Jennifer Aniston is without a doubt one of the biggest celebs in Hollywood, and has been since her 1990's debut! After playing one of the most iconic characters on the hit television sitcom "Friends", Jennifer Aniston was an instant success and a force to be reckoned with.
The star was not only known for her acting, but she was also jaw-droppingly gorgeous! Aniston dated quite a bit throughout the 90s before her first marriage in 2000 to actor Brad Pitt. Despite the marriage failing 5 years later, Jennifer proved herself to be someone that you don't play around with, considering she was back in the dating game and ready to get out there.
Aniston would soon find herself appearing on a number of headlines after jumping into her first relationship after her divorce, but yet again, things didn't work out for her. It appears Rachel has yet to find her Ross, but we have no doubt that her time will come.
10 Charlie Schlatter
Before Jennifer Aniston was the ever so popular Rachel Green on the hit television sitcom "Friends", she appeared alongside Charlie Schlatter on the short-lived 1990 TV adaptation of 'Ferris Bueller's Day Off'. Both Jennifer and Charlie started alongside one another and even had a secret relationship. While the two were rumoured to be together back in the 90s, neither of them ever confirmed that they did, in fact, date. However, flash forward 14 years, and the 1990 show creator came forward claiming the two undoubtedly shared a short but sweet romance, one that most of the people working on the show knew about.
9 Adam Duritz
Jennifer Aniston was now a part of one of the biggest shows to ever air on television! "Friends" was an instant success, and considering Aniston was playing the role of the "it" girl Rachel Green, she was without a doubt a hot commodity. In 1995, the actress began dating musician Adam Duritz, which many people were confused about because of how different the two were. Despite the unlikely pairing, Aniston and Duritz dated for a few months before calling it quits! Duritz himself later moved on with Aniston's co-star and best friend, Courteney Cox, which also didn't end well.
8 Tate Donovan
Tate Donovan and Jennifer Aniston were also a couple once upon a time! Donovan guest-starred on "Friends" back in 1998 and ended up scoring a six-episode arc where he would play Rachel's boyfriend. While many fans of the show believe these two met on the set of "Friends" and later began their relationship, it is the complete opposite! Donovan revealed that he and Aniston had been dating prior to him even scoring a spot on the show, and while he was happy to have landed the gig, it came at the same time that he and Aniston were breaking up. This obviously made the situation harder than anticipated, considering the two had to work alongside one another during their separation.
7 Paul Rudd
We are not sure how Phoebe Buffay is going to react to this one! Prior to Paul Rudd playing the hilarious piano playing lawyer on "Friends" who goes on to marry our beloved Phoebe Buffay, played by Lisa Kudrow, he dated Jennifer Aniston! The two had a brief relationship back in 1998 after working together on "The Newtown Boys". Aniston and Rudd dated after her break up with Tate Donovan and before Rudd would even appear on the sitcom. While their relationship didn't last, they remained friends during their time working together on the Warner Brothers show from 2002 - 2004, and their 2012 film "Wanderlust".
6 Brad Pitt
This is without a doubt a love story everybody wished would have never ended! Jennifer Aniston began dating Hollywood heartthrob Brad Pitt after her split from Paul Rudd. The two began dating seriously in late 1998 and were married by 2000. Brad Pitt would go on to make an appearance on "Friends" during the iconic thanksgiving episode, where fans could not get enough of some on-screen Brad Pitt. Despite the two being one of the best Hollywood couples to date, things took a turn after Pitt worked with Angelina Jolie on their 2005 film "Mr. & Mrs. Smith", which ultimately ended his marriage with Aniston.
5 Vince Vaughn
Considering just how beautiful and successful Jennifer Aniston was, there was no doubt that she would be able to bounce back from her first divorce and fall into the arms of yet another Hollywood actor. Aniston began dating actor Vince Vaughn while the two worked together on the 2006 film "The Break Up", and although they made a pretty decent couple, the two eventually broke up that same year. Vince Vaughn looks back at their time together with nothing but fond memories, claiming that the incessant media coverage and paparazzi were too much for them to handle, causing them to split up.
4 John Mayer
While actors were definitely Jennifer Aniston's type, it appears as if she was ready for some music in her life. The actress began dating singer John Mayer in 2008 and did so on and off up until March of 2009. Although the couple looked great together, it seems as if Mayer was just not the guy for Jennifer! Aniston herself claimed that John Mayer was "just a jerk" while they were dating, which didn't sit well with Aniston, leading them to officially call it quits.
3 Bradley Cooper
It was made clear that the music route was just not it for Jennifer Aniston, so back to basics it was! The sitcom turn rom-com queen Jennifer Aniston began dating Hollywood hunk Bradley Cooper soon after her split from John Mayer. The two spent the summer of 2009 together after having met and worked on "He's Just Not That Into You". Although their romantic relationship, or summer fling some might say, did not last long, it appears as if the two remained close friends, and have been to this very day.
2 Gerard Butler
As if one Hollywood hunk was not enough, Aniston soon moved on to British actor, Gerard Butler. The two worked alongside one another in the film "The Bounty Hunter", which immediately sparked dating rumours between the two. While neither Jennifer or Gerard ever confirmed or denied the rumours, the two would be caught spending quite a lot of time off-set with one another, which made the headlines more believable. Whether it was a publicity stunt for the film, or they genuinely saw something in each other, it's safe to say they made quite a dashing couple.
1 Justin Theroux
Justin Theroux was imagined to be Jennifer Aniston's happily ever after, but alas, he was not. After being introduced by Ben Stiller in 2007, the couple didn't officially begin dating until 2011 after making their relationship public at the MTV Movie Awards. Justin later proposed to Jen in 2012, and the two were married three years later. It appeared to be a match made in heaven, however, come 2018, the couple announced they were officially filing for divorce. Aniston claims the "decision was mutual and lovingly made", however, we can't help but wonder when Jen will find her real-life Ross.