Jennifer Aniston is back on the market after her December 2017 separation from second husband Justin Theroux.
The “Morning Show” star said in September 2021 that she was looking for love again, though she insisted she wouldn’t turn to dating apps to find it.
“No one of importance has hit my radar yet, but I think it’s time. I think I’m ready to share myself with another,” she said in a SiriusXM interview.
After two public divorces (one of which involved a long-rumored cheating scandal) and several relationships with high-profile men, Aniston still has faith that there’s someone out there for her — just maybe not in Hollywood.
And while the “Friends” alum herself has debunked rumors that she and former co-star David Schwimmer were ever involved, she’s had quite the romantic history after all.
Page Six breaks down Aniston’s flings, boyfriends, husbands and everything in between below.
Charlie Schlatter
Aniston had a brief fling with ’90s teen heartthrob Charlie Schlatter.
The duo met on the set of the short-lived 1990 sitcom “Ferris Bueller,” which was based on the 1986 film “Ferris Bueller’s Day Off.”
GQ editor in chief Jim Nelson revealed in April 2014 that Aniston and Schlatter had “a brief, torrid romance — while playing, it must be said, his older sister.”
Their show ended after just one season, and their relationship apparently didn’t last much longer.
Schlatter eventually wed Colleen Gunderson in May 1994, and they have three children.
Daniel McDonald
Aniston’s first serious relationship was with the late Daniel McDonald.
The duo dated for five years in the early 2000s, with Aniston later citing the actor as the one who got away.
“He was my first love — five years we were together,” she told “Entertainment Tonight” in January 2015. “He would have been the one. But I was 25, and I was stupid. He must have sent me Justin [Theroux] to make up for it all.”
McDonald went on to marry film director Mujah Maraini-Melehi in 1999, and they had two kids. He died from brain cancer at age 46 in February 2007.
McDonald’s widow was not pleased with Aniston’s comments about her “first love,” telling “Inside Edition” (via Us Weekly), “Daniel and Jennifer had a relationship over 20 years ago, when they were both still very young. She made a life choice, but so did he.”
She continued, “I am sorry that Jennifer did not realize the treasure that was Daniel when she had the chance, long before he and I met and long before he died. It pains me to read the headlines that allude to her losing him tragically when in fact she was not present during his long and difficult illness.”
Yikes.
Jon Stewart
Jon Stewart seems to think he dated Aniston in the early ’90s, though she didn’t quite see it that way.
“I asked you out, and it was lovely,” the comedian reminded the actress on “The Daily Show” in August 2010. “I remember you brought so many of your friends. And I remember thinking, ‘She’s so excited to be on a date with me [that] she wants me to get to know her posse.’”
But Aniston replied, “If I remember correctly, wasn’t it sort of like, ‘Hey, a group of us are going out, do you want to join?'”
A classic mix-up indeed.
Stewart married Tracey McShane in November 2000, and they have been going strong ever since with their two kids.
Adam Duritz
The “Dumplin” star had a brief fling with Adam Duritz in 1995, but things apparently didn’t get too hot and heavy between the two.
The Counting Crows frontman admitted he didn’t know who Aniston was when they met and that their relationship only started because he was tricked by pals.
“A bunch of my friends lied to me and told me she had a crush on me,” he told “Entertainment Tonight” in July 2021, adding, “Those same friends lied to her and told her I had a crush on her.”
Still, Duritz only had nice things to say about Aniston: “She was really nice, really funny, really pretty, those were pretty good requirements for me, and also she liked me. It didn’t last very long, but she’s a nice girl.”
Duritz also reportedly said that they “never even slept together.”
He went on to briefly date her BFF and “Friends” co-star Courteney Cox.
Tate Donovan
Aniston moved on with actor Tate Donovan in 1995, but their relationship ended just over two years later.
Donovan memorably played a love interest of Aniston’s “Friends” character, Rachel Green, in five episodes, though the pair had already entered Splitsville in real life by that point.
Fortunately, Aniston gained a friendship while dating Donovan, revealing that he was the one who introduced her to gal pal Sandra Bullock.
“We were introduced by our former boyfriend. I say ‘our’ because you and I both partook of this one human being,” Bullock joked to Interview Magazine in February 2020, with Aniston replying, “Yes, we did. That’s a beautiful way of saying it.”
“He seems to have a type,” Aniston added before Bullock furthered that Donovan likes women who are “talented, funny, kind, introspective” and “generous.”
Donovan married writer Corrine Kingsbury in November 2005, but they divorced three years later.
Paul Rudd
Aniston was rumored to have dated Paul Rudd for several years, though the timeline remains unclear.
The duo appeared loved-up as they starred alongside each other in their 1998 film “The Object of My Affection.”
They continued to work on projects together, including “Friends” from 2002 to 2004 and 2012’s “Wanderlust.”
Eventually, Aniston came clean about having been romantically involved, reportedly joking that she and Rudd were “together when we were, like, 12.”
Rudd married Julie Yaeger in February 2003. They have two kids.
Brad Pitt
It seemed Aniston had finally found happiness in the late ’90s with none other than Brad Pitt.
The pair met in 1994, but it wasn’t until 1998 that they went on their first date after being set up by their agents, in true Hollywood fashion.
While they tried to keep their romance under wraps, the duo quickly became a tabloid favorite with the whole country watching their love grow.
In September 1999, they took their love public and made their red carpet debut at the Emmy Awards. Then, at a Sting concert that November, the pair announced that they were engaged.
The Hollywood sweethearts got married at a luxurious wedding ceremony in Malibu in July 2000.
Pitt then made an epic “Friends” cameo in 2001, playing one of Ross’ old high school friends who happened to despise Aniston’s character. Not only did the public enjoy seeing Aniston and Pitt together on the small screen, but the role earned him an Emmy nomination for Outstanding Guest Actor in a Comedy Series.
In February 2004, Aniston revealed that she wanted to start a family with the “Fight Club” actor, telling the Guardian, “It’s time. You know, I think you can work with a baby, I think you can work pregnant, I think you can do all of it. So I’m just truly looking forward to slowing down.”
But their plans to have children came to a screeching halt when the duo broke up in January 2005.
“We would like to announce that after seven years together, we have decided to formally separate,” they told the press in a joint statement. “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.”
Their split came amid rumors that Pitt had cheated on Aniston with his “Mr. & Mrs. Smith” co-star Angelina Jolie.
They finalized their divorce in October 2005, and while things were rocky for the exes for quite some time, they are back to being friends.
Pitt married Jolie in August 2014, but she filed for divorce in September 2016. While a custody battle between the parents of six still rages on, they were deemed legally single in April 2019.
Vince Vaughn
A hot commodity like Aniston doesn’t stay single for long, so it was no surprise that she quickly moved on from her messy breakup from Pitt with Vince Vaughn.
The duo dated for just a year, ending things in November 2006, but Aniston seemed grateful for their brief entanglement.
“I call Vince my defibrillator,” she told Vogue in December 2008. “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.”
Coincidentally, they starred as each other’s love interests in the 2006 movie “The Break-Up,” which was how their romance first started.
John Mayer
Many fans forget Aniston’s hot and heavy romance with John Mayer.
The pair met at an Oscars party in February 2008 and continued to date on and off until March 2010.
“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,” she told Vogue in December 2008 in the midst of one of their separations.
Apparently, the “New Light” singer had a much harder time accepting that their relationship didn’t work out, telling Rolling Stone in his February 2010 cover story, “I’ve never really gotten over it. It was one of the worst times of my life.”
Justin Theroux
Once again, Aniston found herself in the throes of heartbreak when things didn’t work out in her second marriage to Justin Theroux.
The stars met on set of the 2008 film “Tropic Thunder”; Theroux co-wrote the action-comedy, and it starred one of Aniston’s good friends, Ben Stiller. They worked together for the first time years later, co-starring in the 2012 movie “Wanderlust” — which also featured her ex Rudd.
Rumors that Aniston and Theroux were seeing each other began in May 2011 when they were spotted having dinner together, according to People, though reps at the time denied that their get-together was anything romantic.
They continued to make appearances together, all the while staying mum about whether they were together or not — though the writing was on the wall.
From the MTV Movie Awards afterparty in LA to a stroll in New York, they seemed inseparable, and Aniston even confessed she had a “new man” in June of that year.
In January 2012, the private couple took the next step in their relationship, snatching up a $24.9 million Bel-Air manse together, according to the Wall Street Journal.
That August, things took a serious turn when Theroux proposed on Aniston’s 41st birthday over dinner at Manhattan’s Blue Hill Restaurant.
She gushed over her new fiancé in July 2014, telling WWD, “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.”
A few years passed, leading many to wonder whether the stars would ever make it down the aisle, but then, they secretly tied the knot in August 2015 at their Bel-Air home. Sources told Page Six at the time that Aniston told people it was a surprise birthday party for Theroux to keep their nuptials a secret. Guests included Cox, Lisa Kudrow, Jason Bateman, Emily Blunt, John Krasinski, Sandra Bullock, Ellen DeGeneres and Portia de Rossi, and Jimmy Kimmel officiated the ceremony.
All seemed peachy for the pair aside from constant run-ins with the paparazzi and false rumors that Aniston was pregnant. She even spoke out about the lack of privacy they had, writing a blog post for the Huffington Post about being “harassed” daily by “aggressive photographers staked outside our home who will go to shocking lengths to obtain any kind of photo.”
As the couple continued to navigate marriage in the public eye, Aniston’s ex-husband, Pitt, announced his divorce from Jolie.
Theroux reacted to Brangelina’s breakup, telling Business Insider, “I’ll say this, [Jennifer’s] been in the public eye a very long time. I’ve been in the public eye not as long as it relates to this nonsense. But as a child of divorce, all I can say is that’s terrible news for those children.”
While they seemed like they were in it for the long haul, the duo announced in February 2018 that they were ending their marriage, saying they “decided to part ways as a couple” the previous December but looked “forward to continuing our cherished friendship.”
A source exclusively told Page Six at the time that they couldn’t make it work because he wanted to be in New York and she wanted to be in LA.
“Jennifer is more comfortable in Los Angeles with her close-knit group of friends,” the source explained, adding, “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 exes remain friends to this day.
