What We Know About Madonna's Relationship With Josh Popper

In addition to Madonna's countless hit records such as "Material Girl" and "Vogue," her dating history has equally intrigued fans. Madonna has dated some of entertainment's biggest names over the years, including Sean Penn, Michael Jackson, and even Tupac Shakur.  In the years since her most high-profile romances, the singer has been in the news for her connections to several younger men. In 2018, she famously began dating her backup dancer, Ahlamalik Williams, who was just 28 when they split in 2022. In September that year, Madonna started seeing 23-year-old model Andrew Darnell, though the union fizzled after just five months. 

The string of young men comes as no surprise, with a close friend telling Page Six, "She likes the idea of a guy being younger than her daughter. It announces her desirability to the world." Therefore, it came as no surprise when Madonna snagged 30-year-old athlete Josh Popper. The two have been together since at least February 2023 and seem to be still going strong. And while he may be making headlines as the singer's boyfriend, Popper is carving out an impressive life for himself in the sports world.

For years, Josh Popper was an inspiring pro football player. He attended Rowan University in Glassboro, New Jersey, where he played defensive lineman on the school's football team. One of Popper's most significant college career highlights was assisting his team in their New Jersey Athletic Conference Championship win in 2013. He also appeared with his fellow players in two NCAA games in 2012 and 2013. This attracted the Arizona Cardinals, who asked Popper to attend its rookie minicamp in May 2016. After being cut before the season began, Popper trained with the Indianapolis Colts the following year. Unfortunately, he was also released by them before making his professional debut.

After his football dreams faded, Popper turned his attention to boxing. He began training in anticipation for his own career, sharing videos on Instagram as early as 2019 of him working out in the ring. His interests led him to open Bredwinners Boxing Studio in 2021 in New York. It was here that Popper met Madonna while training her son David Banda. Popper and fellow trainer Coach Ruben help aspiring men and women who wish to compete or use boxing as a means of shedding pounds. Per the gym's website, "Regardless of your experience in the sport, our top-notch trainers will teach you to box the right way, incorporating fundamental footwork and punches alongside a great workout." Popper also competes in matches, securing his most recent win in October 2023.

Josh Popper may look familiar to some, as he once appeared on the Bravo series "Summer House." During the second episode of Season 7, Samantha Feher frequented Popper's Bredwinner Boxing Studio. She felt an attraction to the coach and invited him to hang out with her at the Hamptons share house. However, once there, they didn't hit it off as planned, though they remained friends. In fact, she has even spoken to him about his romance with Madonna, but he wouldn't exactly confirm nor deny it. Feher told Page Six in April 2023, "We messaged about it jokingly of like, 'Oh, if this is true, that's baller,' and he's very vague. No one knows the truth."

 In April 2023, Popper sat at a dinner table with Madonna and her kiddos in an Instagram skit ahead of a concert in Mexico. In August 2023, the singer supported Popper at a boxing match in New York, holding his championship belt in a photograph alongside him. That same month, Popper took some time off to accompany the family on vacation to Lisbon before appearing in a stage video for Madonna's October 2023 concert in New York. While the couple has not conducted interviews about one another, it's clear they're enjoying a lot of time together.