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Sylvester Stallone and Jennifer Flavin – $410M
Much like Sylvester Stallone’s tale about his rise to fame, his love story with Jennifer Flavin played out in an interesting way. They met in the late ‘80s and dated until 1994 when Stallone abruptly ended things in a rather hurtful way. He decided to end their relationship through a six-page letter he sent to her via Fed-Ex.
It turned out that Stallone had started seeing Janice Dickson who claimed that he had gotten her pregnant. Eventually, he found out that the child wasn’t his and he worked on his relationship with Flavin. They married in 1997 and the daughter they share was even present to watch them exchange their vows.
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