Inside Madonna’s string of age-gap romances
Madonna’s newest 25-year-old toyboy is just the latest in a long line of flings she’s enjoyed with men up to 36 years her junior.
She was spotted getting cosy with her backup dancer – who is less than half her age – at a luxury Miami hotel last weekend.
But Ahlamalik Williams, 25, is just the latest in a long line of toyboys 61-year-old Queen of Pop, Madonna, has been linked to since her spilt from long-term partner Guy Ritchie, after which she decided she “wanted to have fun”.
Mum-of-six Madonna – who has been married twice but has dated a string of models, dancers and rappers – has been falling for increasingly younger men in recent years.
Her latest romances have seen enormous age gaps from 29 to 36 years – with professional dancer Ahlamalik only two years older than Madonna’s eldest child, 23-year-old Lourdes Leon.
In fact, it’s thought the Material Girl has only ever had one older boyfriend – now-82-year-old actor Warren Beatty, 21 years her senior, whom she described as “incredible” in bed.
Yet experts say Madonna’s penchant for toyboys isn’t surprising considering how youthful she is for her age – because younger lovers are fun, less demanding and can “keep up” with her.
Divorce coach Sara Davison tells Sun Online: “Madonna is super fit for her age – so most men her own age may struggle to keep up with that.
“If she wants good sex, fun and no strings attached then younger men are a great option.”
Relationship expert Sarah Louise Ryan adds: “When you are someone as successful as Madonna, it makes sense that she might opt to date in a way that seems much ‘lighter’.”
Here, experts and her biographer reveal the true reasons that she dated each of her toyboys.
The steamy kiss
Kevin Sampaio, 2017-2019
Age gap: 30 years
Before Ahlamalik, Madonna was linked to international model Kevin Sampaio.
At 31, Sampaio is 30 years the singer’s junior – but this age gap didn’t stop them striking up a romance in 2017 after the model appeared in the music video for Madonna’s single, Bitch I’m Madonna.
The pair even shared a steamy kiss in the footage.
Sampaio – who has worked for all of the big fashion houses including Dolce & Gabbana, Versace and Armani – is said to have kept his first date with Madonna a secret, with a source telling the Daily Mail the star liked how he didn’t “go running to the press”.
However, the couple’s romance is thought to have fizzled out at the start of this year.
No time for anything heavy
Timor Steffens, 2014
Age gap: 30 years
Madonna enjoyed another age gap relationship in 2014 with dancer Timor Steffens – then 30 years her junior, aged 26 – who has since admitted he has a penchant for older lovers himself.
But the couple’s romance wasn’t to last.
The then-56-year-old Hung Up star reportedly rowed with Steffens as the family celebrated her son Rocco’s 14th birthday in the south of France, and the pair split up.
A source told US Weekly at the time: “Madonna politely asked Timor to take his luggage and leave. He packed up and left the trip and said they were done.”
Madonna then moved on to party in Ibiza without Timor.
The source added: “It was never serious, and she was never that into it. She’s been working on her album and getting Lola off to school, no time for anything heavy.”
Major sexual chemistry
Brahim Zaibat, 2010-2013
Age gap: 29 years
Madonna dated French dancer Brahim Zaibat from 2010 to 2013, after the pair met when Zaibat, then 23, danced at the launch of the icon’s clothing line at Macy’s store in New York.
Despite their 29-year age gap, the pair had huge sexual chemistry.
“Although his English wasn’t fluent, and Madonna couldn’t speak French, their sexual chemistry soon swept such trifles aside,” biographer J. Randy Taraborrelli wrote last year.
Divorce coach Ms Davison tells us: “For many women it is a huge confidence boost to be found attractive by a younger man. It’s great for self esteem to rediscover your sex life and can reignite fires that went out years ago.”
According to pals, Zaibat and Madonna’s relationship was initially “problem-free”. In 2012, the dancer even performed alongside Madonna during the Super Bowl halftime show in the US.
But just a year later, the pair went their separate ways.
Fun and self-discovery
Jesus Luz, 2008-2010
Age gap: 29 years
Madonna met Brazilian model Jesus Luz on a cover shoot for W magazine in December 2008.
They began dating but just over 12 months later, in February 2010, it was reported that they had split up because of their age difference and “lack of common interests”.
“It was Luz who initiated the split,” a source told the Chicago Sun-Times at the time.
According to Ms Davison many relationships between women and much younger men, like Madonna and Jesus, are “not long lived as lifestyles are so different”.
“It’s not easy to integrate a much younger partner into every day life, especially if you have children,” she tells Sun Online. “So it’s more for fun and self discovery.”
Since the split, Jesus, now 32, has turned his hand to DJing and put his footwork to the test in 2013 as a contestant on Italy’s version of Strictly Come Dancing.
You Must Love Me
Alex Rodriguez, 2008
Age gap: 18 years
Before Jesus, Madonna had a fling with Alex Rodriguez – nicknamed A-Rod – with the pair spotted “looking close” at a New York City restaurant.
In November 2008, Rodriguez looked on proudly from the front row of the star’s concert in Florida, as she serenaded him with the ballad You Must Love Me.
Just months earlier, Madonna had responded to rumours of an affair with Rodriguez, denying she was behind the recent break-up of his marriage to wife Cynthia.
“I am not romantically involved in any way with Alex Rodriguez,” she said in a statement, adding that she had “nothing to do with the state of his marriage”.
Former baseball star Rodriguez, who turned 44 in July, is now engaged to actress Jennifer Lopez.
The strong life partner
Guy Ritchie, 2000-2008
Age gap: 10 years
Madonna’s marriage – and split – from famous film director Guy Ritchie in the 2000s may have been the catalyst for her love of increasingly young toyboys.
The superstar tied the knot with second husband Guy at a celeb-studded ceremony in the Scottish Highlands in 2000, when she was 42 and he was 32.
However, according to Mr Taraborrelli’s Madonna biography, one of Guy’s friends claimed the couple’s relationship was “one scene of emasculation after another”.
The pair, who have two children together, divorced in 2008.
And Mr Taraborrelli writes: “After the break-up, Madonna came to a decision. She no longer wanted a strong and equal partner in her life.
“Instead she wanted fun at the end of a stressful day, good sex and a few laughs – in short, a companion who’d make few demands of her. And he’d have to be young and hot.”
Ms Davison tells Sun Online: “Many women turn to much younger men after a break-up – I see this often in my coaching clinic. There are some real benefits to dating a much younger man when you have come out of a marriage and your confidence may have taken a knock.”
And Ms Ryan adds: “It seems like Madonna associates meeting someone older with baggage and also lacking of sense of fun and so the way she can enjoy escapism, at least in her mind, is to date someone who she deems to have a different, perhaps more youthful outlook on life.”
The personal trainer
Carlos Leon, 1994-1997
Age gap: Eight years
Madonna started dating personal trainer Carlos Leon – eight years her junior – after they met in New York City back in 1994, when she was in her 30s.
The pair were long-rumoured to be engaged, but called off their romance just months after welcoming daughter Lourdes in October 1996.
Although Madonna and Leon continue to co-parent Lourdes, she didn’t attend his wedding to designer Betina Holte in 2013.
Before Carlos, Madonna had been linked to a string of other younger lovers – including basketball star Dennis Rodman (three years younger), the late rapper Tupac (13 years younger), rapper Vanilla Ice (nine years younger) and the late lawyer John F Kennedy Jr (two years younger).
But her one older lover was the now-elderly Warren Beatty, with the pair striking up a 15-month relationship while they were filming Dick Tracy.
At the time, Beatty was 52 while Madge was just 31.
The ‘coolest guy in the universe’
Sean Penn, 1985-1989
Age gap: 2 years
Madonna’s first husband was also a toyboy – only just.
Madonna, then 27, tied the knot with Hollywood actor Sean Penn, 25, in August 1985, just six months after she first met him while filming the music video for Like A Virgin.
The couple’s romance played out in front of the world’s tabloids, with a loved-up Madonna dedicating her 1986 True Blue album to Penn, “the coolest guy in the universe”.
But there was trouble in paradise, with the pair’s 1986 film Shanghai Surprise flopping at the Box Office and Penn reportedly becoming jealous of Madonna’s male friends.
They had an “amicable” divorce in 1989, and have since supported each other’s careers.
In 1991, Madonna released the documentary, In Bed With Madonna, in which she was asked to name the love of her life. She coyly whispered back one single word: “Sean.”
The tragic lover
Jean-Michel Basquiat, 1982
Age gap: 2 years
Madonna, then an unknown aspiring singer, was working on her breakthrough debut album at the time of her short-lived relationship with artist Jean-Michel Basquiat.
At the time, he was 22 – two years younger than her.
But while Basquiat was a talented artist who dazzled pop art icon Andy Warhol and befriended stars like Debbie Harry and David Bowie, he struggled with demons.
Whenever his paintings sold – for up to $14,500 each, the cash went straight towards heroin.
Madonna would later recall: “He wouldn’t stop doing heroin.
“He was an amazing man and deeply talented — I loved him.”
Aged just 27, Basquiat was found dead of a heroin overdose in his Manhattan studio.
The back-up dancer
Ahlamalik Williams, current ‘lover’
Age gap: 36 years
If rumours about Madonna’s latest flame are true, Ahlamalik will be her youngest yet.
The backup dancer, who is 36 years Madonna’s junior, was spotted engaging in a PDA session with the pop legend on a hotel balcony in Miami last week.
At one point, he appeared to give her a shoulder massage.
Ahlamalik has been on tour with Madonna since 2015 – yet experts have warned that any passionate romance between the pair could be short-lived.
“Younger men are much more likely to be happy to fit in with Madonna’s lifestyle than impose their own rules on her,” says Ms Davison.
“While this can make it easier for Madonna, it may also get a bit boring to have someone extremely compliant around.
“But the relationships are fun while they last!”
This article originally appeared on The Sun and was reproduced with permission.
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