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At 65, Madonna reportedly split up with her 30-year-old boyfriend, Josh Popper.
As The US Sun reported, the pop icon has struggled with her relationship with Popper, 35 years her junior, after spending seven grueling months at the Celebration Tour.
Madonna then told her close pals that she was single again after breaking up with the boxing trainer.
"Madonna has barely seen Josh for months because her schedule was so hectic. Things just fizzled out," the insider alleged. "There is genuinely no bad blood - they're still fond of each other. At the moment their relationship doesn't feel feasible and they've cooled things off, but they are staying friends."
Unbeknownst to many, Popper was beside Madonna when she was hospitalized because of a bacterial infection that put her into comatose. Popper was also in attendance when Madonna's family flew to Portugal last August 2023 for her birthday.
It was there when Popper got the approval of Madonna's eldest son, Rocco Ritchie.
Madonna and Popper were introduced to each other after the latter began giving her son, David Banda, some boxing lessons.
READ ALSO : Madonna Makes History as The First Female Singer to Complete 6 Tours Exceeding $100 Million Each
Meanwhile, Page Six reported that the two were last seen together in March 2024 when Madonna was spotted watching her ex-beau's match in New York City. However, the outlet's sources shared information about Madonna's current state after the breakup.
"Madonna doesn't date losers," the source said. "She looked good."
As for Popper, his last post about Madonna on Instagram was on Valentine's Day. He shared photos of them on their trip to Portugal and expressed how he missed the place.
In 2019, Madonna spoke about having unconventional relationships and how people perceived them in an interview with The Sun.
"I refuse to bend a knee to convention and what society expects of me as a woman," she shared. "I was lucky enough to have a life as an artist before the phone and Instagram and social media because I did have that time to develop as an artist and a human without feeling the pressure of judgment of other people or comparing myself to other people."
The "Like A Virgin" singer claimed that Instagram was created to make people feel bad, as they have become "slaves" to "winning people's approvals."
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