The (Boy)Friend Zone: A Complete Timeline of Jennifer Aniston’s Dating History

The public knows Jennifer Aniston as the glamorous, likable, humorous, and beautiful celebrity she is today but the early years weren’t always so easy for the actress. Jen said she was on the chubby side and was bullied in school.

She seems so down-to-earth today because she did not forget where she came from. Although she is the daughter of famous actor John Aniston, Jen still earned her allowance by doing chores like cleaning toilets and later worked as a waitress. She learned the value of hard work and shed off any awkwardness. Her bullies must be speechless today!

Jen has admitted to having dyslexia and struggling with it as a child in school. However, she didn’t realize she was dyslexic until she was diagnosed in her early twenties. Finally, her past struggles made sense although the psychological damage was done. “I thought I wasn’t smart”, she confessed. “I just couldn’t retain anything”.

She’s further admitted that reading actually is not one of her preferred pastimes because of her dyslexia. This could present challenges for an actress who needs to learn scripts. But this learning disability was another struggle Jen overcame before she even knew what it was.

Of course, almost everyone knows Jennifer Aniston from “Friends” but who can forget her in “The Object of My Affection”, “Marley and Me”, “Friends with Money” and loads more?

But her very first time on-screen was actually an uncredited role in the film “Mac and Me” where she played a dancer at Mcdonald's. She admitted that her most embarrassing role was in the bizarre horror movie “Leprechaun” where she played the teenager who discovers an evil leprechaun living in her basement. Perhaps not her luckiest role, but clearly it only got better from there for Jen’s career.

Jen has always seemed to have a lovely relationship with her father, the late John Aniston, but her relationship with her mother, Nancy Dow was quite strained. Dow was an actress and former model who, according to Jen, had high, superficial expectations for her daughter. She has stated that her mother “was very critical” of her and that she held “petty” grudges.

Their relationship disintegrated further after Dow released a book titled “From Mother and Daughter to Friends” and gave an interview in which she was critical of her daughter. Although damaging, Jen eventually overcame the hurt caused by her mom.

Jen admitted to being bullied as a kid for her weight and, unfortunately, the scrutiny of the public eye wouldn’t end there. Early on in her career and before entering into her years on-set in “Friends”, the young actress was told to lose around 30 pounds. She was even told she wasn’t landing roles because she was “too heavy”.

She went on to lose said pounds and, although she has been in fantastic shape ever since and advocating for a healthy lifestyle, she has always resented the way women in Hollywood are criticized for their weight and appearance.

As a very young actress, Jen listened to her agents, making sure she looked the way casting agents wanted her to. But, as she got older, she got more and more exasperated by the constant superficial scrutiny women in Hollywood faced.

About 20 years after her breakthrough, she was featured as a guest writer for the “Huffington Post” and boldly spoke against this scrutiny. She also sounded off on how women have expectations of marriage and motherhood thrust on them and how these standards are simply not a one-size-fits-all. Jen’s boldness only made fans fall more in love with her.

Therapy is gradually becoming a more socially acceptable route to better mental health. Despite her strength and resilience in life, Jen isn’t one to turn down professional help, especially when it comes to some of her past painful experiences.

She was candid about attending therapy sessions in the past to help her with her difficult relationship with her mother. But it’s also helped her in multiple spheres of life. “I’ve really gotten a lot out of therapy”, the actress admitted. Jen has said that therapy has also helped her with anxiety and to thrive while being in the public eye.

Dating can put your life on display, and when relationships don’t work out, it can make your personal life feel pretty shaky. But imagine if you were a celebrity! Like many celebrities, Jennifer Aniston likes her privacy — something that’s very hard to have as an actress. And she would certainly like privacy —especially when it comes to her dating life.

Over the decades, Jen’s love life has been the subject of many tabloids, especially some of her most heartbreaking times. But she has remained strong through all of it, refusing to let public opinion dictate her personal life.

In many of her roles, Jennifer Aniston has played the woman who gets the man in the end. Unfortunately, the same cannot be said about her personal life. Over the years, Jen has had a lot of relationships but none of them have lasted.

Jen certainly hasn’t let her career suffer because of anything in her personal life but she also hasn’t given up on love. Despite her heartbreaks, the actress and spokeswoman still believes that she can find love in her life. We have to admire her vulnerability and strength!

Although Jennifer Aniston has had her share of romantic relationships over the years, she’s also been a major celebrity crush for many-including other celebrities. Can you guess which famous names have had a crush on America’s sweetheart?

KJ Apa and Cole Sprouse from the show “Riverdale” have admitted to having a little thing for the charming actress and so have Ashton Kutcher and Jake Gyllenhaal. It’s clear that Jen has quite an effect on people. Kutcher even went so far as to ask Jen out on a date when she was married to Brad Pitt!

Co-star romances typically bring lots of publicity, but unfortunately, they often fizzle out pretty quickly. So who was the lucky man to first be by the side of Jennifer Aniston? Well, while she was starting out in the spotlight at least, it was fellow-actor Charlie Schlatter.

The two met on a short-lived TV adaptation of “Ferris Bueller’s Day Off '' and played siblings on the show. Off-set, Aniston and Schlatter dated for a short time in 1990 and, although it was not the greatest romance of her life, Charlie Schlatter will forever be known as Jen’s first boyfriend.

There are actually few details about Jen’s romance with co-star Charlie Schlatter. Apparently, almost everyone on the set thought Jen was hot stuff, especially Schlatter. It was a bit awkward that she was playing his sister on the show, but off-set apparently things could really heat up.

Their show didn’t last and neither did their romance, although they did date for four years. Schlatter later married Colleen Gunderson, with whom he shares three kids, and Jen moved on to launch her career as Rachel Green on “Friends”.

This next fling of Jen’s was nearly entirely off of the public radar. When she was just 25 and just before stepping into the TV show “Friends”, Jen dated Daniel McDonald, a Tony Award-winning actor. He and Aniston dated for about five years before splitting for an undisclosed reason.

Tragically, McDonald passed away in 2007. Fans were surprised when Jen made a dramatic remark saying that McDonald “would have been ‘the one’ if she hadn’t been “25” and “stupid”. Sounds like Daniel McDonald held a very special place in her life.

After Jen admitted (after many years) that she had a real connection with deceased Daniel McDonald, going so far as to say he may have been “the one”, she received some unexpected pushback. McDonald’s widow lashed out saying that Aniston wasn’t there when McDonald was battling the disease that took his life and that she was just trying to get publicity out of his death. Ouch.

Understandably, McDonald’s widow (Mujah Maraini-Melhi) would be upset that the media focused more on Jen’s relationship with the late McDonald than his actual untimely death. But Jen certainly didn’t have any ill intentions.

Truly an odd couple, Jen next dated “Counting Crows” singer Adam Duritz. Not much is known about the couple’s relationship, except that it started around 1995 as “Friends” was taking off.

At the time, Duritz said he really didn't know who Aniston was, and had never seen “Friends” but that his friends matched them, telling them both they were interested in each other when no such interest was initially expressed. The two dated for a brief time and, although it’s not really known why the two split, Duritz said “it didn’t last very long, but she’s a nice girl”.

At times, Jennifer Aniston and Paul Rudd seem to be male and female versions of the same person. Their similar personalities create great on-screen chemistry, but what about off-screen? Apparently, the two actors did briefly date but the romantic relationship never really blossomed.

Rudd eventually went on to marry Julie Yaeger (who used to work for his publicist) with whom he shares two kids. Jen and Rudd remain on congenial terms and even like “old friends”. And, there’s no denying the two actors are comedy gold on-screen which is certainly why they have appeared in more than one film together.

So, just how many times have Paul Rudd and Jennifer Aniston been on-screen together? Their first time appearing together on-screen was on none other than “Friends”. Rudd starred as Mike, Phoebe’s love interest on the show.

Jen and Paul also starred together in the 1998 film “The Object of My Affection” where her character falls for her openly gay friend (Rudd). They also starred together years later in the comedy “Wanderlust”. No matter what project Jen and Paul are working on together, you know big laughs are in store.

For Jen’s next romance, she got together with a fellow actor from “Friends”, Tate Donavan. For six episodes, Donavan played a love interest of Rachel's and also had a romance off-set. This would have been delightful for fans, but unfortunately for the couple, their professionalism and acting skills were soon heavily tested.

During the course of the six episodes where Donavan played Rachel’s love interest, their real-life romance began to unravel, leading to a breakup. But the two carried on as professionals and finished out the storyline. Her next romance, however, wouldn’t be as brief.

Obviously, Jennifer Aniston and Tate Donavan’s relationship had become very, very serious if the two were engaged. And, even though they broke off the engagement and the relationship, the two professionals continued their work on “Friends'' together, but that didn’t mean it was an easy or enjoyable time.

Tate admitted that he felt like he was “dying inside” while working on the set with his ex. It was so tortuous that, when they finally wrapped the last scene, Donavan went back to his trailer and cried. Sounds a bit traumatic. Now that’s a bad day at work!

Perhaps one of the most iconic celebrity couples, Jen and Brad Pitt were Hollywood royalty. And, of all her romances, any fans consider this her greatest, although Pitt didn’t end up being the man she deserved.

Jenn and Brad began dating in 1998 and were at the altar in the year 2000. They were married for five years until the marriage became rocky from rumors of Brad’s relationship with his “Mr. & Mrs. Smith” co-star Angelina Jolie. The two decided to split in 2005. Surprisingly, they remained on congenial terms, despite the supposed infidelity and their highly publicized divorce.

The two first met back in 1994 and, in an interesting twist, were set up by their agents. Depending on the power given to them, agents can act as guardians of both a celebrity’s career and also of personal matters that may be in their client’s best interest.

In this case, however, the two agents were friends and thought that the stars would hit it off. Yet perhaps, given that both Brad and Jen were rising stars, the agents may have also thought it’d be a great publicity move. And, at least at the beginning, the agents were right.

The celebrities officially began dating in 1998. Their pairing truly appeared to be a match made in Hollywood heaven. Although they tried to keep their relationship private for a time, they decided not to hide it anymore when they appeared on the red carpet at the Emmys in 1999.

Just later that year, the two were so head-over-heels for each other that, while attending a Sting concert, they took to the stage to announce that they were engaged! Jen made sure to give the audience a look at her stunning engagement ring. How’s that for an interruption?

Jen and Brad headed to the altar the following year in Malibu with paparazzi lurking outside the venue. The wedding was notable because the reception ended with a stunning fireworks display. After the wedding, the honeymoon phase seemed to last with the newlyweds making more red carpet appearances and with Jen sharing her long-term relationship advice with reporters.

While married, Brad even made a notable appearance on “Friends” playing a character who hated Rachel. Certainly an ironic casting. And sadly, as it seems most “Hollywood fairytale” romances turn out, their relationship was headed for a dead end.

People started suspecting something was shaky when Jen gave a certain interview. After the interviewer said that Brad Pitt was “the love of her life”, Jen responded with “is he the love of my life?”

She went on to say that he was a “big love” in her life but that she isn’t one to say “he’s the love of my life”. She then complimented Brad as someone who grounds her and really knows her. While some assumed that she is giving room in her life for the love of friends and family, a few red flags were raised.

From remarks like these, it appeared as though Jen and Brad’s relationship had begun to fall apart slowly. Despite hints at trouble between the two, in interviews, she continued to share how she and Brad were “meant to be” and of their plans of starting a family. She even gushed about how she hoped to travel with him in the future.

But internal trouble proved to be too much. And, from the outside, it appeared that Brad’s relationship with Angelina Jolie was what ultimately split the couple up. Brad and Jen announced their separation in January of 2005.

And where was Brad Pitt’s love life before he met Jennifer Aniston? Well, before these two got together, Brad had been connected to a number of women. As his career was beginning, he began dating Shalane McCall, who was 9 years his junior.

He then dated British singer Sinitta, actresses Robin Givens, Christina Applegate, Jill Schoelen, Juliette Lewis, Geena Davis, Julia Ormond, Thandie Newton, Claire Forlani, and Gwyneth Paltrow (before meeting Jennifer Aniston). Judging by some of the names on this list and his future relationship with Angelina Jolie, Brad must have a thing for his co-stars!

After Jen and Brad’s relationship ended, Brad moved on with Angelina Jolie. But what about Jen? She didn’t disappear from the spotlight or sink into depression, at least not for long. She moved forward. She admitted to Vanity Fair that after her divorce she was “lonely”, “upset” and “confused” (understandably) but that she wouldn’t let it keep her down.

She dove hard into growing and maintaining her friendships as well as a slew of films that only made her even more of a household name. Jen became a model for how to not let a breakup derail your personal progress.

These days, after all of the past drama and heartbreak, it seems that Jen and Brad have been able to leave the past behind. But, reportedly, it wasn’t always this way. Soon after their separation, Brad was openly in a relationship with Angelina Jolie, going so far as to appear with her in W Magazine.

Yet, years later and after his divorce from Angelina Jolie, fans were wide-eyed when Brad and Jen had a warm (and somewhat flirtatious) rapport between them. But "Braniston" fans can take comfort in knowing that the two are now just on very good terms.

Shortly after divorcing Brad, Jen moved on with Vince Vaughn. The two starred together in the comedy “The Breakup” (a bit ironic) and decided to give real-life romance a try. Because this was her first relationship after Brad Pitt, the new couple was hit with tons of publicity and public pressure.

The enormous pressure added additional stress to their new relationship. The two eventually broke up and Vaughn later admitted that the public pressure and publicity contributed to the tension that ended their relationship. Despite the pair not working out, they are said to still be on friendly terms.

Dating an A-lister like Jen was definitely not in the best interest of Vince's secretive side. Even though they broke up, Jen and Vince stayed on good terms. The two still chatted afterward and Vince even went to one of Jen’s birthday parties.

She confessed that Vaughn was her “defibrillator” after her painful divorce and that he had come into her life at just the right time. They laughed, they had fun together, but they decided that they were just not good as a couple, especially under the pressure of the spotlight and the paparazzi.

Many may not remember this very brief fling of Jen’s. The actress was seen with Paul Sculfor, a British model, after calling it quits with Vaughn. This “relationship” might have been classified as more of a “fling” as it didn’t last more than a few months.

According to those close to Jen, it was primarily because of Paul’s demanding modeling commitments that the two couldn’t take their relationship further leading to its dissolution. However, the pair did manage to avoid the paparazzi for the few months that they were together - a major win for anyone in the public eye!

Jen took a shot with another musician, this time with singer-songwriter John Mayer. The two met in 2008 at an Oscars after-party. Although Mayer was eight years Jen’s junior, the two clicked...for a time.

The relationship started to disintegrate later that year. Unfortunately for Jen, it was a highly publicized breakup and Mayer took little issue with sharing his side of the story with the media. Reportedly, it was Mayer who broke up with her but, in later interviews, the singer hints at regretting his decision. Despite the initial awkwardness after the breakup, the two are still friends.

John Mayer hasn’t been known for his great diplomacy and decorum. The singer-songwriter has been known to stick his foot in his mouth and then some when it comes to the press. He definitely threw out a verbal faux pas when it came to his breakup with Jen.

In speaking about the pain of the experience, Mayer said that when the couple broke up he “burned the American flag” and that he had “murdered an ideal”. Yikes. The controversial remarks gave him nothing but public scolding. Reportedly, Jen was also “really, really upset”.

Reports spread that Jen briefly and casually dated actor Josh Hopkins in 2010 after the two were introduced by Courtney Cox. It was soon after reported that the two had broken up and that Hopkins hadn’t treated her well. Specifically, that she had wanted a real relationship and he just wanted to date casually.

But, according to Hopkins, the two simply had a friendly dinner and that the rumors “spread like wildfire.” After denying the rumors and calling them “weird” and “hurtful” he confirmed that he and the actress were “just friends”.

These two looked fabulous on paper and in the public eye. Jen and Bradley both starred in “He’s Just Not That Into You”, although they never appeared together on-screen. Off-set, however, that was a different story.

The two actors dated for a short time but before he could make a serious commitment to Jen, the couple split and Bradley moved on with Rene Zellweger, making it seem that he, well, just wasn’t that into Jen. It seems that the two were better suited as friends. Although it was another romantic relationship that went sideways, it surely wasn’t Jen's last.

There were probably more than a few fans who would have loved to see Jennifer Aniston and Bradley Cooper together. With their thousand-watt smiles, sparkling eyes, and amicable personalities, they seemed like a great match.

They were together long enough to have been considered as having dated one another, but just how long did they date? It’s not really known how long they went out for, but it was reported that after the two connected at an event, they went out sometime in 2009. They were seen out together being very talkative and flirty. Unfortunately, it didn't last.

This was Jen’s second super-serious spotlight relationship. She met handsome actor Justin Theroux on the set of “Tropic Thunder”. Although Jen didn’t star in the film, her good friend Ben Stiller did and so, while visiting him on-set, she and Justin hit it off.

It’s unclear when exactly they began dating, but it was sometime during 2011. The two gradually made public appearances together and even co-starred in the romantic comedy “Wanderlust” in 2012. Justin had been in a very long-term relationship with a stylist named Heidi Bivens and it’s speculated they he may have left her for Jen.

Jen and Justin reportedly moved into a Bel-Air mansion together in 2011 sometime after they started dating. Jen revealed that, when she first met Justin, she thought he was “always so sweet” and “very nice”. As their relationship blossomed, she began introducing him into her group of friends, with the two of them hanging out with Courtney Cox, Reese Witherspoon, Jason Bateman, and Chelsea Handler.

The two even adopted a puppy together! The relationship escalated relatively quickly, with Justin proposing to Aniston in 2012, on his birthday. It looked like Jen had finally found the love of her life.

Fans must have found it romantic that Justin would ask Jen to marry him on his birthday (like giving himself the gift of marriage to her?). But after the huge ring was slipped onto her finger in 2012 the couple didn’t appear to set a date.

Two years passed during which their relationship appeared to still blossom, with the pair appearing together on the red carpet frequently and Jen continuing to talk about her love for Justin. It appeared to fans that she had finally found the love of her life and that it would really last this time.

Jen and Justin finally headed down the aisle three years later in 2015. In the surprise ceremony, they invited friends (Courtney Cox, Lisa Kudrow, Jason Bateman, Jimmy Kimmel, Ellen DeGeneres, and others) to their Bel-Air home under the impression they were there to celebrate Justin’s birthday, but instead the pair tied the knot!

It all seemed to be a fairytale ending for Jen. But sadly, after just a couple of years together, Jen and Justin decided to split. While the two deeply value their privacy, reports have led to the belief that it was simply a case of “irreconcilable differences”.

After Jen and Justin had their surprise wedding ceremony, they continued with their unorthodox theme and invite friends on their honeymoon. It’s highly unlikely many other couples would have decided to do the same but for this Hollywood couple, it was their first choice.

They had considered having a traditional honeymoon with just the two of them but decided inviting friends would be more fun! Jen and Justin’s group honeymoon consisted of Courtney Cox, Jason Bateman, Chelsea Handler, and others who joined them at The Four Seasons in Bora Bora. Can’t say being the third wheel is too bad.

For the most part, Jen has had the unique ability to remain friends or at least congenial with many of her exes. With Justin Theroux, it was no different. After announcing the ending of their marriage in 2018, the two reportedly still call each other, text, and facetime occasionally.

They have said that they still have a very good, warm friendship but are better off outside of a romantic relationship. Jen even invited him to her Thanksgiving after the split, so it's safe to say that this is one if not the most congenial of her relationships with an ex.

It appears that Theroux hasn’t moved on just yet. In an interview with Esquire magazine, he admitted that, when it comes to dating, he's pretty old-fashioned. He also confessed that dating isn’t really a priority for him right now and that, the “one pivotal relationship in” his life is his mother.

When questioned about his friendship with Jen, he said that “if you love the person the same way you loved them in the relationship, it would behoove you to love them the same way out of the relationship.” We can see why Jen fell for this guy.

Divorce is, of course, one of the most painful and difficult things anyone can go through. Some are very open about the experience, others are very private, even ashamed or embarrassed. But Jen, who has lived most of her life in the spotlight, was refreshingly honest about what she thought about having two divorces in her past.

In fact, she even said she considered them successful and that “when they came to an end, it was a choice that was made” because they “chose to be happy”. And in Jen’s opinion “sometimes happiness didn’t exist” within marriage anymore.

As soon as she was married to Brad Pitt the topic of children was frequently on the magazine covers about when the pair would grow their family. They even went so far as to say it was ultimately the reason for their divorce.

And, in many of her serious relationships after, the public’s questions kept following her. Jen has candidly offered that “some people are just built to...have babies” and that she didn’t know how naturally that comes to her. One thing’s for sure is that Jen won’t let societal standards dictate her life.

Similar to her ex, Justin Theroux, Jen also prefers to get to know someone the old-fashioned way. Part of her relentlessly open mind and heart to finding lasting love does not include dating apps. “Having someone ask you out. That’s the way I would prefer it.” the actress confessed.

After two divorces, she’s not necessarily open to getting married right away. Instead, she’s more about keeping her love life goals simple. She hopes to find “a fantastic partner” with whom she can “live an enjoyable life” and “have fun”. Sounds like she knows what she wants.

Numerous fans of Jen and “Friends” had hoped that her co-star and on-screen romance, David Schwimmer, would become a real-life couple. After watching the actors play two quirky but made-for-each other lovers for so long, it was difficult to think the two couldn’t work in reality.

However, from all outside appearances, it looked like Jen and David were just co-stars and, at best, just friends. Their paths seemed to grow apart after the show ended in 2004, each pursuing relationships and building their careers. Still, some couldn’t help but think that maybe, just maybe, the two could be together someday.

During the “Friends” reunion, the beloved cast got together to reminisce about their favorite moments from the show, both on and off-screen. To the shock (and delight) of fans, both Jen and David Schwimmer admitted that they had a crush on the other during the show.

They further confessed that they could never pursue it because they were in relationships at the time so they channel their feelings for each other into their characters. With both Jen and David single at the time of the reunion, fans waited with anticipation “will it finally happen?!”

Just a few months after the reunion, reports surfaced that Jen and David had been spending more time together and were even dating! Had fans' dreams finally come true? According to the tabloids, they reconnected (especially after the reunion) and were visiting each other, having dinner together, and were spotted looking like potentially more than just friends.

However, a rep denied that the two were a couple. But fans can still dream that after getting along so well together for years on the cast of “Friends” maybe life can finally imitate art.

With her marriage to Justin Theroux over, some may ask who will be the next man to step into her life. While she is a private person, it appears that she is taking the healthy route and focusing her attention on other spheres of life.

Her role in the drama “The Morning Show” has shown a new side of the actress’s capabilities. She has also been involved with brands like “Aveeno,” “SmartWater,” and “Vital Proteins”. With man by her side or not, Jennifer Aniston is determined to live her best life.