Jennifer Aniston fans around the world were heartbroken when she and her husband of two years, Justin Theroux, announced their separation on February 15. Jen looked quite happy in her relationship and her marriage, so this is a shock.
But, the recent revelations that Justin Theroux allegedly had “reservations” about marrying Jennifer Aniston, as well as her friends who thought his personality was perhaps a bit too dark for the upbeat Californian, may have fans scratching their heads that perhaps Jennifer Aniston was going out with the wrong guy.
Looking over her 28 years of of dating, with two failed marriages thrown in, it appears that the talented actress dated more than her fair share of bad boys and commitment-phobes that all wound up breaking her heart, and is why she is single now.
Who has Jen dated over the years, and what do we know about these relationships?
Jennifer’s most recent relationship is her now-estranged husband Justin Theroux. Jennifer met The Leftovers actor in 2007, on the set of the movie Tropic Thunder. But, according to Cosmopolitan.
Jennifer later told PopSugar that she thought he was “the nicest person in the world,” but also gave off “serial killer” vibes. Well he has a collection of human and animal teeth, as well as disfigured people hanging on his New York apartment walls.
Perhaps that was her first sign of trouble?
t was not until 2011 that the couple first dated. In 2012, Jennifer spoke to InStyle, where she explained that after dating a lot of wrong guys, she finally found the right one who suited her.
“Having experienced everything you don’t want in a partner over time, it starts to narrow down to what you actually do want. As I get older I realize what qualities are important in love and what suits me. And what I won’t settle for.”
They were engaged in 2012 and then married in 2015. Just days after the announcement that they are separated, Us Magazine spoke to a source who claims that “constant scrutiny” of her love life made Jennifer “insecure” in her relationships, and only marriage would stop the gossip, and then she would feel more secure.
“It was obvious Jen needed more than an engagement or to be life partners with Justin. He didn’t want to lose her, so they got married.”
Yet, according to a source that spoke to E!, there was a lot of love, but the “free spirit” Theroux is “more nomadic” and Jennifer is not “that kind of person.”
Did they date or didn’t they? According to The Sun, “Jen’s rep” denied Jennifer and the suave Scotsman ever dated, yet there were reports that the two were dining in a New York restaurant and holding hands back in 2010.
The commitment-phobe, serial-dating Phantom of the Opera star has been playing the field since he emerged in Hollywood over 13 years ago.
— InStyle (@InStyle) February 20, 2018
According to Popsugar, the couple dated off and on between 2008-2009. It was clear that serial dater John Mayer was into her, but not into her fame.
The report from a kiss and tell interview that the “Why Georgia Why” singer did with Playboy described Jennifer as the “sweetest, kindest person.”
Then he later explained how if he had continued on with her, it would have been the love he always “wanted.”
“Because if it had worked out, I would have reaped the benefits. I would be sitting here saying, ‘What I have when I go home is the thing I’ve always wanted.'”
“I don’t smoke, and I don’t go out in the sun, and I don’t love anybody." https://t.co/xK5d13x0Ok
— The Cut (@TheCut) February 13, 2018
In 2007, Jennifer briefly dated Brad Pitt look-a-like British model Paul Sculfor. He was a known serial dater, having previously dated Cameron Diaz. According to The Independent, the Britain’s Next Top Model judge is now married to socialite Federica Amati. They had a ceremony that he described as a “dream wedding.”
Jennifer met Vaughn on the set of The Break-Up soon after she parted ways with Brad Pitt. The relationship should have been called “The Rebound,” as it lasted about a year, from 2005-2006.
There were unfounded rumors that Vaughn was “unfaithful.” CNN reported that the Wedding Crashers actor threatened three tabloids who printed stories that he was kissing an unidentified blonde, yet the couple split up not long after that.
Fight Sports: Vince Vaughn Earns Blue Belt In BJJ https://t.co/eIUDz1dzqd
— BJJ News (@bjjnews) February 9, 2018
Set up on a date by their agents and dubbed the “golden couple,” the two actors dated from 1998 until they married in 2000 in what the New York Post describes as a “lavish 1 million Malibu wedding.”
They broke it off in 2005 after a Caribbean vacation with Courteney Cox and her then-husband, David Arquette. After their vacation in the first week of January of that year, the couple released a statement that they decided to separate. There were rumors that he wanted kids and she wanted to build her career. There were also rumors about Brad’s closeness to his Mr. and Mrs. Smith co-star, Angelina Jolie. Those close to Brad insisted that he was a one-woman guy.
The truth eventually came out that there was a Brad and Angelina affair, and perhaps Jennifer even had a feeling about their budding relationship.
People spoke to someone close to Jen, right after the separation, who said that even after six years together, The Good Girl actress was still unsure if the relationship would last.
“She has been resisting having a child for a number of reasons. One was her career. Also, she wanted to make sure that [the marriage] would last. There was a little doubt that crept in.”
Now that Pitt is getting divorced, many want the golden couple to reunite. But, many may have to ask why, in reference to Jen’s extreme heartache over Brad’s ultimate betrayal.
The one where Jennifer Aniston and Brad Pitt are both single in 2018. (Does anyone smell lobster?) https://t.co/Nvk8Vi3wwM
— E! News (@enews) February 16, 2018
Jennifer and Paul dated around the time they filmed the movie The Object Of My Affection, but as a couple, Paul and Jen didn’t work out. Yet, Rudd’s career certainly did, as the Clueless actor wound up as Phoebe’s husband Mike on Friends. He married his publicist Julie Yaeger in 2003 and the couple has two children.
Commitment-phobe actor Tate Donovan was engaged to Sandra Bullock for a few years before he started dating Jennifer Aniston from 1995-1998. The two also actually got engaged, yet The Sun reports that when Donovan appeared on Friends as Joshua, Rachel’s love interest, the two were on the way out and it was pretty horrible.
The Argo actor eventually did get married to Corinne Kingsbury, but that only lasted for a few years.
— CBS Drama (@CBSDrama) December 20, 2017
Jennifer dated the still single Counting Crows singer in 1995. Not much later, her Friends co-star and best pal, Courteney Cox later dated him, as well as Wynona Ryder, who infamously kissed Jennifer when she was played her old sorority sister on a Friends episode.
When Jennifer looked back on her “first love” actor Daniel McDonald, she remembered him with tender memories. The couple dated from 1990-1994. The relationship ended when she started working on Friends. McDonald died in 2007 from brain cancer.
— Elizabeth Reidenbach (@EReidenbach) January 9, 2015
According to the Toronto Sun, who quoted a New York Times article, Jennifer spoke about Daniel, but not by name.
“He would have been the one, but I was 25 and I was stupid.”
She did say, “He must have sent me Justin to make up for it all.”
Perhaps Jennifer is rethinking that statement right now.