How Many Times Has Madonna Been Married?

Madonna is one of the world’s biggest superstars, with a massive following of devoted fans. She has released hits such as “Like a Virgin,” “Vogue,” and “4 Minutes,” which are known and beloved by people everywhere.

She had also proven to be a savvy businesswoman and a master of reinvention, changing up her image over the decades to stay relevant and interesting as the music industry has evolved.

Still, one of the most interesting aspects of Madonna‘s public image is the relationships that she has had with famous men, including two husbands and a succession of boyfriends.

Madonna’s tumultuous first marriage

Madonna performs onstage
Madonna | Kevin Mazur/Getty Images for dcp

Madonna rose to fame in the early eighties after working as a model and waitress while trying to break into the industry. Her signature style, which included lots of lace, fishnet stockings, crucifix necklaces, and unkempt brows, caused thousands of young women to try and emulate her appearance, but Madonna seemed bent on doing things on her terms.

In 1985, she married iconoclastic actor Sean Penn. The two were tabloid darlings and were frequently featured on the covers of magazines. The whole world was interested in Penn and Madonna’s marriage, but things were definitely not peachy keen between them.

Their marriage was tumultuous and their arguments often made front-page news. Eventually, they divorced in 1989, but remain close to this day. In fact, Madonna even told Penn in 2016 that she was “still in love with him.”

Who was Madonna’s second husband?

Although her relationship with Penn might have been volatile, Madonna tied the knot again in the year 2000. This time, she walked down the aisle with director Guy Ritchie. By this time, she already had one child, a daughter that she had welcomed with her boyfriend Carlos Leon. Madonna and Leon broke up in 1997, leaving Madonna free to pursue a romance with Ritchie.

Ritchie and Madonna had one child together, a son named Rocco Ritchie. They were married until 2008 when they decided to get a divorce and went their separate ways. 

Madonna’s famous boyfriends

In addition to Carlos Leon, Madonna has dated a series of men that she never was engaged or married to. She is known for her habit of dating her background dancers, most notoriously her much-younger boyfriend Jesus Luz, whom she dated from 2008 until 2010.

While Madonna has received some criticism for her habit of dating younger men, she is not seemingly bothered by the negativity and keeps living her life the way that she wants to.

Madonna was in a high-profile relationship with baseball player Alex Rodriguez in 2008, immediately following her divorce from Guy Ritchie. She has also reportedly had brief relationships with Dennis Rodman, Tupac Shakur, Vanilla Ice, and playboy actor Warren Beatty.

There were also rumors that she went on a series of dates with Michael Jackson in the early nineties. 

Who is Madonna dating now?

These days, Madonna is enjoying a romance with another much-younger man Рher background dancer Ahlamalik Williams. Williams is twenty-five years younger than Madonna and has been working with the iconic singer since around 2015.

While Madonna doesn’t make it a practice to discuss her romantic relationships these days, the two have been pictured together several times, including one occasion where they were getting cozy on a hotel balcony.¬†

It is uncertain whether or not Williams’ and Madonna’s romance will last, but for the time being, she seems to be having fun. At the age of sixty-one, Madonna is still living on her own terms, and that includes how she chooses to approach romance.