Madonna’s Thirst For True Love & Lust: Two Marriages, Dating Still Going On

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Madonna's love story

Some people are born to give us great love stories and some are born to love greatly. Madonna, the Queen Of Pop falls into the latter category. If you want to know how much she loves greatly then you have to read Madonna’s Love story & relationship timeline below. Madonna started dating in 1979. And dating is going on. The romantic difference is she is the same but her dating partner is changing.

Do you believe that love can truly happen only once or it can happen many times? If love happens any times is it just infatuation or unconditional and giving love? Would you rather have one lover or many over different points in time?

Was Madonna truly in love? Who was her greatest love? Does she love or use and throw her partners? Was she only loyal to her own self? Find the answers below!

Who is Madonna?

Madonna's love story

When you hear the name, Madonna, only one person pops into your head, yes, the ‘Queen of Pop‘. Madonna’s full name is Madonna Louis Ciccone, an American singer, songwriter as well as an actress.

Madonna is one of the most celebrated artists of the 20th and 21st centuries, known for her versatile and revolutionary music, visual representation, and music production.

She was born in 1958 in Michigan. Some of her hit albums include Confessions On A Dance Floor (2005), True Blue (1986), MDNA (2012), Like A Virgin (1984), Ray of Light (1998), etc. Madonna has won 7 Grammy awards out of 28 Grammy nominations. It is time to read Madonna’s Love story & relationship timeline.

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Madonna’s love story with Dan Gilroy ended due to her career (1979)

Madonna met her first boyfriend, Dan, at a party in 1979. They lived in an abandoned synagogue with Dan’s brother, Ed, in Queens, New York. Her relationship was very special with Dan; you ask how? Well, read below.

Dan was the person who ignited the passion for singing in Madonna’s burning heart. After putting a guitar in Madonna’s hands, she started to give less time to her dance classes and devoted herself to singing.

Soon her hard work paid off, and she was called upon by Patrick Hernandez to be his background dancer as well as a singer! But this meant she had to go far away from Dan.

However, Dan kept everything cute and light by sending her really funny letters, making them look like they were from the President of America by painting the American flag on them and asking her to return to America. This kept Madonna going.

Eventually, Madonna fell sick with pneumonia, and she came back. She started playing drums for Dan and Ed’s band called The Breakfast Club. Soon she wanted to sing for the band but was not allowed.

This cracked her relationship with Dan, and she left him and his band. She felt loved by them, but her passion and ambition to have commercial success took her to greater heights, away from her first love.

Madonna dated 2nd boyfriend Jean Michel in 1982

In 1982, Madonna met a deeply talented artist named Jean. They soon developed a relationship with each other. Madonna adored Jean with all her heart and loved his passion for painting.

Once, Madonna recalled that she would wake up in the middle of the night or just at the break of dawn to not find Jean on the side of her bed but painting a canvas in their room. This moved her so much.

She loved the fact that Jean created art whenever he felt like it, no matter what time it would be. However, she had to end her relationship with him because of his drug addiction, which sadly took his life in 1988.

When they broke up, Jean demanded that Madonna return all the paintings he gave to her, and when she did, he painted them all black, signifying the dark end of their beautiful love story.

Madonna’s love story ended with 3rd boyfriend DJ JellyBean when she cheated on him (1983-1985)

Madonna started dating the DJ John JellyBean Benitz in 1983. They even produced a song together named Holiday. Both of them were going through an incredible love life when Madonna messed everything up.

You ask how? Well, she cheated on John with Steve Neumann, a journalist who was dating her friend Erika Belle at the time. This broke their relationship in 1985.

Their friends thought that they shared a great relationship, but at the same time, Madonna had control over everything; she was a diva who demanded constant attention and wanted things her way. Don’t you think Madonna’s Love story & relationship timeline is very strange?

Madonna married 5th boyfriend Sean Penn in 1985 & divorced in 1989

Madonna's Love story & relationship timeline

Sean and Madonna met on the sets of the Material Girl music video in 1985. They instantly had a romantic connection and married each other within six months! However, things started to go downhill from there.

Downhill, how? Well, it won’t be wrong to say that Sean, as a husband was jealous of any man who would even talk to Madonna. Their relationship started going down the drain when Sean attacked David Wolinski, a songwriter, for just talking to Madonna.

He was fined 1000 dollars for this misconduct, which left Madonna so upset. Four months later, he got into a fight with two photographers and was so jealous of Nick Kamen because he was working with Madonna.

Sean thought that the two of them were having an affair even when Madonna told him that they were not. This led to Madonna soon realizing that they were not in a happy marriage and there was just too much pressure.

So, she filed for a divorce in 1987 but also withdrew it, but she filed for it finally in 1989 for good. However, now the couple is really friendly, and in 2015 Madonna even said that she still loves Sean.

Madonna dated 6th boyfriend Warren Beatty in 1989

Warren and Madonna met on the sets of the movie Dick Tracy in 1989. He was in so much love with Madonna and loved everything about her. He thought of her as a spectacular dancer and a global phenomenon.

Madonna was also shooting her documentary called Truth and Dare at that time, and Warren told her that he did not want to be in it, to which Madonna replied that why would even she want him in it too.

Soon after the movie was released, the 21 year older boyfriend, Warren, and Madonna broke up with each other due to different opinions on the lifestyle, publicity, and fame.

Madonna dated 7th boyfriend Jim Albright in 1991

Jim Albright, Madonna’s ex-bodyguard in 2001, revealed that he had a three-year-long secret relationship with the queen of pop. It was a secret because he was her bodyguard and also had a girlfriend.

But in no time, Jim broke up with her girlfriend to be close to Madonna, and he also resigned as her bodyguard in 1993, which made Madonna talk to him every single day.

They got really serious and wanted to marry each other, but Madonna wanted him to sign a prenup, and he refused. The sad part is that Madonna, throughout their relationship, had affairs with countless celebrities and athletes.

After some time, when Jim told her that he hooked up with some other girl, Madonna simply dumped him and ended their relationship. She told him that she had never been loyal to a single man, that she was only loyal to herself.

Madonna dated 8th boyfriend Vanilla Ice in 1991 & ended due to ex-husband Sean Penn

Madonna started a relationship with the rapper Vanilla Ice in 1991. She was nine years older than him, and they used to have good fun together. Vanilla Ice recalled that they used to go out on dates after disguising themselves like other people.

They were in love, and Madonna wanted to get married to him, but Vanilla sensed something wrong. He realized that she had this neverending sense to get married and was impatience about it.

He was into her, but she was not still over her ex-husband Sean Penn and she even let this secret out to him, so they just ended their relationship because what’s the point, right? If you are not into it, leave it. One of the craziest parts of Madonna’s love story & relationship timeline, right?

Madonna romanced with 9th boyfriend Tupac Shakur in1993

Madonna's Love story & relationship timeline

It was mostly a rumor in 1993 that the biggest music stars were dating each other, but it was finally revealed in a letter that Tupac wrote to Madonna that they were indeed in a relationship.

Tupac revealed to Madonna through his letter that he wrote to her from jail that her comments hurt him and cut him deep like a knife, but he also apologized to her for not being a good friend to her.

He emphasized the fact that dating a black man would not harm her image publicly in any way, but his dating a white pop star would make his community question his image, a community he lives for. This was a very sad revelation and made many hearts ache.

Tupac urged her to understand that he could not clarify this to her during their break up as he was very limited in his experience as a young man who was in a relationship with an infamous sex symbol. Undeniably, the letter showed how he grew mentally and spiritually.

Madonna broke up mutually with her 10th boyfriend Carlos Leon in 1994

Madonna's love story

Madonna and Carlos met each other in the most unique way possible. They were jogging when their paths crossed in 1994 and Madonna thought it was her old flame, Jim Albright. She even sent people to him to know who he actually was.

Carlos was a personal trainer and he was not used to so much attention from the media. In 1995 Madonna while filming her film Evita realized that she was eleven weeks pregnant with her first child.

Carlos and Madonna even announced on her 37th birthday that they want to become parents. In 1996 Madonna’s first baby was born and it was a girl. She was named Lourdes Lola Maria Ciccone Leon.

The couple made a real effort to make their relationship work but they realized that it was better to separate and co-parent Lourdes and that’s what they exactly did!

Madonna married Guy Ritchie & divorced him due to fame (1999-2007)

Madonna's Love story & relationship timeline

Guy and Madonna met at their mutual friends’ party in 1999. He was the first guy to ever make Madonna’s head spin around completely. She just loved the way he carried himself and his confidence.

But Guy was not as into her as she was. This led to an on and off again relationship between the two for a while, until Madonna gave birth to her second baby with Guy in 2000, a boy, named Rocco Ritchie.

The couple got married in 2000 when Madonna accidentally found a crumpled paper bag with a ring and card in it. It was from Guy and touched her heart. Then they got married in Skibo Castle in Scotland.

But things were not so smooth for the two and they filed for divorce in 2007. Madonna was allegedly cheating on Guy emotionally with Alex Rodriguez. It was not the only reason though.

Guy wanted a quiet and simple life but Madonna wanted to glimmer in the limelight all the time. She would force him to come to things but he just did not want to.

They were only coming together for cameras while living separate lives and different lifestyles so in the end the best thing for them to do was divorce each other. Later it was also revealed that Madonna only shared a friendly connection with Alex and they were not involved romantically.

Madonna’s love story with her boy toys (2010-2022)

After her breakup, Madonna started a relationship with Brahim Zaibat, a French model and dancer. He starred as a model in Madonna’s Material Girl clothing line. Brahim was never stressed about being with Madonna as he treated her like any other woman, before taking her in as a world-class famous queen of pop.

They broke up in 2013 due to their busy schedules. In 2014, Madonna started dating Timor Steffens, a choreographer, who was thirty years younger than her. He saw Madonna as a strong woman who did not need to be mainstream to express her opinions. Their relationship ended in a couple of months.

In 2019, Madonna developed a romance with her tour choreographer Ahlamalik Williams, 36 years younger than her. They shared a stable relationship and also spent time with Madonna’s children. They broke up in 2022.

Madonna’s latest love flame, Josh Popper (2023)

Madonna's Love story & relationship timeline

Josh Popper is a famous professional boxer and boxing coach who just recently started dating Madonna in 2023. He is thirty-six years younger than Madonna and often shares glimpses of their romance on Instagram.

Before Josh, it was believed that Madonna dated Andrew Darnell for a couple of months. But right now Madonna is with Josh Popper. Do you think this could be an end to Madonna’s love story and relationship timeline?

Madonna’s love story gave her six beautiful children

Madonna's Love story & relationship timeline

Lourdes Lola Maria Ciccone Leon was Madonna’s firstborn baby. She had her with Carlos Leon in 1996. She is a very successful model now, modeling for SAVAGE X FENTY, Burberry, Mark Jacobs, etc. Often she laughs about the fact that she inherited her mother’s control issues.

Rocco Ritchie was born in 2000 to Madonna and Guy Ritchie. He is a model and actor now. Guy and Madonna adopted David Banda, their second child together. Madonna believes that David has most of her DNA and she relates to him the most.

Chifundo Mercy James was adopted by Madonna as a single mother after her divorce from Guy in 2009. Madonna believes that Mercy is the kindest and most thoughtful person on the planet.

In 2017, Madonna adopted her twin daughters, Stella and Estere. They fit in like they were already there in the family. Madonna is a great mother and she just makes sure that her baby girls know that she is their mother and nothing will change that.

FAQs

How many marriages has Madonna had?

Madonna has only married twice. She met her first husband Sean Penn in 1985. They instantly had a romantic connection and married each other within six months! She met her second husband Guy Ritchie in 1999 and married him in 2000 In Scotland.

Who are Madonna’s ex-husbands?

Sean Penn and Guy Ritchie are Madonna’s ex-husbands. She divorced Sean in 1989 because of their endless fights and his toxic behavior toward her. Madonna divorced Guy in 2008 because of their different lifestyles and ost connection.

Who was Madonna’s first husband?

Sean Penn was Madonna’s first husband. Sean and Madonna met on the sets of the Material Girl music video in 1985. They instantly had a romantic connection and married each other within six months!

Who was Madonna’s greatest love?

Sean Penn is Madonna’s greatest love. So, she filed for a divorce in 1987 but also withdrew it, but she filed for it finally in 1989 for good. However, now the couple is really friendly, and in 2015 Madonna even said that she still loves Sean.

Who is Madonna in a relationship with?

Madonna is in a relationship with Josh Popper. Josh Popper is a famous professional boxer and boxing coach who just recently started dating Madonna in 2023. He is thirty-six years younger than Madonna and often shares glimpses of their romance on Instagram.

Did Tupac and Madonna date?

Yes, Tupac and Madonna dated in 1993. It was mostly a rumor in 1993 that the biggest music stars were dating each other, but it was finally revealed in a letter that Tupac wrote to Madonna that they were indeed in a relationship.

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Thoughts on Madonna’s Love Story & Relationship Timeline

If your head is spinning after learning all the love stories of Madonna, trust me you are not alone. It seems like Madonna never really starts a relationship with the thought of making it last forever but rather enjoying the relationship at the moment.

She probably loves to love. Madonna is not scared to get the guys she wants or stop loving someone just because her heart is broken. Her concept of love is really different than the norm just like her entire existence.

We can learn to put ourselves first in a relationship and then go through things that might hurt our hearts. It is okay to be selfish and love unconditionally. It is important to stay loyal to yourself always. Give me your thoughts on Madonna’s Love story & relationship timeline in the comment box.

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