9. Madonna
The pop icon has several relationships under her belt (hey, she’s in her 50s), and if you’ve been following Madonna’s career for years, you know that she went through hell during her marriage to Sean Penn. The divorce proceedings weren’t so pretty either, but the two seem to be the best of friends these days. Guy Ritchie, who was also married to Madonna, put her through hard times during the divorce proceedings as well. The couple called it quits in 2008, and since Madonna is considerably wealthier than Ritchie, she was required to pay spousal support–$76 to $92 million. She was required to pay in order to legally end their marriage, and cited “unreasonable behavior” as the reason for their divorce. No wonder she’s not in a hurry to get married again.
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