John Mayer and Aniston, pictured here in 2009, dated on and off for about a year. Though his "Shadow Days" are over now, in 2010 Mayer opened up to Rolling Stone about his split with Aniston, saying, "I've never really gotten over it. It was one of the worst times of my life."
Real-life couple Vince Vaughn and Aniston co-starred in 2006's "The Break-Up," which is coincidentally what the couple did later that year.
Aniston dated British model Paul Sculfor in 2007, according to People.
Brad Pitt and Aniston, shown here at the premiere of "The Mexican" in 2001, began dating in 1998. The pair married in 2000 and announced their separation in 2005, the same year Pitt and Angelina Jolie's "Mr. and Mrs. Smith" hit theaters.
Tate Donovan and Aniston were engaged in the mid-'90s. Before the couple called it quits, he appeared on "Friends" as the boyfriend of Aniston's character, Rachel Greene.
Counting Crows frontman Adam Duritz and Aniston dated in 1995. "We never even slept together," Duritz once said of their romance, via US Weekly.
Aniston and Charlie Schlatter appeared side by side on NBC's "Ferris Bueller" series in1990. The sitcom was short-lived, as was the couple's relationship.