Jennifer Aniston is an actress who has lived a very fulfilling life with an even more fulfilling career as a respected member of her field. She has made a ton of money, she has landed some big roles, she has found huge success in both the tv and movie worlds, and every now and again, she pulled off a truly great acting performance that receives cheers from her peers. Can't get much better than that.
Except for maybe the respect of the fans and the media, who for whatever reason, tend to obsess far more over Jennifer Aniston's love life than her actual career. Then again, to their credit, she has a rather interesting (if not, perplexing and occasionally bizarre) romantic history. Whether we are talking about her boyfriends or her husbands, so many head-scratching, fascinating facts came out of each of her relationships - some that even her die-hard fans may not know about.
20 Adam Duritz Dated Her *AND* Courteney Cox
One of Jennifer Aniston's earliest famous lovers was Counting Crows lead singer, Adam Duritz. They dated briefly in 1995. On paper especially, this pairing sounds as random as can be, but apparently, Duritz must be a really charming fellow as he later went on to date Aniston's Friends co-star, Courteney Cox.
19 Daniel McDonald Was Her First Love
Another rendezvous that Jennifer Aniston had back in the day was a fling with late fellow actor Daniel McDonald. After he passed away in 2007, Aniston admitted in an interview with Rolling Stone that the Tony-nominated actor was the first love of her life, though they broke up after five years together. After they broke up, she moved to New York and joined the cast of Friends.
18 She and Brad Argued About Smoking
According to Us Weekly, one of Brad Pitt's pet peeves about his now ex-wife was that he smoked. Which is funny, because she, too, is a smoker. Their arguments often focused around each other's smoking habits, but Aniston finally managed to kick her habit back in 2012. Kudos to her.
17 She and Justin Theroux Ate Dinner Unclad
Every couple has their strange rituals that help spice up their love life, but this one might have been flat out bizarre (or at least a little unsanitary). According to OK! Magazine, coming from a source close to Jennifer Aniston, when she was married to Justin Theroux, they often ate dinner in the nude in hopes of being "passionate."
16 Tate Donovan Dated Jen Onscreen As They Were Breaking Up in Real Life
While dating Jennifer Aniston in 1998, Tate Donovan landed a gig on Friends for a six-episode arc dating Aniston's character onscreen. This sounds cool on paper until we learned from a 2018 US Weekly interview that they were breaking up during filming. In the interview, he discussed the difficulties in trying to act with an ex as if they were just falling in love and then, eventually, falling out of love all over again.
15 Met Paul Rudd When He Ran Over Her Foot
Paul Rudd has starred in several films with Jennifer Aniston and they became good friends in real life, but they started off on rocky terms. In an episode of the Graham Norton Show, Rudd explained that he landed a role on Friends in 2002, but upon arriving at the set, he accidentally ran over Aniston's foot. He worried he'd lost his job, but somehow gained a friend out of it.
14 The Paparazzi Forced Jen and Vince Vaughn to Break Up
The go-to joke with these two is that because they starred in The Break-Up, Vince Vaughn and Jennifer Aniston were always destined to "break up." However, as Vaughn explained to Playboy Magazine in 2015, he did not like that dating a huge celeb came with always being bombarded by paparazzi. That played a big factor in the breakup.
13 Ben Stiller Introduced Her To Justin
She sounds like a random game of Six Degrees of Kevin Bacon, but comedian, director, actor, producer, and writer, Ben Stiller was the link that brought Justin Theroux and Jennifer Aniston together. The pair met in 2007 on the set of Stiller's 2008 movie Tropic Thunder, which Justin appeared in. Stiller introduced Aniston directly to Theroux on a day she visited the set.
12 She Dated The Man Who Played Her Brother on Ferris Bueller
Not a lot of people remember this, but NBC ran a tv show adaptation of Ferris Bueller's Day Off. It bombed in the ratings and lasted only a season, but it was one of Aniston's first cable tv gigs. She played Ferris's sister and, coincidentally offset, fell in love with the guy playing Ferris, Charlie Schlatter.
11 She and Brad Are Still Rumored to Get Back Together
In 2018, an unnamed source told Us Weekly that Jennifer Aniston had no intention of even "consider being with Brad in a romantic way” again. However, rumors persist that they are getting back together, as recently as this week amid reports that Pitt surprised Aniston with flowers at the People's Choice Awards backstage (which Gossip Cop confirmed did not happen).
10 Sources Say She Broke Up with John Mayer Over Twitter Obsession
John Mayer and Jennifer Aniston had a relationship that lasted almost a year between April 2008 and March 2009. The reason they broke up, according to a source that spoke to The Telegraph, it was all because of Aniston got sick of what she deemed to be a "Twitter obsession" from her younger man.
9 Mayer Implied He Broke Up With Her Because She Was Too Old
John Mayer himself has a different side of the story to their break up. After they broke up, Mayer did an interview with Playboy Magazine where he admitted, "In some ways, I wish I could be with her. But I can’t change the fact that I need to be 32." The quote seems to imply that their relationship would've worked if he was closer to her age.
8 First Date with Jon Stewart Wasn't Quite a Date
When Jennifer Aniston served as a guest on The Daily Show, Jon Stewart recalled how the two went on a date together back in the 90's. However, Aniston recalled it much differently, bursting his bubble. She recalled it as her hanging out with a bunch of friends for dinner, and her then asking the future talk show host to tag along. Doesn't sound like a date at all.
7 Justin and Jen Helped Pick An Engagement Ring for Jason Sudeikis
Just because they starred in We're the Millers together, Jason Sudeikis was rumored to be dating Jennifer Aniston. Obviously, she was already dating Justin Theroux at the time and Sudeikis with Olivia Wilde at the time, so that was not true. However, Jen told E! News that her and Justin were friendly enough to help him pick out his engagement ring for Wilde when he was ready to marry her.
6 Owen Wilson Woo'd Her By Being Funny
As with the case with most actors who work together (or, let's face it, any actor who works on set with Jennifer Aniston), rumors sparked that Owen Wilson started dating Jennifer Aniston after they filmed Marley and Me together. According to some reports, Wilson charmed Aniston just by being a funny guy.
5 She Dates Normal, Creative Tech Guys, Too
Jennifer Aniston has always been closely linked to famous celebrities as her suitors, but let us not act like she does not partake in a bowl of normie soup from time to time. As reported by US Weekly back in July, Aniston was pursuing a pretty normal "tech" guy at the time. He was not named, but apparently, he may be a mogul.
4 Katy Perry Warned Her to Stay Away from Orlando Bloom
Earlier this summer, Life & Style Magazine reported that Jennifer Aniston had sent some questionable, inappropriate, and overall flirty texts with pictures to Orlando Bloom's phone. Jen might not have known that Bloom is spoken for by Katy Perry, who the magazine's source says wished Jen would just "back off."
3 Bradley Cooper Has Dated Jen *AND* Angelina Jolie
More recently, the tabloids have continued to claim that Bradley Cooper is now dating Angelina Jolie, although Gossip Cop has debunked rumors of this ilk. But if these rumors are true, that would mean he's dated both Jolie AND Jennifer Aniston. Which, given how they both share another former flame, that is... interesting to say the least.
2 Gerard Butler Thinks She's a Better Kisser Than Angie Jolie
During a 2008 guest appearance on Watch What Happens Live With Andy Cohen, Gerard Butler was asked which of his former co-stars were better kissers: Jennifer Aniston or Angelina Jolie. The Scottish actor and title star of The Phantom of the Opera went with his ex, Aniston. Smart call, mate.
1 She's Still Friends with Her Exes
It takes a special kindhearted and forgiven soul to remain friends with an ex, and from the looks of it, Jennifer Aniston is that kind of soul. Even with her ex-husband, Justin Theroux, as they follow each other on social media and comment on each other's posts. Plus, Theroux, Brad Pitt, and John Mayer were all invited and attended Jennifer Aniston's 50th birthday party this year, according to People Magazine.
Sources: people.com, gossipcop.com, Instagram