Jennifer Aniston has long been one of the most successful starlets in Hollywood, earning wealth, fame, and a legion of adoring fans. But her reign at the top of the industry has also brought with it a great amount of scrutiny and speculation – particularly when it comes to her rather complicated love life. 

While enjoying huge success on-screen, behind-the-scenes, the 55-year-old actress’s personal life has been, in many ways, even more dramatic than the wild storylines she has played out in front of the cameras.

It’s a topic that the actress has struggled to shrug off – and one that has again been brought to the forefront of the public eye after she was seen sporting a large diamond ring on that oh-so-important finger during a series of recent red carpet appearances.

The actress was spotted wearing a mysterious diamond jewelry piece on her left ring finger at both the SAG Awards and the People’s Choice Awards this week, sparking rumors that she may be gearing up to walk down the aisle once again.

Having been through multiple failed marriages, a so-called love triangle, and a bitter battle to conceive children, news of an engagement would no doubt come as a joyous surprise to her fans, as well as her friends.

Over the years, the Hollywood starlet has been linked to many famous faces – including Brad Pitt, Vince Vaughn, John Mayer, and Justin Theroux – but each of her star-studded romances have had the same tragic ending.

Most notable was her relationship with Brad. The two stars, both at the height of their careers, instantly became Hollywood’s new ‘it’ couple when they got together in 1998.

It seemed like a fairytale when they tied the knot in 2000, and by 2004, they were already talking about starting a family together.

But just a year later, what everyone thought would be Jennifer’s long-awaited happy ending turned into a nightmare after rumors erupted that Brad had cheated on her with his Mr. And Mrs. Smith costar Angelina Jolie.

The entire nation became completely engulfed in watching the drama play out, and even decades on, the tale is one that’s known well.

For those who don’t know it, Jennifer and Brad broke up soon after; he and Angelina went on to tie the knot and were together for 11 years before their relationship came to its own explosive end; and Brangelina’s split has now been hailed by some as the messiest breakup in Hollywood history.

While Jennifer was left ‘angry, hurt, and embarrassed’ by the events, she did not give up on her search for her soulmate, and she tied the knot for a second time to Justin years later. But that too ended in another highly-publicized breakup in 2018.

After her second divorce, Jennifer admitted that she’d be taking a break from dating because she needed time to ‘be her own woman’ after being in back-to-back romances since age 20.

She announced that she was finally ‘ready’ to start looking for a partner again in 2021 – but since then, she hasn’t been publicly linked to anyone and has been pretty honest about how ‘difficult’ it’s been for her to be alone.

The actress has also been extremely open about her struggle to conceive, revealing in 2022 – after years of pregnancy rumors and speculation about why she never had a baby – that she tried using IVF to become a mom, but that now, the ‘ship had sailed.’

It certainly hasn’t been an easy road for Jennifer – but does the enormous rock spotted on her finger at the recent award shows mean that she’s finally found love again?

Only time will tell, and as we wait for confirmation, FEMAIL recapped all of her past relationships and heartbreaks from start to finish.

From her and Brad’s messy divorce and the truth about those cheating rumors to her other tumultuous romances, here’s a look into back at Jennifer’s devastating love life.

Her early romances: While Jennifer was rising to the top of the industry, she was involved in a slew of whirlwind romances with some fellow famous faces

In the early years of her career, Jennifer was involved in a slew of whirlwind romances with some fellow famous faces.

While starring in the 1990 TV show Ferris Bueller, she reportedly had a ‘torrid’ affair with her co-star Charlie Schlatter.

GQ editor-in-chief Jim Nelson, who worked as an assistant on the series, lifted a lid on their sultry romance years later.

In the series, which was based on the 1986 John Hughes film, Charlie starred as main character Ferris, while Jennifer portrayed his older sister, Jeannie Bueller.

‘Everyone on set thought she was hot, including Charlie, with whom she had a brief, torrid romance – while playing, it must be said, his older sister,’ Jim wrote in a 2014 GQ article.

‘To we immaturions on the show, this seemed extra-hot. Like performative incest.’

After that came to an end, she was linked to Broadway star Daniel McDonald from 1990 until 1995.

Long after their split, Jennifer described Daniel – who passed away from brain cancer in 2007 – as her ‘first love’ and even admitted that he might have been ‘the one’ for her.

‘He was my first love – five years we were together,’ she told the New York Times in 2015. ‘He would have been the one. But I was 25, and I was stupid.’

Jennifer also had a very brief romance with Counting Crows singer Adam Duritz in 1995, after they reportedly crossed paths at Johnny Depp’s scandal-ridden nightclub, The Viper Room.

Adam later reflected on the short-lived relationship, and he explained that he had ‘no idea who she was’ when they first met.

‘A bunch of my friends lied to me and told me she had a crush on me,’ he explained. ‘And those same friends lied to her and told her I had a crush on her. But I honestly had no idea who she was.

‘She was nice, really funny, really pretty. Those are pretty good requirements for me and also she liked me. It didn’t last very long, but she’s a nice girl.’

After that, Jennifer struck up a romance with actor Tate Donovan, who she dated for three years before they split in 1998.

While they were in the midst of going through their breakup, Tate landed a guest role on Friends as Jennifer’s love interest Joshua – something he later admitted was not easy for them.

‘I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time,’ he recalled of joining the show to Us Weekly.

‘That was tricky, to act like we are just meeting each other and falling in love, [to act] interested in each other, when we were sort of breaking up. That was just tough.’

He added that the reason he was only in the show for six episodes was because it was too ‘painful’ for them to continue filming together.

‘We were like, “Hey, can we not keep doing this? ‘Cause this is really painful and tough,”‘ he continued.

‘It sort of proved that, hey, I guess I’m a pro. If you can go through a tough breakup, and still do your job, then you’re a pro.

‘It was good. It was really ultimately a great experience of how people can treat you really well, and you still do your job even though you’re sort of dying inside.’

The explosive love triangle that captured the nation: She married Brat in 2000, but when they divorced in 2005, rumors erupted that he had cheated on her with his Mr. and Mrs. Smith costar Angelina

What came next was arguably Jennifer’s most publicized romance – her rollercoaster ride marriage to Brad, which ultimately ended in an explosive love triangle that completely captured the nation.

The two stars first met in 1994, but they didn’t start dating until four years later, in 1998, after their managers set them up on a date.

‘That was a really easy evening. It was really fun,’ Jennifer later recalled of their first night together.

The pair officially became boyfriend and girlfriend soon after, and they made their red carpet debut as a couple at the 1999 Emmy Awards.

With both of them at the height of their careers, the public was immediately enthralled with the pairing, and they quickly became Hollywood’s ‘it’ couple.

By November of that year, they confirmed that they were engaged, and they walked down the aisle together in July 2000 on the beach in Malibu, California.

‘We have something special, especially in all this chaos,’ gushed Jennifer of Brad in a 2003 interview.

‘In this nutty, brilliant, wonderful, hard business that we have, it’s nice to have somebody who’s anchored and knows you, really knows all of you.’

And by February 2004, the Friends star confirmed that she and the actor were thinking about starting a family together.

‘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,’ she told The Guardian.

But trouble began brewing in 2005, after Brad grew close to his costar Angelina on set of the flick Mr. and Mrs. Smith.

Almost immediately after the movie wrapped filming later that year, Brad and Jennifer announced that they were separating after five years of marriage.

And when news hit the web that Brad and Angelina were dating just months later, it sparked a slew of rumors that the actor had cheated on Jennifer with his fellow Mr. and Mrs. Smith star.

At the time, Brad and Jennifer shut down accusations that they were going their separate ways due to infidelity through a joint statement that read, ‘Our separation is not the result of any of the speculation reported by the tabloid media.’

Brad also furiously denied that he left Jennifer for Angelina, insisting that his feelings for her ‘came after’ he and his ex-wife split up.

Angelina later confirmed, however, that she and Brad did indeed fall for one another while making the spy thriller.

In an interview with the New York Times in 2008, she described Mr. and Mrs. Smith as ‘the movie where their parents fell in love’ when asked if her kids had seen it.

She also reflected on how their relationship started to Vogue in 2006, explaining, ‘I think we found this strange friendship and partnership that kind of just suddenly happened.

‘I think a few months in [to filming] I realized, “God, I can’t wait to get to work.” Anything we had to do with each other, we just found a lot of joy in it together and a lot of real teamwork. We just became kind of a pair.’

She insisted that ‘it took until the end of the movie shoot’ for them to ‘realize’ that they had feelings for one another and that it ‘a lot of serious consideration’ went into their decision to start dating.

‘It took until, really, the end of the shoot for us, I think, to realize that it might mean something more than we’d earlier allowed ourselves to believe,’ she continued.

‘And both knowing that the reality of that was a big thing, something that was going to take a lot of serious consideration.

‘We spent a lot of time contemplating and thinking and talking about what we both wanted in life and realized that we wanted very, very similar things.’

Jennifer detailed the pain that she felt over Brad getting with Angelina so quickly after their split to Vanity Fair around the same time, and she admitted, ‘I would be a robot if I said I didn’t feel moments of anger, hurt, of embarrassment.

‘I just don’t know what happened. There’s a lot I don’t understand, a lot I don’t know, and probably never will know, really.’

Moving on: Following her messy split from Brad, Jennifer was linked Vince, who she described as her ‘defibrillator’ who ‘brought her back to life,’ and John, who dumped her over their age gap

Following her messy split from Brad, Jennifer quickly entered into a relationship with her The Break-Up costar Vince.

She later described the actor as her ‘defibrillator,’ explaining that he helped ‘bring her back to life’ after she endured the massive heartbreak.

‘I call Vince my defibrillator. He literally brought me back to life,’ she told Vogue in 2008.

‘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. But it sort of ran its course.’

They were together for just about a year before splitting in late 2006.

After meeting at an Oscars party in early 2008, Jennifer then started dating John – but by August of that year, the musician revealed that they had split.

‘There’s no lying, there’s no cheating,’ he insisted of the breakup. ‘People are different, people have different chemistry.

‘I ended a relationship to be alone, because I don’t want to waste somebody’s time if something’s not right.’

They reconciled in February 2009, but went their separate ways again soon after.

John later told Playboy that the reason their romance didn’t work was because Jennifer, who is eight years his senior, was too old for him.

‘Have you ever loved somebody, loved her completely, but had to end the relationship for life reasons? I’ll always be sorry that it didn’t last,’ he said.

‘In some ways I wish I could be with her. But I can’t change the fact that I need to be 32 [years old].

‘One of the most significant differences between us was that I was tweeting … that was a big difference.

‘The brunt of her success came before TMZ and Twitter. I think she’s still hoping it goes back to 1998. She saw my involvement in technology as courting distraction.’

Her second failed marriage: Jennifer wed Justin in 2015, but their romance also ended in divorce three years later, when they decided they were better off as ‘friends’

Back in 2007, Jennifer met Justin while visiting the set of her close pal Adam Sandler’s movie Tropic Thunder, but it wasn’t until they reconnected three years later when they were both cast in the flick Wanderlust that they really grew close.

At the time, Justin was in a relationship with stylist Heidi Bivens – who he had been with for 14 years – and Jennifer has been adamant that nothing romantic happened between them while they were filming the movie.

‘Nothing happened on that movie … We were just friends, great friends,’ she told Good Morning America in 2012.

He quietly split from Heidi in early 2011, and by June of that year, he and Jennifer confirmed they were an item when they were spotted holding hands.

‘I’m very happy. I’m extremely lucky, and I’m extremely happy,’ she said of her new romance at the time.

Justin popped the question in August 2012, and they tied the knot three years later in the backyard of their shared home in Bel Air, California.

In 2016, the actress addressed rumors that she and Justin were expecting their first child together, while slamming ‘the warped way we calculate a woman’s worth’ to The Huffington Post.

‘We don’t need to be married or mothers to be complete,’ she added. “We get to determine our own “happily ever after” for ourselves.’

In an interview with The Sunday Times weeks later, Justin praised his ‘bada**’ wife for the way she handled the constant media speculation.

‘She has lived through a lot of bulls**t. Many people would have crumbled under some of the stresses that have been put on her,’ he said.

‘I’m very proud of her for that, for the way she handles herself. So in a weird way, it’s an honor to stand behind her. Truly, in that sense, she’s amazing.’

In February 2018, however, the couple announced that they were getting a divorce after less than three years of marriage.

‘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.’

Afterwards, Justin insisted that there was ‘no animosity’ between them, and described their split as ‘heartbreaking’ but ‘amicable.’

‘I would say we’ve remained friends,’ he also told Esquire in May 2021. ‘We don’t talk every day, but we call each other. We FaceTime. We text.’

The exes were spotted grabbing dinner together in April 2023, so it seems as though they’re on good terms.

After her split from Justin, Jennifer needed time to ‘be her own woman’ – but announced in 2021 that she was ‘ready’ to date again, and has been open about her ‘difficult’ quest to find love since then

Since her split from Justin, Jennifer has not been linked to anyone publicly – but she hasn’t stopped looking for the one.

Back in September 2021, she discussed her hunt for love with People, and she explained that she was hoping to find someone who was not ‘in the industry’ following her numerous extremely-publicized romances.

She also opened up about her love life during an appearance on the Lunch with Bruce podcast around that same time.

She revealed, ‘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.

‘I didn’t want to for a long time, and I loved really being my own woman without being a part of a couple.

‘I’ve been a part of a couple since I was 20 so there was something really nice about taking the time.’

While chatting with Allure in November 2022, Jennifer admitted that being alone was starting to get to her.

‘There are moments I want to just crawl up in a ball and say, “I need support,”‘ she said.

‘It would be wonderful to come home and fall into somebody’s arms and say, “That was a tough day.”‘

The actress explained that while she longed to have someone by her side, she wasn’t ‘interested’ in walking down the aisle again, but added, ‘Never say never.’

But a source told Us Weekly that Jennifer hadn’t given up, stating, ‘In her gut, Jen believes she’ll eventually meet the right person.’

Jennifer also theorized to WSJ. Magazine in 2023 that her ‘difficult’ childhood had contributed to her not wanting to say ‘I do’ again.

‘I don’t know. My parents… watching my family’s relationship, it didn’t make me kind of go, “Oh, I can’t wait to do that,”‘ she said.

Her father John Aniston, who sadly passed away in November 2022, had married her mom, Nancy Dow, in 1965 – but the couple’s relationship ended in divorce in 1980, when Jennifer was just nine years old.

While reflecting on her long road to finding her soulmate in September 2023, she explained ‘I didn’t like the idea of sacrificing who you were or what you needed, I didn’t really know how to do that. So it was almost easier to just be kind of solo [for the last few years].

‘I’m really good at every other job I have, but [dating is] sort of the one area that’s a little bit difficult [for me].’

Her bitter battle to conceive: Jennifer spoke about her struggle to become a mom while slamming rumors that her past romances ended because she ‘wouldn’t give them a kid’

On top of her difficult hunt to find the one, Jennifer has also been open about her struggle to conceive.

She spoke about her bitter battle to become a mom with Allure in November 2022, while slamming rumors that her former relationships had ended because she ‘wouldn’t give’ her exes ‘a kid.’

‘I was trying to get pregnant. It was a challenging road for me – the baby-making road,’ she told the publication.

‘All the years and years and years of speculation… It was really hard. I was going through IVF, drinking Chinese teas, you name it. I was throwing everything at it.

‘[But] the reason my husband left me, why we broke up and ended our marriage, was because I wouldn’t give him a kid – that was absolute lies. I don’t have anything to hide at this point.’

She also spoke about the regret she felt over not ‘freezing her eggs’ when she was younger, adding, ‘I would’ve given anything if someone had said to me, “Freeze your eggs. Do yourself a favor.” You just don’t think it. So here I am today. The ship has sailed.’

Jennifer admitted that she was too focused on her career to think about the fact that her future self may one day want to settle down and have children, and hit out at the constant scrutiny she faced for not getting pregnant during her five-year marriage to Brad.

‘I just cared about my career. And God forbid a woman is successful and doesn’t have a child,’ she said.

She described the glaring spotlight of scrutiny she faced during this time – with people constantly questioning whether she was showing off a baby bump in paparazzi photos – as ‘frustrating’ and ‘maddening,’ adding that she isn’t a ‘superhuman’ who could stand that kind of commentary without feeling some level of ‘hurt.’

The actress insisted, however, that she had now come to terms with the fact that she won’t have children, noting that she actually feels some ‘relief’ in the fact that the possibility of kids is no longer lingering over her as never-ending ‘maybe.’

While this was the first time she spoke in detail about her IVF struggles, Jennifer previously opened up about some the ‘pressure’ she felt to have a baby.

‘I don’t think it’s fair. You may not have a child come out of your vagina, but that doesn’t mean you aren’t mothering – dogs, friends, friends’ children,’ she said in 2014.

‘This continually is said about me: that I was so career-driven and focused on myself that I don’t want to be a mother, and how selfish that is. Even saying it gets me a little tight in my throat .’

She also stated in a separate interview, ‘I don’t have this sort of checklist of things that have to be done and if they’re not checked, then I’ve failed some part of my feminism or my being a woman or my worth and my value as a woman because I haven’t birthed a child.

‘I’ve birthed a lot of things, and I feel like I’ve mothered many things. And I don’t feel like it’s fair to put that pressure on people.

‘I just find it to be energy that is unnecessary and not really fair for those who may or may not [have children].

‘Who knows what the reason is, why people aren’t having kids. There’s a lot of reasons that could be, and maybe it’s something that no one wants to discuss.’