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.
Josh Hopkins — Maybe?
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.
Justin Theroux — The Beginning
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.
Justin Theroux — The Relationship Blossoms
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.