Madonna was married to Sean Penn and Guy Ritchie, and her publicly reported relationships span several decades. There is no authoritative, complete list of everyone she has dated: some entries are supported by Madonna’s own comments or contemporaneous coverage, while others remain reports or rumors. The chronology below distinguishes those levels of certainty rather than treating every name as equally established.
Madonna’s marriages
Sean Penn
TIME identified Penn as Madonna’s boyfriend in a May 1985 profile. The magazine described her warmly calling out Penn’s name when asked about favorite actors. Parade reports that they met while making the “Material Girl” video, married in August 1985, and finalized their divorce in 1989. TIME’s 1985 profile and Parade’s relationship timeline document different parts of the story.
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Guy Ritchie
Parade reports that Madonna began dating the film director after they met in 1999, married in December 2000, and announced plans to divorce in 2008. Hollywood Life also describes their marriage as lasting from 2000 to 2008. Parade and Hollywood Life provide these reported dates.
Earlier relationships and reported partners
Dan Gilroy
Parade reports that Madonna met musician Dan Gilroy in 1979; they were bandmates and dated for about 18 months. In a 1984 Rolling Stone interview quoted by Parade, Madonna said, “It was one of the happiest times of my life,” and recalled, “I really felt loved.”
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Steve Bray
A May 1985 TIME profile calls musician Steve Bray a former boyfriend and notes that he made a demo tape with Madonna. The profile does not give dates for their relationship. TIME establishes the contemporary reference, but not its length or precise chronology.
Jean-Michel Basquiat
Parade reports that Madonna and artist Jean-Michel Basquiat briefly dated in 1982. Reflecting on the relationship in a 2014 Interview Magazine conversation, Madonna said, “Basquiat was my boyfriend for a while,” then recalled him painting in the middle of the night. The account and quotation are reproduced in Parade’s timeline.
John “Jellybean” Benitez
Parade reports that Madonna met DJ and producer John “Jellybean” Benitez in 1983. He produced “Holiday,” and the two dated for less than two years before splitting in 1985, according to the publication.
Rank #2
Warren Beatty
Parade reports that Madonna and actor Warren Beatty met while working on Dick Tracy, began dating in 1990, and split the following year. These dates come from Parade’s retrospective account, rather than a contemporaneous timeline.
Vanilla Ice (Robert Van Winkle)
Parade places Madonna’s relationship with musician Vanilla Ice, born Robert Van Winkle, between 1991 and 1992, lasting around eight months. In a 2013 recollection quoted by Parade, he described using disguises to go out together: “And we could walk in and the bodyguards would be like 20 feet behind, kinda looking like we’re nobody.”
Tupac Shakur
Parade reports that Madonna and rapper Tupac Shakur met in 1993 and dated privately until a split in January 1995, citing a prison letter later published by TMZ. Hollywood Life says Madonna confirmed the relationship during a 2015 appearance on Howard Stern’s radio show. The existence and details of the relationship are therefore supported by attributed reporting, but the chronology and letter’s account should not be treated as independently verified in every detail. See Parade and Hollywood Life.
Rank #3
Dennis Rodman
Parade and Hollywood Life describe a brief relationship between Madonna and basketball player Dennis Rodman in 1994. Stories about personal plans during the relationship come from Rodman’s memoir, so they are his account rather than established facts. Parade and Hollywood Life both report the link.
Carlos Leon
Madonna dated fitness trainer Carlos Leon from 1994 to 1997, according to Parade and Hollywood Life. Leon is the father of their daughter, Lourdes Leon. Hollywood Life also quotes Leon describing their continuing friendship in a 2008 interview. See Parade and Hollywood Life.
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Hollywood Life reports that Madonna dated aspiring screenwriter Andy Bird around 1997. Its account refers to a voicemail published by the Daily Mail; the relationship is best described as a reported link rather than a publicly established chronology. Hollywood Life is the source for this entry.
Rank #4
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Partners reported after Madonna’s marriage to Ritchie
Jesus Luz
ABC News identified Brazilian model Jesus Luz as a previous partner in a January 2012 account and said Madonna met him after her divorce from Ritchie. Hollywood Life places their meeting at a 2008 W magazine shoot and says they were together until around 2010. The publications provide the relationship context and approximate dates: ABC News and Hollywood Life.
Brahim Zaibat
In January 2012, ABC News described dancer Brahim Zaibat as Madonna’s then-current partner. Madonna told interviewer Cynthia McFadden, “I didn’t choose to, you know, I didn’t, like, write down on a piece of paper I’m now going to have a relationship with a younger man.” Parade reports that the relationship began around 2010 and lasted about three years. The interview and timeline are at ABC News and Parade.
Ahlamalik Williams
Madonna’s relationship with dancer Ahlamalik Williams is commonly placed in the late 2010s and early 2020s, but reports differ on its start. Hollywood Life says they began dating in 2018 and separated in spring 2022. Parade says they met on the Rebel Heart tour in 2015, became the subject of romance rumors in 2019, and split in 2022 after about three years. The publications do not settle one precise start date: Hollywood Life and Parade.
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Andrew Darnell
Hollywood Life reports that Madonna was linked to model and skater Andrew Darnell in 2022 and characterizes the connection as casual, citing unnamed sources. That description is the outlet’s account, not a public characterization from Madonna. Hollywood Life is the source.
Josh Popper
Parade describes Madonna’s 2023 connection with boxing coach Josh Popper as a rumored fling, noting public photos and a stage kiss. Those details do not, on their own, establish a confirmed relationship, so the link remains reported rather than certain. See Parade’s account.
Akeem Morris
Hollywood Life’s August 16, 2026 article calls Jamaican-born footballer Akeem Morris Madonna’s boyfriend. It reports that they met during a 2022 Paper magazine cover shoot and that public signs of romance appeared in summer 2024. Parade had said on June 5, 2025, that it was unclear whether they were still together at that time. The newer report makes Morris a recent reported partner, but the coverage cited here does not amount to direct confirmation from either person; the most precise phrasing is that they have been reported as a couple. See Hollywood Life and Parade.
How to read Madonna’s dating timelines
These names do not all have the same evidentiary footing. Penn and Ritchie were spouses; TIME and ABC News provide contemporaneous reporting or Madonna’s own words for specific periods; and several other relationships are described in retrospective entertainment timelines. For later links, the distinction between a reported relationship, a rumor, and direct confirmation matters. Public timelines also cover different date ranges and disagree on some chronology, notably Williams’s reported start date.
As a result, this is a sourced overview of publicly documented or reported partners, not proof of every relationship Madonna has had. It avoids assigning a total: no authoritative count of her past partners is established by the cited coverage.
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