4. Kristen Stewart – Michael Angarano
Kristen Stewart may be best known for her role in the Twilight films and being the long term squeeze of Robert Pattinson. Prior to breaking Pattinson’s heart, Stewart was dating actor Michael Angarano back in 2005 after they met during the filming of the indie drama Speak. At the time, Stewart was 15 and Angarano 17. The moody female star dated him for four years and allegedly lost her virginity to him. But then she met Robert Pattinson and her relationship with Angarano was subsequently ended.
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