Madonna’s Impressive Dating Resume: From Artist To President

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Madonna’s Impressive Dating Resume: From Artist To President

Madonna’s Impressive Dating Resume: From Artist To President

Madonna has been in the spotlight not only for her great performances as a music legend but also for her romantic relationships.

He has been linked to several high-profile partners over the years, including Dennis Rodman, Warren Beatty, and the late Tupac among others. After being openly with men for most of her life, Madonna caused a stir in fans in October 2022 when she created a TikTok video that seemed to imply she was coming out as gay. That’s as far as the latest details about his sexuality as he doesn’t discuss his sexuality directly.

As her Celebration Tour prepares to take the world by storm, let’s take a look at everyone who dated Madonna throughout her illustrious career.

Jean-Michel Basquiat

Madonna had a short-lived relationship with artist Jean-Michel Basquiat in 1982. She admired his dedication to painting but stated that their relationship ended due to Basquiat’s struggle with addiction. Tragically, Basquiat died in August 1988 at the age of 27 due to a battle with addiction.

And Gilroy

Dan Gilroy attended the premiere of 'Velvet Buzzsaw' in Los AngelesMEGA

Shortly after Gilroy and Madonna met at a party in 1979, they began a romantic relationship. Within months, the “Ray of Light” singer, who was an inspirational dancer at the time, became a regular face at the synagogue where Gilroy lived with his brother, Ed Gilroy, in Corona, Queens.

During their time together, Dan and Madonna worked together for about a year, where he was the drummer for their band, the Breakfast Club. Her strong desire to sing in the band caused tension between her and Dan, and it also strained the relationship between the Gilroy sisters. In the end, she chose to leave the group and her relationship with Dan so that she could pursue her singing career fully.

Sean Penn

Sean Penn and Madonna JoggingMEGA

Madonna and Sean began dating in February 1985 after meeting on the set of the famous “Material Girl” music video. They married on the “Like a Prayer” singer’s 27th birthday in a beautiful Maui wedding, just six months after they first met. Their marriage was marked by turmoil, with early signs appearing in April 1986 when Sean attacked songwriter David Wolinski for talking to his wife.

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After several years he entertainer “4 Minutes” finally gave in to the challenge, and filed for divorce on December 4, 1987, which he reportedly asked to withdraw less than two weeks later.

However, the pop star put her foot down and filed for divorce again in January 1989. Since then Madonna and Sean have remained friendly, and in December 2016, the artist admitted she was “still in love” with her ex-husband, even offering to remarry him if he bid $150,000 in a charity auction.

John “Jellybean” Benitez

In 1983, Madonna began dating DJ John “Jellybean” Benitez, who eventually produced the 1983 hit “Holiday.” They initially had a strong relationship and even reportedly got engaged and moved in together. However, their relationship faced turmoil when the Grammy Award winner was allegedly involved with journalist Steve Neumann, who was in a relationship with her friend, Erika Belle. Their romance ended in 1985, around the same time Madonna met Sean Penn.

Josh Popper

Madonna’s involvement with the boxer became apparent in a photo she shared on Instagram on February 12, 2023. One photo shows the pop star with the boxer and his trainer after he won a match at Gleason’s Gym.

Speculation intensified after the “Dangerous Game” star showed — sharing an image — her support by attending another Josh boxing match on March 3. To date, neither Madonna nor Josh have made any public statements regarding their rumored relationship. .

Vanilla Ice

Ais Vanila performed during 'I Love The 90's' at the SSE ArenaMEGA

Madonna began dating rapper Vanilla Ice in 1991, and their relationship ended after eight months. In an October 2021 interview, Vanilla claimed that her ex-flame actually proposed to her during their relationship. He mentioned that he felt he was too young to marry at the time and wasn’t ready for it, although he found Madonna to be a sweetheart, and they had fun together.

Ritchie’s man

Guy Ritchie and Madonna enjoy a night at Volstead NightclubMEGA

The singer and the director met in 1999, and started a romantic relationship – albeit on-again-off-again -. In March 2000, they announced that they were expecting their first child together and their son, Rocco Ritchie, was born on August 11, 2000. The couple eventually married on December 22, 2000, in a private ceremony at Skibo Castle in Scotland. Despite their initial attraction, their marriage faced difficulties, leading to the announcement of their divorce in October 2008.

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Warren Beatty

Warren Beatty and Madonna pictured together on 01 Jan 1990MEGA

Madonna and Warren met while working together on the film “Dick Tracy” in 1989, and they dated for about 15 months starting in 1990. During their relationship, they initially disagreed about Beatty appearing in the documentary “Madonna: Truth or Dare.”

In the end, Warren agreed to be in the documentary but on the condition that it allowed him approval over the footage used. Unfortunately, their relationship fell apart after the release of “Dick Tracy,” mainly due to their differences over exposure and public fame.

Jim Albright

Although Madonna’s relationship with her former bodyguard had its ups and downs, the two grew closer when Jim left his position as her bodyguard in 1993. In fact, the only reason they didn’t exchange vows, even though they considered marriage, was because of Madonna’s insistence on a prenup .

As their romance faded, Jim claimed that his then-girlfriend had cheated on him with other celebrities, including Sandra Bernhard and Ingrid Casares. Although the famous songwriter was said to be unfaithful, it was reportedly Jim’s confession with another person that caused their relationship to end.

Tupac Shakur

TUPAC SHAKUR wears gold jewelry and a red sweater in the colors of the Georgia gangster 'Bloods'.  03 June 2003MEGA

Madonna briefly met the famous rapper after introducing actress Rosie Perez at the 1993 Soul Train Awards. However, their romance was short-lived, with the late Tupac explaining the reason for ending the relationship in a letter to the singer written in January 1995.

Dennis Rodman

Dennis Rodman attends the 19th Annual Harold & Carole Pump Foundation GalaMEGA

Madonna met Dennis briefly in 1994. Although their relationship was short-lived, Dennis wrote about it lovingly in his 1996 memoir, “Bad as I Wanna Be.”

Carlos Leon

Madonna crossed paths with personal trainer Carlos Leon in 1994 when he jogged past her in Central Park. Although Carlos reportedly struggled with the media attention that came with dating the iconic singer, the two were romantically involved.

The couple welcomed their first and only child together, daughter Lourdes “Lola” Maria Ciccone Leon, on October 14, 1996. Sadly, their relationship ended in May 1997.

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Brahim Zaibat

Madonna began dating the French dancer and model in September 2010, and they were in a relationship for three years. During that time, they shared moments such as a visit to Paris and his performance during his 2012 MDNA tour. They also appeared together on the red carpet at the 2013 Met Gala. However, their relationship ended in December 2013, with “busy schedules” cited as the reason for the split.

Timor Steffens

Timor Steffens arrives at the MTV European Music Awards in RotterdamMEGA

After her split from Brahim, Madonna had a short “courtship” with Timor in 2014. The choreographer, who is much younger than the founder of Maverick, openly discussed their relationship with The Mirror. However, their romance didn’t last long, and they reportedly broke up shortly after Timor spoke to the outlet.

Ahlamalik Williams

Madonna and boyfriend Ahlamalik Williams leave the Grand Rex in Paris.MEGA

Madonna’s relationship with the dancer and choreographer, who is 36 years her junior, first gained attention in June 2019. It happened when she posted an Instagram video of them dancing to celebrate her album, “Madame X,” topping the Billboard charts. .

Although the Guinness World Record holder and Ahlamalik maintained a relatively low-key relationship, he was a prominent presence in her life and featured in her Instagram posts until 2021. Reports indicate they split in April 2022 after three years together.

John F. Kennedy Jr.

Madonna is rumored to have had flirtatious interactions with John in the 1990s, with them engaging in playful and irreverent conversations over faxes and phone calls. Although they make several attempts to meet, their busy schedules and distance present challenges, so their relationship remains on a flirtatious and friendly level without developing into a full-blown romance.

Tony Ward

Tony Ward and Madonna pictured together in 1991MEGA

In 1990, the New York City native dated actor and model Tony Ward, who appeared with her in the “Justify My Love” music video. PEOPLE reported that in 1991 Tony seemed to have broken up with Madonna at the same time that he married his old flame, Amalia Papadimos, in a hasty Las Vegas ceremony on August 21, 1990. He is still dating the “Who’s That Girl” actress ” at that time.

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