Most modern followers of Madonna have a hard time recalling all of her past relationships. After all, she has a long history of dating plenty of famous and not-so-famous men. In recent years, she's also been dating younger and younger men. But back in 1985, Madge was married to Sean Penn, who was, at the time, another Hollywood great. The two were married for less than four years, with two divorce filings and a court case at the end. But to this day, both seem to have a sweet spot for each other, making fans wonder whether they'll ever reconnect.

Madonna And Sean Penn Divorced And Wound Up In Court

Madonna and Sean seemed like a perfect match when they got married on her birthday in 1985. Madonna was quoted as saying their temperaments were similar and that they were as close as siblings.

While that gave some 'ick' vibes, Madonna seemed to be saying that the two had a lot in common, and while she acknowledged at the time that it might not work it, the wedding went full speed ahead.

The long-forgotten details of Madonna and Sean's relationship include intense jealousy from Sean, accusations that Madonna cheated, and one divorce filing before they actually separated.

Related: Why Charlize Theron Was Absolutely Furious About Her Break Up With Sean Penn

But by the time they split, Madonna had accused Sean of assault — though she later dropped the accusation. In fact, after they divorced, they seemed to be on good terms.

Then, almost three decades later, Sean attended one of Madonna's concerts, then hinted he still had feelings for her.

Despite Being In Many Other Relationships, Sean Says He Still Loves Madonna

After divorcing Madonna, Sean dated a number of other stars, and later married and divorced twice more. And while many rumors swirled about the nature of his relationships, Yahoo! says that one of his marriages, to ex Robin Wright, was "turbulent" but didn't lead to abuse charges like Madonna's.

After separating from Robin (they married in 1996 and divorced in 2010), Sean wound up married again in 2020.

He and Leila George divorced in 2022.

Related: The Real Reason Sean Penn And Leila George Got Divorced

Sean, for his part, admitted that he was still in love with Madonna in an interview on The Late Show with Stephen Colbert. On the show, he said, "I love my first wife very much." He even elaborated, "I'm a Madonna guy."

Though the second part could have referred to her music, the first part of his statement was very clear in how he feels about Madonna. For her part, Madonna spoke about Sean during a concert, when she talked about how he'd attended a concert of hers ages ago, while they were married.

Her opinion at that point was that thirty [expletive] years later, Sean was willing to support her music.

Sois there a chance the two will ever reconcile?

Will Madonna And Sean Penn Ever Get Back Together?

Though they seem to be on decent terms these days, it appears unlikely that Sean Penn and Madonna will ever get back together.

After they broke up, Madonna dated Carlos Leon and had their daughter Lourdes. After their breakup, she married Guy Ritchie and they had a son together.

Madge and Sean had multiple periods where their singledom overlapped, and it does appear that Madonna is more into casually dating these days—so there's a question of why they haven't reconnected given that they still seem to share feelings.

It may just be that though they get along, they realized they made better friends than partners. There's also the fact that Sean says he's still in love with his most recent ex, Leila George.

Related: How Does Vincent D'Onofrio Feel About Sean Penn Marrying His Daughter?

People reported after their divorce that Sean stated he was still "so in love" with Leila, admitting that he wasn't a good husband to her.

Penn stated that he'd been abusing alcohol and substances, trying to find an escape from bad things going on in the world, and that it wasn't fair to Leila.

Of his ex, he said, "I know that this is my best friend in the world and definitely the most influential, inspiring person, outside of my own blood, that anybody could ask to have in their life."

Clearly, Sean isn't yet ready to move on. But who knows—maybe he'll reconnect with Madonna someday. Or, he might get back together with George; the two have been photographed together since their split.