Life imitating art? By June 2005, Aniston rebounds with Vaughn, her costar in The Break-Up. The two share affectionate dates in his Chicago hometown and jet-set to her favorite Mexican getaway, fueling reports of an impending wedding. By the end of 2006, the couple break up.
In 2009, the rocker helps Aniston celebrate her big 4-0 with a very special present: a song. Following a year of off-and-on dating, the couple call it quits for good a month after attending the 2009 Academy Awards together – though Mayer later admits he's "never really gotten over it."
The Bounty Hunter costars' flirtation seems to play out when the cameras aren't rolling: They are spotted hand-in-hand (and with the Scottish actor's hand on her backside) as the two promote their film in 2009. "I literally became a member of her family," Butler told PEOPLE of their relationship a year later.
First linked in 2009 when they costarred in He's Just Not That Into You, talk of an Aniston-Cooper romance reignites after the actor's 2011 split from longtime girlfriend Renée Zellweger. "Jen always had a soft spot for Bradley, and she thinks he is very attractive and charming," a source tells PEOPLE, but soon after, Aniston steps out with Justin Theroux.
It was total puppy love for Aniston and her beloved Welsh corgi-terrier mix, who died in 2011 at age 15. "He's my baby boy. Norman goes with me on location – I've got to take Norman," she told PEOPLE of the most enduring, steady relationship in her life. She later debuts an inked commemoration for her furry friend.