AP in February 2018, which emphasized that they were "two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship." 

Despite their admitted desire to quell rumors before they began and keep the matter private, many wondered if part of the reason for the split was their seemingly opposite lifestyles. Aniston was invested in their California life and newly renovated home, previously telling Architectural Digest, "I look around at my husband and my dogs and our home, and there's nowhere else I want to be." Yet, some insiders claimed that Theroux wanted to be in New York City. Though Aniston was born and raised in the city, the lack of privacy reportedly made the lifestyle tough. "Justin can hop on his [motorcycle] ... without being bothered," a source alleged to ET, "but for Jen, the paparazzi are all over her."

After the split, Theroux did move back to the Big Apple and divulged the details of the divorce only sparingly. "It was heartbreaking ... only in the sense that the friendship would not be the same," he told The New York Times. Thankfully, the two have continued to keep their "cherished friendship" alive, with Theroux telling Esquire in 2021, "We don't talk every day, but we call each other. We FaceTime. We text."

Jennifer Aniston is enjoying being single

Following her divorce from Justin Theroux, Jennifer Aniston has apparently been enjoying the single life. According to a source cited by Us Weekly, she reportedly needed some time alone and didn't want to rush into anything new after divorce No. 2. But unfortunately, Aniston's period of reflection didn't stop the tabloids from inventing rumors about her love life. From stories about her reuniting with old flame Brad Pitt to striking up a romance with former "Friends" costar David Schwimmer, Aniston can't seem to escape tabloid gossip. "It's pretty crazy," she told InStyle in August 2018. "The misconceptions are 'Jen can't keep a man,' and 'Jen refuses to have a baby because she's selfish and committed to her career.'" 

Despite this unwanted attention from the press, Aniston is content with her life. Her hit Apple TV+ Series, "The Morning Show," has garnered her success — she even snagged a SAG Award for her work — and she described herself as "a very fortunate and blessed human being" who's "in a really peaceful place" to People in June 2021. But will Aniston be dipping her toes back into the dating pool anytime soon? Well, as she confirmed to InStyle, she's not interested in online dating — not even Raya, the exclusive celebrity dating app.

Aniston, who admitted that marriage is "not on [her] radar" and that she's just "interested in finding a fantastic partner," told People, "I'm going to just stick to the normal ways of dating. Having someone ask you out. That's the way I would prefer it."