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Jennifer Aniston and Gerard Butler, 2009
Charlie Schlatter and Jennifer Aniston, 1990
Jennifer Aniston and Adam Duritz, 1995
Jennifer Aniston and Tate Donovan on "Friends"
Brad Pitt and Jennifer Aniston, 2004
Vince Vaughn and Jennifer Aniston in "The Break-Up"
Paul Sculfor, circa 2007
John Mayer and Jennifer Aniston, 2009
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The Many Men of Jen | 2 of 10
Charlie Schlatter and Jennifer Aniston, 1990
Think you can do better? Respond with your own gallery now!The Many Men of Jen
Charlie Schlatter and Jennifer Aniston, 1988-1989
Charlie Schlatter was an emerging movie star ("Bright Lights, Big City" and "18 Again!") when he and Jennifer Aniston met on the set of the TV series "Ferris Bueller" (a small-screen remake of the Matthew Broderick-Jennifer Grey film). "Bueller" was Aniston's first big break (after a short-lived sitcom and a TV movie), and she was just 21. Jen and Charlie only lasted about a year (outliving "Bueller's" 13-episode run), but this pairing proved young love usually doesn't last.
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