Madonna Has An Interesting History With Summer House's Andrea Denver

Madonna may be a pop icon, but her fascinating love life has also kept people talking over the decades. From Madonna's first marriage to Sean Penn, her second marriage to Guy Ritchie, or her secret romance with rapper Tupac (per In Style) that she managed to tuck between her nuptials, she truly has a "Rebel Heart." In 2022, Madonna revealed on her Youtube channel that she regretted both marriages, but she hasn't given up on love altogether.  

Since Madonna divorced Ritchie in 2008, she's been attached to several other suitors, including several younger men. By the way, she's well aware of the public's reaction to the large gaps in age between her and her partners. "I have lovers who are three decades younger than me," shared Madonna with Harper's Bazaar. "This makes people very uncomfortable. I feel like everything I do makes people feel really uncomfortable." Recently, the "Material Girl" singer linked to Ahlamalik Williams — her backup dancer, who's 35 years her junior, per Page Six. And while Madonna's romance with Williams may be over now, she once had an interesting relationship with another younger suitor: "Summer House" alum, Andrea Denver.

In 2015, Madonna sparked the internet's curiosity when she posted a shirtless photo of Andrea Denver to Instagram. According to TMZ, Madonna snatched the professional shot from Denver's Instagram account, and captioned it, "Rebel 8 pac!! Hell to the Yeah!" At the time, Denver was working solely as a model, who'd appeared in Taylor Swift's "Blank Space" music video and an episode of "Family Feud," per IMDb, as "Summer House" hadn't yet premiered. According to the outlet, Denver was flattered by Madonna's appreciation, and allegedly remarked, "I'd definitely go on a date with her."

And while there's no way to know for sure if Denver actually expressed romantic interest at the time, Denver did repost Madonna's post to his Instagram. "Thank you @madonna! You are such an icon!" wrote Denver. As the Daily Mail points out, Madonna's post came just a few weeks after she broke up with Timor Steffens, a relationship which sources close to the couple called "a fling," per E! News, so it's possible she was just having some flirty fun.

Whatever Madonna's intentions were, nothing ever happened between herself and Andrea Denver. During a 2021 episode of "Watch What Happens Live," Denver gave viewers some insight into his relationship with the Grammy award-winning singer. "We became friends [after she posted my photo] after that, and she's the best," revealed Denver. Andy Cohen pried further, asking, "Hold on, excuse me, you must have taken her as a lover at one point?" However, Denver didn't budge. [Madonna] is beautiful, but I usually like ... a little bit younger," shared Denver. As for how they met? Denver appeared "briefly" in Madonna's "B****, I'm Madonna" video.

Even though it doesn't appear that Denver is into Madonna in that way, he did reveal in a 2022 interview with "Behind the Velvet Rope" that they were friends. "We chat for awhile, and I gotta say ... it's always really nice conversation," shared Denver. "We talk about many things, we talk about Italy, because she's a great mom to her children." The reality star also shared that Madonna's given him "so many advices" over the years, although he regrets not always taking heed to them.