Madonna came from humble beginnings, and her dedication and drive helped her rise to superstardom.

She is undoubtedly an icon whose career is the very definition of success.

But what of her love life?

Madonna performing on stage

Plus, constantly being in the spotlight cannot possibly be easy when it comes to dating.

Having had high-profile relationships for over 30 years, has Madonna finally found a love that will last?

She studied at the prestigious Alvin Ailey American Dance Theater but had aspirations to sing as well.

Split image of Madonna and Dan Gilroy

Gilroy encouraged Madonna to make her own music, which was a revelatory experience for her.

“That really clicked something off in my brain.”

You must return to America,'" she remembered.

Jean-Michel Basquiat close-up

“He really made me feel good.”

“I really felt loved.

Sometimes I’d write sad songs and he’d sit there and cry.

Madonna and Sean Penn smiling

Very sweet,” she shared.

Basquiat was a graffiti artist who rose to success in the early ’80s contemporary art scene.

I was blown away by that."

Madonna and Warren Beatty wearing sunglasses

But Basquiat’s substance use was a dealbreaker for Madonna.

Basquiat died at the of 27 due to a drug overdose, but his art lives on.

In 2017 Madonna took two of her children to see an exhibit featuring his paintings.

Vanilla Ice pointing at camera smiling

“My Past meets My Present!!

But the whirlwind romance was plagued by problems.

Penn had a reputation for losing his temper, especially with the paparazzi.

Tupac Shakur looking at camera

“His temperament is also similar to mine.

Madonna and Penn appeared together in 2016 at a charity benefitting Raising Malawi.

However, disagreements over fame and privacy eventually broke up their glamorous union.

Dennis Rodman holding mic on stage

Beatty also admitted to having had reservations about being included in the film himself.

“I said, ‘I don’t want to be in it.’

And she said, ‘Why would I want you in it?'”

Madonna and Carlos Leon at the Golden Globes

he shared with People.

But years later, Beatty had nothing but praise for his ex.

He also claimed that Madonna proposed to him at one point during their relationship and that freaked him out.

Madonna and Guy Ritchie

“Wait a minute, this is too fast …

I’m way too young for this,” the rapper recalled.

But it sounds like the couple had a good thing going while it lasted.

Madonna and Brahim Zaibat

And I hooked it up and I was very happy about it.”

However, the relationship was not built to last and its ending was somewhat surprising.

In 2017,TMZpublished portions of a letter Tupac had written to Madonna while incarcerated in 1995.

Timor Steffens posing

In it, he explained why he ended things with the singer, citing race as an issue.

The letter contained multiple apologies, with Tupac saying he never meant to hurt the pop star.

I was still having fun, still looking for new challenges.”

Madonna and Ahlamalik Williams posing

Personal trainer Carlos Leon caught Madonna’s eye as she jogged past him in Central Park one day.

The two went on to date and announced they would be starting a family together in 1995.

But everything went well, andLourdes “Lola” Maria Ciccone Leonwas born on October 14, 1996.

Madonna and Josh Popper

Madonna’s pal Rosie O’Donnell said of the pair, “It was a real relationship.

They made a valiant effort to stay together” (viaPeople).

I spoil her with love and American Apparel and Urban Outfitters."

“My head didn’t just turn, my head spun round on my body.

I was taken by his confidence.

He was sort of cocky but in a self-aware way,” Madonna said (viaPeople).

While the marriage lasted longer than Madonna’s former relationships, it had its fair share of issues.

In 2008, it was rumored that Madonna was having an affair with Yankees star Alex Rodriguez.

A rep for Madonna toldPeople, “Madonna and Alex have the same manager, Guy Oseary.

They know each other and Madonna took her kids to a Yankees game last week.

There’s really not anything to comment on beyond that.”

A source told People, “It was unraveling throughout the last year.

They were living separate lives and coming together every now and then for the cameras.”

Madonna and Ritchie divorced in 2008.

“She was just a woman almost like the others,” Brahim said.

“An exceptional artist and world-famous, of course, but a woman first.

I was just happy to meet her.

But not particularly stressed!”

But like everyone else, I know her hit songs."

The couple attended the Met Gala together in May 2013 but called it quits later that year.

I learn a lot."

And perhaps that’s why it ended as quickly as it did.

He and Madonna parted ways not long after that interview.

I’ve created a very unconventional family.

I have lovers who are three decades younger than me.

This makes people very uncomfortable."

While the couple seemed happy, they reportedly went their separate ways in April 2022.

And isn’t that what the Queen of Pop deserves?