Madonna Dating Timeline, Relationship History, Past Boyfriends and Husbands

Whichever way you look at it, Madonna has remained one of the most interesting personalities of her time. She is a woman whose life is very varied, whether you look at her professional or private life. The Madonna dating story also tells a lot about her taste for variety. This is not only because of the number of men she has dated so far but also because almost all of them come from different worlds.

Born on August 16, 1958, the musician, songwriter, actress, and businesswoman has almost touched both ends of the world when it comes to dating; she has been married twice and dated almost 50 men – so they say.

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Madonna dating Timeline and Relationship History

The Madonna dating dates back to 1972 when she entered into a relationship with Wyn Cooper. Their relationship was to last for many years. She was involved with men of all races, both older and younger and met someone at almost every step of the way.

Although she was more popular with men, the Queen of Pop was also associated with a number of women in the past. Above all, she had tried to settle down a few times, but she did not succeed.

The irony, however, is that the woman who never seems to age not only dates many women, but also leaves many feeling used and dumped, and many others wondering what love and lust is.

Her Husbands

As already mentioned, Madonna has been married more than once in her life. The first time she got married already in 1985 when she made the alliance with the American actor and filmmaker Sean Penn. Before she settled down with him, the Queen of Pop had her reservations mainly because she felt that the two were too similar in many ways, including their rough temperament; nevertheless, she wanted to marry him anyway.

Only four years later, Madonna and Penn, who was said to be hated by many people close to the singer, divorced, which meant the end of their marriage. One of the things that, apart from their similarities, is said to have led to the end of the marriage was Penn’s jealousy and his many legal problems.

Although he would remarry and divorce for a second time, the two-time Oscar winner in 2018 revealed that he still loved Madonna very much.

The next time she married the film director and producer Guy Ritchie was in 2000 after they met at a dinner in 1998. Soon afterward they got engaged and celebrated a big wedding just 3 days before Christmas. In 2004 the prominent power couple renewed their vows, but the renewal was only for the next 4 years, as the marriage had already ended in 2008.

Their union was blessed with a son, Rocco Ritchie, who was born before the couple married in 2000, and they adopted another – David Banda.

Past Boyfriends and Girlfriends

As a very young woman, the famous singer went out with men in the 1970s, including Russell Long, her high school sweetheart, to whom she lost her virginity when they were both teenagers under 17. Later in 1976 and 1977, she was associated with Christopher Flynn and Mark Dolengowski respectively. Norris Burroughs and Patrick Hernandez were other men in the line before she dated Dan Gilroy from 1979 to 1980.

From 1980 to 1982 she dated Stephen Bray, followed by Mark Kamins, Ken Compton, and then Jellybean Benitez from 1982 to 1985. After this relationship ended she married Sean Penn. In 1972 she was married to John F. Kennedy Jr.

After the end of her marriage, Madonna was joined by 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 had a relationship that was to last from 1991 to 1994. From 1992 to 1994 she is said to have had another relationship with Ingrid Casares, which is one of her most popular lesbian relationships.

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With a few more people in the series, among them the Japanese-American model and the actress Jenny Shimizu, with whom she was together in 1994, she went out with the rapper Tupac Shakur. The relationship didn’t last long, because later it should turn out that Shakur had left her because of her white skin color.

Nevertheless, in 1994 the singer arranged to meet the basketball villain of all time, Dennis Rodman, with whom she tried to have a child but it didn’t work out. Two years later she was with Carlos Leon, with whom she had a daughter, Lourdes Leon, born in 1996. Andy Bird and Chris Paciello were the next men she met before she met her next husband, Guy Ritchie.

In 2009, after the end of her marriage, she found herself in the arms of a much younger lover, Jesus Luz. She was 50 years old at the time, while Luz was only 22. What made their relationship even more surprising was that Luz’s mother was only 37 years old at the time, much younger than Madonna. The Brazilian model was replaced in 2010 by a slightly older model Adam Senn.

The Madonna dating story continued after 2010 with several other young lovers, including her former dancer Brahim Zaibat, with whom she dated from 2010 to 2013, and then Timor Steffens from 2013 to 2014.

Aboubakar Soumahoro was the man she was in 2016 before dumping him in 2017 for Kevin Sampaio.