No matter how you want to look at it, Madonna has remained one of the most interesting individuals of her time. She is a woman whose life is full of variety whether you want to look at her professional life or her personal life. The Madonna dating story also tells a lot about her taste in variety. This is not only with the number of men she has dated thus far but also with how they are almost all from different worlds.
Born on August 16, 1958, the musician, songwriter, actress, and businesswoman has almost touched the two ends of the world as far as dating is concerned; having been married twice, she has gone out with close to 50 men – or that is how it is rumored.
Madonna Dating Timeline and Relationship History
The Madonna dating timeline stretches back to 1972 when she got into a relationship with Wyn Cooper. Her relationship history would continue for many years to come. She has been involved with men of all races who are both older and younger and has dated someone at almost every step of the way.
Even though she has been more popular with men, the Queen of Pop was also linked to a number of women in the past. Beyond everything else, she had tried settling down a couple of times, but she did not succeed.
The irony, however, is that the woman who seems never to age, would not only go on to date many, but she would also leave many feeling used and dumped, and leaving many more to wonder which was love and which was lust.
Her Husbands
As stated, Madonna has been married more than once in her life thus far. The first time she got married was as far back as 1985 when she tied the knot to American actor and filmmaker Sean Penn. Before settling down with him, the Queen of Pop had her reservations most especially because she felt the two of them were too similar in many ways including their harsh temperaments; nonetheless, she still went ahead to marry him.
Just 4 years down the line, Madonna and Penn who was said to be hated by many people close to the singer went for a divorce marking the end of their marriage. One of the things said to have led to the end of the union apart from their similarities was the jealousy of Penn as well as his many legal issues.
Although he would go on to marry again and get divorced for the second time, the two-time Oscar winner revealed in 2018 that he was still very much in love with Madonna.
The next time that she would get married was in 2000 to film director and producer, Guy Ritchie after they first met in 1998 at dinner. Soon, they got engaged and had a large wedding only 3 days before Christmas. In 2004, the celebrity power couple renewed their vows, but the renewal would only be for the next 4 years as the marriage was already over by 2008.
Their union was blessed with a son, Rocco Ritchie who was born before the couple got married in 2000 and they also adopted another – David Banda.
Past Boyfriends and Girlfriends
As a very young woman, the 1970s saw the iconic singer dating men including Russell Long who was her high school sweetheart to whom she lost her virginity when they were still both teenage kids younger than 17. She would be linked later in 1976 and 1977 to Christopher Flynn and Mark Dolengowski respectively. Norris Burroughs and Patrick Hernandez were other men in the line before she went out with Dan Gilroy from 1979 to 1980.
From 1980 to 1982, she went out with Stephen Bray, followed by Mark Kamins, Ken Compton, and then Jellybean Benitez from 1982 to 1985. It was after this relationship ended that she got married to Sean Penn. In 1972, she was linked to John F. Kennedy Jr.
Following the end of her marriage, Madonna got linked to Warren Beatty from 1989 to 1990, followed by Tony Ward in 1990, then Jose Canseco in 1991. Vanilla Ice was to follow for a year, and then she would have a relationship that would last from 1991 to 1994. From 1992 to 1994, she was said to be in yet another relationship with Ingrid Casares, which is among her most popular lesbian relationship.
With some more people in the line including Japanese-American model and actress Jenny Shimizu whom she dated in 1994, she went on to date rapper Tupac Shakur. The relationship didn’t last as it would later be revealed that Shakur dumped her for being white.
Still, in 1994, the singer dated basketball all-time bad boy, Dennis Rodman with whom she tried to have a child, but it didn’t work. Two years later, she was down with Carlos Leon with whom she had a daughter, Lourdes Leon who was born in 1996. Andy Bird and Chris Paciello were the next men she dated before meeting her next husband, Guy Ritchie.
She found herself in the arms of a much younger lover, Jesus Luz in 2009 after the end of her marriage. At the time, she was 50, while Luz was only 22. What made their relationship more surprising was that the mother of Luz was only 37 at the time, much younger than Madonna. The Brazilian model was replaced with a slightly older model Adam Senn in 2010.
The Madonna Dating story continued after 2010 with some more young lovers including her former dancer, Brahim Zaibat whom she dated from 2010 to 2013, and then Timor Steffens from 2013 to 2014.
Aboubakar Soumahoro was the man she went on to date in 2016, before dumping him for Kevin Sampaio in 2017.
