Ben Affleck
His stunning overnight success with the Oscar-winning film “Good Will Hunting” ended Ben’s seven-year romance with high school love Cheyenne Rothman in 1997. “Cheyenne remembers the sweet, caring, thoughtful young man who was enthusiastic about the screenplay he was perfecting,” said a source. Now a married mom of three living near Oakland, Calif., “Cheyenne has moved on,” the spy said, but Ben, 46, “retains a great level of respect for her.”
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LEONARDO DiCAPRIO
Serial dater Leo has wooed an endless stream of hot, young models — and not one has been older than 25! Now 44, he’s currently seeing Al Pacino’s stepdaughter, Camila Morrone, who’s 22. Despite all his practice, some grumble Leo’s a dud in bed! “One model complained that he put on headphones and started vaping while they were in bed and gestured to her to carry on while he lay there and zoned out,” dished a source.
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Brad Pitt
When Brad was a University of Missouri student, “ladies would line up to speak to him — as if he was already famous! They didn’t mind that he hated showering and smelled bad,” squealed an old college pal. But Brad was “madly in love” with Josie Rosen! “She wasn’t the jealous type and they had an incredibly strong bond,” said the pal. Josie, now 55, moved to L.A. in the late ’80s and is a successful producer.
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George Clooney
Before he hit it big, George dated then- 22-year-old Kathy Penno in Cincinnati, Ohio, in the early ’80s. “He was younger than me, but he wasn’t a virgin,” she recalled. “He had a basement apartment with just a director’s chair and a mattress on the floor. We broke up because he left for California. The last time I saw him was at a bar in town and he was telling me how excited he was about filming ‘ER.’”
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