Madonna's 15 Flings, Fellas, And Failures

Superstar Madonna has had more than her fair share of love interests since she’s been basking in the red-hot spotlight. Many a man (and a smattering of women) have gotten "Into the Groove", so to speak, with the pop icon, and if anyone’s "Living for Love", it’s Madonna.

Some of her hook-ups were short-lived, some even shorter-lived, and a few were lengthy enough to be considered “relationships.” While none have stood the test of time, to have had the chance to go "Deeper and Deeper" with Madonna is something all of her lovers are sure to remember vividly (or perhaps to tell their grandchildren about one day). That’s if they weren’t too scarred from "The Power of Good-Bye".

Now a 50-something broad, Madonna’s list of past loves is long, just like her remarkable decades-long career. Some of these tales of temptation were tame (for Madonna anyhow), some were a tease, and others were tumultuous. But leave it to the mystifying Madge to have a lover lineup that’s as diverse and surprising as her public antics.

Which past Madonna flame is your fave? There are so many good ones to choose from and these folks are only a sample of Madonna’s coital conquests. And the gal doesn’t seem to be slowing down – not in the music or the mating department. Stay tuned for the future flings Madonna is certain to command “Give it 2 Me,” even as she heads into her golden years – or in her case, as she nears her Ray of Light.

15 Jesus Luz

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The eternally youth-seeking Madonna, dated the much younger (and super-sexy) Brazilian model and DJ, Jesus Luz, from 2008-2010. The two met on a steamy photo shoot for W magazine, and as the cameras clicked, so did the hot-to-trot pair. It has been said that the Kabbalah-practicing Madonna introduced her young lover to the religion, although with a name like “Jesus,” one can’t help but notice the irony. Of course, like all of her other pairings, this relationship was not to be, but the two parted ways amicably. These days, Luz is signed to Ford Models and will no doubt look back on his short-lived fling with Madonna as the “good old days.” A cougar can only hang onto her cub for so long. Now Luz can sow his wild oats with other hot models and music industry insiders, though they won’t be able to get the senior-priced movie tickets on date night.

14 Sandra Bernhard

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The outrageous, outspoken, and out-there actress, author, and singer, Sandra Bernhard, is an open book about her bisexuality and pretty much everything else. One thing she’s discussed over the years is her past relationship with her longtime gal pal, Madonna. Apparently, the two were romantically linked back in the 1980s, although Bernhard may have crossed the "Borderline" with that fling. Whether Madge was just dipping her toe in the “lady pond” or had true feelings for Bernhard is something only the two of them know, although the ladies made for an unusual, yet somehow, perfect match. As you’ll read on, Bernhard will not have been the last lady that Madonna would "Live to Tell" about, and who knows if Bernhard was her first either? Certainly, a world of attention-seeking women came out of the woodwork claiming to have known Madonna when she was "Like a Virgin" to getting down with the ladies.

13 Alex Rodriguez

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Mid-2008 was a real home run for Madonna as she covered all the bases with famed Yankee slugger and noted ladies’ man, Alex Rodriguez. But not everything was a “grand slam,” as reports rumored that A-Rod, in true player fashion, was still married to his now ex-wife, Cynthia, while he was “stealing” Madonna away. Seems like the meddling Madge and the risk-taking Rodriguez didn’t mind the inconvenience of that little curve ball, since the pair was reportedly shopping for a home they were planning on shacking up in together. While the relationship eventually struck out, the two did make for an exciting pair while he still had his “ball” in her court. Perhaps there was some “foul” play involved that caused the relationship to slide into oblivion. At least we know that Madonna played the field as always with one of baseballs’ best. She probably even got free peanuts and Cracker Jack at all of his games.

12 Guy Ritchie

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Guy Ritchie and Madonna were husband and wife from 2000-2008. Ritchie is a British filmmaker (mostly crime flicks) with movies including Snatch, Mean Machine, Swept Away, Revolver, RocknRolla, and Sherlock Holmes under his likely high-priced designer belt. Ritchie met Madonna through some famous mutual pals (the musician, Sting, and his lovely wife of many years, Trudie Styler). Madge and her “Guy” married in Scotland and eventually had a son named Rocco together. These days, you can see the pair all over the tabloids fighting over custody of Rocco, as well as details on where the now-teenager lives. Eight years is a long relationship for the man-loving (and sometimes hating) Madonna, so Ritchie must be something super special. He’s since remarried and has a total of five children: Rocco, three with his current spouse, Jacqui Ainsley, and the child he and Madonna adopted while they were still hitched. Wonder if things in the bedroom with Ainsley is as spicy as they were with the seductive Madonna?

11 Carlos Leon

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Madonna dated the cool Cuban, Carlos Leon, the "baby daddy" of her daughter Lordes, from 1994 to 1997. Leon was a sought-after celebrity personal trainer when the two met, and then things got really personal (wink, wink). While the pair never made things official and got married, they had a steamy relationship that made Madonna feel like she was living on "La Isla Bonita". These days, Leon is an actor on the big screen and performing live on Broadway, residing in The Big Apple. He’s often spotted by the paparazzi doting on his now-grown daughter. He also has another child (a son) with his current wife, Benita Holte. His hot and handsome looks combined with Madonna’s unique and stylish presence made for a great genetic match for the lucky Lordes, who is now a college student and budding model. While Leon may no longer train celebrities, he sure trained Madonna on how to become a first-time mom!

10 Jenny Shimizu

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In the mid-1990s, Madonna dabbled with the dames once again and got together with the mysterious model, Jenny Shimizu. You may recall Shimizu also had a fling with the now-Mrs. Brad Pitt, actress Angelina Jolie. Shimizu claims that Madonna would fly her in, solely for a long-distance “booty call” no matter where she was in the world. Talk about “Flying the friendly skies!” This romance didn’t last long, but certainly placed Shimizu in a world of the high-style living and wild adventures. Madonna must have been intrigued by Shimizu’s photo spreads for her modeling campaigns for Calvin Klein, Prada, and Banana Republic. Since their split, Shimizu continued to model, and also landed movie gigs. She was also on America’s Next Top Model alongside the “smizing” Tyra Banks and appeared on Bravo as a judge on Make Me a Supermodel. Who knows if she and Madonna still connect, but today Shimizu is a married woman since her wedding to Michelle Harper in 2014.

9 Tupac Shakur

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May Tupac rest in peace, but while he was alive and well, he dated Madonna in 1994. While this romance between the pop star and rapper wasn’t well-publicized at the time, Madge revealed the sizzling information during an interview with “shock jock,” Howard Stern. While Madonna and Tupac made for a somewhat unlikely pair, both were super-famous at the time and everyone needs some love, right? However, their relationship wasn’t to be, or perhaps Tupac’s pals didn’t want it to last. Rumor has it that his friends encouraged him to ditch Madonna pronto. Who knows why, but apparently he followed their advice and set Madge free to continue to date and do her thing with the fellas who were to come after him. Madonna was no doubt shaken up about Tupac’s violent death just two years after their split. Had they still been an item, she’d have lost her man, not to mention a major force in the entertainment biz.

8 Warren Beatty

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Ah, good old Warren Beatty! Known for his wild womanizing ways, he’s now a faithful (we hope) husband to the talented and beautiful actress Annette Bening, and has four children. But back in the day (meaning most of his “courting” years), Beatty hooked up with more gorgeous gals than he could possibly keep track of. One of his leading ladies was Madonna, with whom he had a tabloid-tempting romance from the late 1980s through the early ‘90s. The “May-December” pair met on the set of the hit flick, Dick Tracy, and fantasy soon became reality for the actors. He was even spotted in Madonna’s stimulating tell-all, her Truth or Dare documentary, revealing the two were participating in a little "Hanky Panky". But as expected, Beatty and Madonna parted ways, allowing both to carry on with their serial dating ways. It was just a couple of additional notches on their exceedingly whittled away bedposts!

7 Sean Penn


One of Madonna’s more notorious fellas is actor Sean Penn, to whom she was married from 1985 to 1989. Their relationship was often tumultuous, and always in the limelight. While their movie together, Shanghai Surprise, was not a box office hit, the relationship was (at least for a while). She wanted to divorce him in 1987, but they stuck it out, only to finally split ways for good in ’89. The pair never had children together, but he did have two kids eventually. Penn married again, to the talented and attractive, Robin Wright, but they too ended up divorcing. Third time’s a charm, Sean? These days, Penn not only acts, but he’s a cutthroat political activist. He’s also still charming the ladies and recently dated (then broke up with) the glamourous actress, Charlize Theron. While there are those that may not find Penn to be the typical handsome actor type, he still exudes the charisma and sex appeal that keeps the ladies wanting more. There are still those that hope he and Madonna will get back together, especially since he was even spotted at one of her concerts recently.

6 Vanilla Ice

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Robert Van Winkle, AKA Vanilla Ice was one of Madonna’s many men, believe it or not. They dated briefly in the early 1990s, and Ice claims that Madonna was quite the exciting “older lover.” As exciting as the relationship may have been, the duo broke up after she released her Sex book. Perhaps Ice wasn’t so keen on such a hot publication, being “Ice” and all. Regardless of the reason for the split, it was evident that this romance wasn’t going to last. Ice is a one hit wonder and Madonna is a mega-star. Plus, with his prudish ways in regard to her Sex book, Ice may have been a little too “Vanilla” in the bedroom department for a wild child like Madonna. Although, it would have been fun if the two recorded a song together. Yet, Madonna did record "Frozen" in 1998 (perhaps that was an ode to her ex, Vanilla Ice)!

5 Dennis Rodman

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The idea of NBA star, Dennis Rodman, and Madonna dating is just so odd that it actually makes sense. Both are over-the-top eccentric, love the spotlight, and seem to be up for just about anything (including dating each another). Rodman and Madonna hooked up in 1996, and Rodman claims that Madonna wanted to have his “love child" (perhaps she was seeking tall offspring or trying to snag his athletic genes). As expected, this relationship was short-lived, but not as short as his drive-through Vegas marriage to the sexy, Carmen Electra. We don’t see nearly as much from Rodman as we had during his heyday, but with all those piercings, tattoos, and various hair colors, he’s certainly not hard to miss. Too bad his fling with Madge didn’t pan out. The two would have made for some interesting gossip and news items. But he “passed” Madonna to the next guy and “sunk his ball” in many gals since.

4 Britney Spears


“Oops, she did it again!” Madonna took another tempting taste of lady-loving with her infamous VMAs smooch with perky pop princess, Britney Spears, as they flounced around during a live performance of "Like a Virgin" with pop star Christina Aguilera back in 2003. The eyes-glued audience was shocked, but they weren’t quite sure what to make of the display. The sexy stage act was interesting, but odd, and everyone seemed to forget that X-Tina got a taste of Madonna’s tongue too. While Madonna and Spears were not actually romantically linked in the traditional way, they did have to rehearse the promiscuous performance before the big show, so there must have been some titillating games of “tonsil hockey” before lusciously locking lips for excited audiences worldwide. Spears and Madge seemed to enjoy the kiss and may have said "Gimme More" to one another, but the hook-up was for the performance only, not personal pleasure… or was it?

3 Henry Rollins


Back in the 1980s when Madonna was starting her career, she reportedly dated punk rocker, Henry Rollins of Black Flag and The Henry Rollins Band. Punk and pop don’t usually make musical magic, but hot young folks seeking a hook up see no genre. Seeing the two these days makes it hard to picture the two as a couple, but decades ago, Rollins and Madonna once had a flirtation for a while anyhow. Plus, Rollins is now a writer and activist, similar to Madonna, so perhaps they could have gone the distance if only they stuck it out in their youth. But the two needed to explore their love lives and careers before they could commit, so separation was inevitable. Whether or not the two followed one another’s career over the years is not certain, but surely they are proud of the one another’s accomplishments. Plus, Madonna’s butt still looks just as perky in those assless chaps she loves to sport as it must’ve been years ago!

2 John Kennedy Jr. 


Imagine Madonna as part of the iconic and beloved Kennedy clan. If things had worked out romantically for Madonna and John Kennedy Jr., who dated in 1997, the world would surely be a different place. But what would a journalist, magazine professional, and lawyer have in common with a pop goddess anyhow (aside from a mutual physical attraction)? Plus, would the often scantily-clad Madge really fit in to the New England conservative atmosphere that surrounds the Kennedys? Sure, Kennedy Jr. paved his own path, so a little grumbling from the family at large wouldn’t necessarily sway him, but perhaps the Kennedy sensibility seeped into his mentality subconsciously. Kennedy Jr. wound up marrying the lovely Carolyn Bessette (a woman seemingly more fitting for the debonair dude), but as we all know, the two tragically perished in a plane crash, along with Bessette’s sister. May they all rest in peace, but Madonna must think of what could have been every now and again.

1 David Blaine


No, it wasn’t an illusion. Madonna dated magician and master illusionist, David Blaine, for a brief stint in 1998. While Blaine may know Madonna’s "Secret" to her success, he couldn’t answer her call to "Rescue Me" from endless dating as well as he could escape from a Houdini-style compromised position. Too bad the two couldn’t "Keep it Together" for a longer period of time. With her musical talents and his knack for illusion, the duo could have taken that show on the road. But there was no “magic” between them and their affair was not to last. He just didn’t have that “spell” over the singer who seems to always seek the next best fella to pair up with. Romance wasn’t “in the cards” for these two, but he did find love again and has a child. At least Blaine didn’t go “poof” and make Madonna disappear altogether. Think about how many men she’s been with since their split in 1998!

Sources: Page Six, Pop SugarBillboard

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