Throughout her life, the Friends alum Jennifer Aniston has been linked to a few popular faces from the world of entertainment including the Once Upon a Time in Hollywood star Brad Pitt and The Leftovers actor Justin Theroux.
In the past, Aniston even got married twice but things just didn’t work out between her and her significant other at the time. Read on to learn everything about her past relationships.
Let’s take a trip down Jennifer Aniston’s flings, boyfriends, ex-husbands, and everything in between
Jennifer was first romantically linked to 90s teen heartthrob Charlie Schlatter. The two of them met on the set of the short-lived 1990 sitcom Ferris Bueller. The show was based on John Hughes’ film Ferris Bueller’s Day Off. Soon afterward, they sparked dating rumors.
In April of 2014, GQ editor-in-chief Jim Nelson disclosed that Charlie and Jennifer had a brief fling back in the 1990s. Around the time, he said, Aniston and Schlatter had “a brief, torrid romance — while playing, it must be said, his older sister.”
The show Ferris Bueller came to an end just after one season. Meanwhile, the whirlwind romance of the pair also didn’t last long. Shortly soon, Charlie moved on in his life and he went on to marry Colleen Gunderson in May 1994. The couple shares three kids.
The Just Go With It actress’ first serious relationship came with Daniel McDonald. During an interview with Entertainment Tonight in January 2015, Jen called Daniel her ‘First Love’ and she talked about the pair’s romance and said, “He was my first love — five years we were together.”
Aniston further added, “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.” Jen and McDonald called it quits after dating for a total of five years in the early 2000s. Daniel went on to marry film director Mujah Maraini-Melehi in 1999. The pair had two kids. He passed away at the age of 47 due to brain cancer in February of 2007.McDonald’s widow was not happy with Jennifer’s comments on her first true love. In an interview with Us Weekly, she said, “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.”
Mujah 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.”
There’s a classic mix-up when it comes to Jon and Jennifer’s relationship. The standup comic thought that he dated the Dumplin’ actress in the early ’90s, though she didn’t quite see it that way.
“I asked you out and it was lovely,” Jon reminded Aniston on The Daily Show in August 2010. He went on to say, “I remember you brought so many of your friends. And I remember thinking, ‘She’s so excited to be on a date with me, she wants me to get to know her posse.’”
On the other hand, Jennifer recalled the incident in a completely different light. The Office Christmas Party actress said, “If I remember correctly, wasn’t it sort of like, ‘Hey, a group of us are going out, do you want to join?’”
Jon got hitched to Tracey McShane in November 2000 and the two of them have been together ever since then. The couple has two kids.
Jennifer dated the Counting Crows frontman briefly in the year 1995 but maybe they were not meant to be together. Adam stated that he didn’t know Aniston when the two of them met for the first time and he was tricked by his friends to start dating the actress.
During an interview with Entertainment Tonight in July 2021, Duritz said, “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.”
Despite the fact that their romance didn’t last, Adam had only good things to say about Jen. He told the media outlet, “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.”
The musician also revealed that they “never even slept together.” After their breakup, he went on to date her BFF and Friends co-star Courteney Cox.
The Marley & Me star moved on in her life with actor Tate Donovan in 1995. Their romance came to an end after two years together. Tate played the role of a love interest of Jennifer’s character Rachel Green in Friends for a total of five episodes.
In an interaction with Us in September 2018, the Argo actor spilled the beans on his relationship with Aniston. At that point, he said, “I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time.”
Donovan further added, “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.” Tate got married to writer Corrine Kingsbury in November 2005 but they ended up getting divorced three years later.
The Object of My Affection costars were rumored to be dating for several years. They worked together on many projects including the 1998 film The Newton Boys, the hit show Friends from 2002 to 2004, and 2012’s Wanderlust.
Eventually, Jennifer revealed that the two of them were seeing each other at one point. She jokingly added that the pair were “together when we were, like, 12.” Later on, Rudd married Julie Yaeger in February 2003. The couple shares two kids.
It looked like Jennifer finally found her soulmate in the late ’90s and it was none other than Brad Pitt. The pair crossed paths in the year 1994 and they began dating in 1998. For their first date, they were set up by agents in true Hollywood fashion.
The Switch actress and the Mr. & Mrs. Smith star tried to keep their romance away from the flashing cameras. Within the blink of an eye, the two of them became fan favorites and the whole country was keen to see their love blossom.
Aniston and Pitt made their romance official in September 1999. They made their red carpet debut at the Emmy Awards. Soon afterward, the couple was spotted together at a Sting concert that November, where they confirmed they were engaged.
Brad and Jennifer got married in 2000
The Hollywood sweethearts tied the knot at a luxurious wedding ceremony in Malibu in July of 2000. Back in the day, Brad also did a great cameo in Friends. He essayed the role of one of Ross’ old high school friends.
The fans of the show enjoyed watching Jen and Pitt on the small screen together. For his performance in the sitcom, he even bagged an Emmy nomination for Outstanding Guest Actor in a Comedy Series.
In a 2004 interview with The Guardian, Jennifer stated that she wanted to start a family with The Lost City actor. She told the media outlet, “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 maybe destiny had some other plans for the pair. The couple parted ways in January 2005. At that time, they issued a joint statement to the press that read, “We would like to announce that after seven years together, we have decided to formally separate.”
They further added, “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 breakup saw the light of the day amid rumors that Pitt had cheated on Aniston with his Mr. & Mrs. Smith co-star Angelina Jolie. Jen and Brad’s divorce got finalized in October of 2005. Then, things maybe have turned rocky for the former flames but now they are good friends.
Pitt went on to marry Angelina Jolie in August of 2014 but she filed for divorce from him in September 2016. They share six kids. They were declared legally single in April 2019.
Jen got back in the dating game with Wedding Crashers actor Vince Vaughn. The duo dated for a year before calling it quits in November 2006 but Aniston was still glad for their brief entanglement.
During an interaction with Vogue in December 2008, the Cake actress said, “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.”
Let’s us tell you a bizarre coincidence, these two played each other’s love interests in a 2006 movie together titled The Break-Up, which was exactly the way their romance ended.
The Love on the Weekend singer and the He’s Just Not That Into You actress had an on-again, off kind of relationship. The two of them first met at an Oscars party in February 2008 and they continued to date till March 2010.
While speaking to Vogue in 2008, Jennifer talked about her relationship with the singer. Then, the duo was in the middle of one of their separations. She said, “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.”
However, in his February 2010 cover story, the You’re Gonna Live Forever in Me singer told Rolling Stone, that he had a harder time accepting the fact that he and Jennifer couldn’t make things work. He said, “I’ve never really gotten over it. It was one of the worst times of my life.”
Jennifer and Justin met each other for the first time on the sets of the 2008 film Tropic Thunder. Theroux co-wrote the action-comedy, and Jennifer’s good friend Ben Stiller was also a part of the film. The two of them worked together for the first time in the 2018 film Wanderlust.
Aniston and Justin co-starred in the movie and her ex-boyfriend Paul Rudd was also featured in it. According to People, the romance rumors of Jen and Justin began swirling in the air in May 2011 when they were spotted having dinner together. Soon afterward, they were snapped together on multiple occasions but they stayed tight-lipped about their relationship status. They didn’t clear the fact that they were dating each other or not.
The pair went public with their relationship at the 2011 MTV Movie Awards. From there on these two were inseparable. In June of that year, Jen even revealed that she had a new man in her life. As per the Wall Street Journal, they took their romance to the next level in January 2012 by purchasing a $24.9 million Bel-Air manse together.
In August of that year, their fairytale romance took a serious turn when Justin popped the big question to Aniston on the occasion of her 41st birthday over dinner at Manhattan’s Blue Hill Restaurant.
In a 2014 interview with WWD, Jennifer couldn’t stop gushing over her new fiancé. She said, “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.”
Jennifer and Justin secretly tied the knot in 2015
Their fans were just pondering when will these two walk down the aisle. Aniston and Theroux secretly got married in August 2015 at their Bel-Air home. At that point, close sources told Page Six, that Jennifer told people it was a surprise birthday party for Theroux to keep their nuptials a secret.
Their wedding was a star-studded affair as it was attended by many A-listers including Lisa Kudrow, Courteney Cox, Jason Bateman, Emily Blunt, John Krasinski, Sandra Bullock, Ellen DeGeneres, and Portia de Rossi. The talk show host Jimmy Kimmel officiated their wedding ceremony.
All things seemed to be working out just right for these two. The only thing that was a bit concerning for them was the constant run-ins with the paps and the rumors that Jennifer was pregnant. While penning down a blog post for the Huffington Post, Aniston talked about the lack of privacy the pair had then.
Jennifer spoke about being “harassed” daily by “aggressive photographers staked outside our home who will go to shocking lengths to obtain any kind of photo.” Aniston and Justin navigated through their marriage in the spotlight. After a while, the news of Aniston’s ex-boyfriend Brad and his then-wife Angelina Jolie’s split came out.
In an interview with Business Insider, Theroux put out his thoughts on Brangelina’s breakup and said, “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.”
We thought Jennifer and Justin were in it for the long haul but that’s not how things ended for these two. In February of 2018, they announced 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.”
Then, a close source told Page Six, that they couldn’t make it work because Theroux wanted to be in New York whereas Aniston wanted to live in Los Angeles.
The insider told the media outlet, “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.” They continue to remain friends to this day.
At the end of the day, we just want Jennifer Aniston to be happy in life. It doesn’t matter if she’s single or committed it’s her own choice. We wish her nothing but the best of everything.
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