Cristiano Ronaldo: 15+ Love Stories From the Ballon d’Or Legend

Cristiano Ronaldo: 15+ Love Stories From the Ballon d’Or Legend

Cristiano Ronaldo has achieved a lot in his career as a professional soccer player. With his good looks, wealth, and solid career, it’s not surprising that many women find him attractive. He has had many romances and heartbreaks over the years, and in this article, we will explore some of the women who have caught his eye and left an impression on him. Ronaldo has become quite the heartthrob in the sports world.

Not So Rich, Not So Handsome

It’s not hard to picture Cristiano Ronaldo as poor and unattractive since that is actually what he was like during his childhood. He was born in one of the most deprived areas of Madeira and his family struggled just to make ends meet.


The sportsman shared a tiny room with his three siblings, as there was no extra space in their home. However, he was fortunate enough to have discovered his love for soccer from a young age, which eventually led him to great success and achievements in the sport.

What His Mother Was Hiding

If you observe Cristiano Ronaldo’s life on his social media channels, it’s likely that you’ve observed the strong bond he shares with his mother. Nevertheless, Mrs. Maria Dolores revealed something that startled the entire globe a couple of years ago.


The mother of the athlete confessed that she had planned to end her pregnancy upon learning that she was pregnant. This decision was made due to the financial instability of her family, as she was worried that adding a fourth child would only exacerbate their situation.

Young, But Talented

At the age of three, Cristiano Ronaldo had his initial interaction with a soccer ball. At the age of seven, he joined children’s clubs and demonstrated great potential, eventually becoming a standout player among his peers. By the time he was nine years old, both the Madeira Sports Club and National Sports Club expressed interest in recruiting him due to his remarkable abilities.

It was in that instance when both young Cristiano and his family comprehended that athletics was the route he should pursue.


A Diagnosis Almost Changes Everything

Despite being generally healthy, Cristiano received life-altering news at the age of 15. While undergoing routine medical examinations, it was discovered that the athlete had a heart condition that necessitated immediate surgery.

Upon discovering his health issue, they contacted his mother to obtain authorization for an urgent procedure. Luckily, with the use of a laser, the surgery was completed with minimal intrusion.

An Early Success?

It is evident that Cristiano Ronaldo experienced the beginning of success at a very young age. When he was just 17, he signed with Sporting Lisbon and played his first professional game against Inter Milan. His exceptional soccer ability quickly caught the attention of the media.


At the age of 17 in 2002, he was on the verge of being signed by Juventus thanks to a potential deal involving Marcelo Salas. But the plan fell apart since Salas refused to play for a Portuguese team.

Nothing Formal, Nothing

There have been no official claims that Cristiano Ronaldo had a formal relationship with Karina Ferro, a stunning Portuguese model. However, there are rumors that the two of them were romantically involved. Karina Ferro and Cristiano Ronaldo met when he was still relatively unknown.

According to reports, the brief romantic involvement between them took place in 2002. Despite Karina’s claim of being in a two-year relationship while Cristiano played for Sporting, it seems that it was nothing official or committed. Hence, they ended things and had an on-and-off association.


The First of Many

During his time at Sporting Lisbon, Cristiano was romantically interested in Jordana Jardel, who happens to be the sibling of his teammate, Mario Jardel. Jordana, who hailed from Brazil, was involved in modeling in Europe and was associated with Cristiano from 2002 to 2003.

The information available about the couple is limited, but it is clear that they had a pure and positive relationship. Jordana was the athlete’s inaugural girlfriend, and it is uncertain whether Cristiano had any previous romantic involvements.

The Debut That Catapulted Him

Sporting Lisbon and Manchester United had a friendly match in 2003, during which Cristiano Ronaldo’s outstanding performance drew the attention of the English team.


In a brief period, Cristiano’s coach quickly organized his transfer. As a result, he not only became the first Portuguese player on the Red Devils, but also the most costly transfer of a young player in the English team’s history. It was the start of CR7’s golden era.

The Flame Went Out

As soon as Cristiano moved to Manchester, his relationship with Jordana Jardel started to become distant. It was apparent that he had to spend the majority of his time in England rather than Portugal, which resulted in them being unable to meet as frequently as they used to.

The two individuals ended their relationship on good terms in 2003, handling the situation in a mature manner. They have even encountered each other at public events and treated each other with kindness and respect.


His Longest Lasting Love?”

The athlete held onto resentment towards Jordana for almost two years, and it wasn’t until 2005 that he was able to love again. Merche Romero, a Portuguese model and presenter, became the lucky woman who won his heart during an interview.

The courtship between Cristiano Ronaldo and his partner during his time at Manchester was going smoothly and lasting, as it was the longest relationship he had at the time. They stayed together and shared affection for nearly two years.

Nothing Lasts Forever

Regrettably, this association ceased in September 2006. During a candid interview, Merche admitted that the hectic timetables of both parties resulted in the difficult choice to part ways.


Romero confirmed that the separation was amicable and that he cherishes positive memories with Cristiano. Additionally, the model shared that Cristiano was one of her most satisfying sexual experiences.

A Cultural Mix

It’s believed that a Portuguese model who was residing in the United States stole the heart of a famous soccer player when he was just 23 years old in the year 2008. Her name is Mia Judaken, and she was only 18 years old at the time. Since then, Mia has become known for her low-key music career, where she blends together rhythms from Europe, Africa, and Latin America.

Perhaps that’s what intrigued Cristiano, but the reality was that there was not much information available regarding the potential connection between the two.


His Spark With Maria Sharapova

Cristiano and Maria crossed paths through their sports acquaintances and quickly formed a strong bond, which the media speculated might be a romantic connection.

Cristiano and Maria have been spotted together several times, but it’s unclear if they were romantically involved. Presently, they have a cordial relationship, and they haven’t addressed the rumors about their supposed love affair. Perhaps there was some truth to the rumors?

A Girlfriend From Bollywood

In 2006, Ronaldo terminated his relationship with Merche Romero and subsequently started a confirmed romantic relationship with Indian actress Bipasha Basu. They first met each other as presenters at a social event, and sparks of attraction ignited between them.


It is important to understand that the actress was in a relationship with another actor during that period. Nonetheless, there are reports claiming that she was seen kissing Cristiano at the event they attended together.

A Love Interest?

The media got very excited about the potential of Ronaldo being a part of a love scandal, but their enthusiasm quickly fizzled out when they realized the couple had only been together for a short period of time.

It is reported that the cause of the split was Bipasha Basu’s request to Cristiano Ronaldo for assistance with promoting her forthcoming film in theaters. It appears that the athlete declined to assist with the promotion, which angered the actress.


“Only Actresses Please”

It appears that Cristiano had become accustomed to swiftly changing partners, and his animosity towards the Indian girl was brief. Just a few weeks following the controversy with Bipasha, the athlete started a romantic relationship with a model and actress called Gemma Atkinson.

It’s odd that Cristiano Ronaldo’s love list only includes Gemma as the sole British woman, despite his many years playing for Manchester. Their relationship was short-lived, lasting only four months.

Getting a Taste of Latin Flavor

Cristiano had dated women from Europe and Asia for a few years, but then he sought love in Latin America where he met Mirella Grisales, a Colombian model whom he fell for when they coincidentally met on a red carpet event.


Similar to numerous other romances, this particular one persisted for a few months and concluded on a positive note. Mirella mentioned in an interview that the romance weakened due to distance, and it was the primary cause for their parting.

From Colombian to Spanish

In the beginning of 2008, Cristiano entered into a romantic relationship with Nereida Gallardo, a Spanish model, soon after breaking up with Mirella Grisales. They were frequently seen together, enjoying romantic dinners at fancy restaurants and nightspots.

The indications suggested that the couple was flourishing in love, but there were rumors that Nereida’s jealousy was causing difficulties in their relationship. Cristiano, however, remained tight-lipped about the topic.


Nereida Said It All

Regrettably, Cristiano and Nereida’s relationship came to an end within a few months, and ultimately their romance was nothing more than a summer fling, despite the fact that the breakup appeared to have a significant impact on the model.

While Ronaldo remained silent about their partnership, Nereida disclosed some information that was unverified. She claimed that the football player’s conduct was the primary cause of their breakup and accused him of being ill-mannered and conceited. Furthermore, she declared that she was the one who chose to end the relationship.

CR7 and Paris Hilton?

Back in 2009, there was a rumored romance between Cristiano Ronaldo and Paris Hilton. The two were seen together at a private party in the United States. At the time, Paris had recently ended a relationship while Cristiano had been single for a few months.


At the party, it was evident that Paris made romantic and suggestive advances towards Cristiano, to which the footballer responded in kind. However, this relationship was not short-lived.

Kim Was No Slouch

It appears that Paris confided in Kim Kardashian, her close companion, about Ronaldo. The sportsman and the influencer met at a gathering in Los Angeles, and it seems that he captured her interest right away.

Kim felt a powerful attraction for the footballer and decided to visit Madrid a few weeks later to spend some time getting to know him better. There were rumors that both of them were interested in starting a relationship, but the logistical challenge of distance and their busy schedules meant that they had to carefully consider their situation.


Kanye Changed the Landscape

Despite having a desire for love to arise, a new factor was introduced into the situation. This factor was none other than the rapper Kanye West. Kim began a relationship with the songwriter, leading her to leave behind her prior romance with Ronaldo.

The outcome of this story is familiar to us. In 2013, Kim and Kanye welcomed their first child and tied the knot in 2014 after years of being together. Cristiano was no longer involved in the situation.

A Short and Intense Love

Cristiano Ronaldo was rumored to have a brief love affair with Raffaella Fico, who is an Italian singer and model back in 2009. They were introduced to each other during a party and subsequently started a relationship to learn more about one another.


Raffaella was content with the romance, but neither of them was inclined towards a long-distance relationship. Hence, they mutually agreed to end the love affair in an amicable manner.

The Most Expensive Transfer

Ronaldo’s career took an unforeseen twist in 2009 when Manchester agreed to transfer him to Real Madrid for a staggering amount. The signing fee was so excessive that it became evident a few weeks later that it had made history as the most expensive transfer in the sport.

It is certain that all events occur for a reason, and at Real Madrid, Ronaldo’s athletic profession would be fortified even more. He would emerge as one of the top sportspeople globally.


Single Parent?

While achieving numerous sports accolades, Cristiano Ronaldo took a break to prioritize his family affairs. In the year 2010, the footballer surprisingly revealed the arrival of his first offspring, Cristiano Ronaldo Jr. This announcement caused a stir in both the sports and entertainment industries.

It appears that Ronaldo had a strong inclination to become a parent early on in his life, and in the absence of a reliable partner, he chose to pursue surrogacy as a means of having his first child. What is your opinion on this matter?

Why Surrogacy?

After the news broke out, it was evident that the public would require clarifications. Various assumptions surfaced, including speculations about the footballer’s sexual orientation. Nonetheless, during an interview, Cristiano declared that all he desired was to become a father, and he was open to the idea of doing so alone if necessary. He further added that if an opportunity presented itself, he saw no reason not to seize it.


Various psychologists and other professionals openly criticized the athlete’s behavior. Despite their opinions, he disregarded their comments and continued to relish his role as a father.

Irina’s Moment

Cristiano revealed his romantic involvement with Russian model Irina Shayk soon after their son was born. Although the details of their first encounter remain a mystery, their relationship proved to be one of the strongest in the global entertainment industry.

For some time, it was evident that both individuals were happy, and numerous media outlets speculated that a wedding could be in the near future. Additionally, the model had taken on a maternal role in the life of the athlete’s child.


Dolores’ Rejection

Despite the apparent strong affection between Irina and Cristiano, there was a strained relationship between the model and Cristiano’s mother, Mrs. Maria Dolores. This was because Maria was aware that Cristiano desired a big family, but Irina had no plans of becoming pregnant or having kids.

According to reports, the mentioned situation caused a rift in the relationship between Ronaldo’s mother and his wife. It is said that Irina was a source of disagreement between Ronaldo and his mother multiple times.

A Little Call to Andressa Urach

Cristiano Ronaldo engaged in one of the most audacious acts of unfaithfulness we have seen when he was in a relationship with Irina Shayk. He had the courage to contact Andressa Urach, a Brazilian model, immediately after she was crowned Miss Bum Bum, with the apparent objective of becoming acquainted with her.


Ronaldo was not expecting Andressa to disclose the truth during an interview a few months later, which Irina became aware of.

At Christmas Came the Break

Numerous people speculated that Cristiano Ronaldo and Irina were in a serious relationship, but during Christmas, their relationship deteriorated. It seems that the conflict arose because of Cristiano’s desire to spend the holiday with his mother, even though the couple was vacationing in Dubai.

This could have caused further tension between Irina and Cristiano’s mother, as after Christmas, Cristiano chose to spend New Year’s with his son alone, and Irina decided to leave.


An Abrupt End in Maldives

Irina Shayk was meant to celebrate her birthday with Cristiano in the Maldives on January 6, but due to their argument and subsequent breakup in Dubai, she ended up going alone without him.

According to certain sources, it was very saddening for her to have to celebrate her birthday all by herself in a distant country, which ultimately led to the end of the relationship.

“I Felt Ugly and Insecure…”

The bond between Cristiano Ronaldo and Irina Shayk completely fell apart in 2015. Despite never alluding to the issue, the football player was silent, while Irina spoke up a few months later in a globally shocking interview.


According to the model, it was very challenging to be in a relationship with Ronaldo, and she was cheated on multiple times. Irina eventually realized that Cristiano’s remarks and behavior made her feel unattractive and uncertain about herself.

Was Lucia His Consolation?

After breaking up with Irina Shayk in 2015, Cristiano was romantically associated with sports commentator, Lucia Villalon. The link between them began when Lucia shared a picture on her social media featuring the footballer. The photograph depicts both of them looking cheerful and displaying affection toward each other.

The press started to have doubts about whether she was the latest love interest of Ronaldo when they observed their affectionate behavior that could be perceived as romantic.


Denying the Obvious

Lucia was forced to provide statements about her rumored romantic involvement with Cristiano Ronaldo after weeks of speculation. According to the journalist, the relationship was a lovely friendship, and there were no intentions of anything further between them.

Naturally, the media was skeptical of this story and speculation persisted regarding the supposed romantic involvement. Regrettably, there was no way to substantiate it, and Ronaldo remained silent on the matter.

The King of the Ballon d’Or

Despite his unsuccessful romantic life, Cristiano Ronaldo’s career as a professional athlete was thriving. He had gained recognition as the top performer in the European League while playing for Real Madrid and had earned numerous Ballon d’Or awards due to his exceptional talent.


At this point Cristiano was already being compared to great soccer legends, such as Pele and Maradona. Of course, he has also been confronted by the media with his eternal “opponent”: Lionel Messi.

The Affair With Alessia Tedeschi

After the short scandal he starred in with Lucia Villalon, Cristiano was linked to Italian model Alessia Tadeschi. The two were spotted together in Italy on different occasions and it was more than obvious that between them there was more than just a friendship.

Once again the footballer’s statements were completely absent. However, Alessia herself confirmed that she had a short affair with him. Once again, the distance and the difference in agendas was what made the romance did not continue.


Miss Spain, Welcome

Cristiano Ronaldo has been with all kinds of models, but there are no misses in his list of loves, with the exception of Desiré Cordero. She was Miss Spain in 2014 and various magazines began to say that Cristiano already had a solid relationship with her. It seems that this was not so true.

They would have been together a few months, but Cristiano did not end up closing, because he did not trust her. There are even those who say that so much secrecy is because they signed a pact of silence.

Georgina Is Here to Stay

And everything seems to indicate that in 2016 Cristiano really found love. That year he met Georgina Rodriguez, an Argentine-born model and dancer who stole his heart at a party. Cristiano was so impressed with her that he had to arrange everything to see her again “casually.”


Little by little the relationship took shape, and they became one of the most solid couples in the sporting world. After all, who could resist Cristiano Ronaldo?

Eva and Mateo’s Welcome

It seems that Cristiano’s mother was right, and the sportsman’s intention is to have a rather large family. In 2017, having been in a relationship with Georgina for more than a year, he unveiled the birth of his twins, Eva and Mateo, both born in June of that year.

Once again the press was shocked, not only by the news that the athlete had returned to procreate, but also because, still having a partner, he had resorted again to the surrogacy method.


The Stork Returned in a Hurry

To confuse the public even more, in November of that year the couple unveiled the birth of their new baby girl. This baby girl was conceived in the regular way by Cristiano and Georgina. One way or another, this new birth cleared up some doubts.

Everything seems to indicate that the soccer player had already scheduled the surrogacy process before starting the relationship with the Argentinean model. Of course, he didn’t want to cancel it and while he was in the sweet wait, Georgina also got pregnant.

Farewell Real Madrid!

In 2018 Cristiano confirmed that he is a man of challenges. The player was negotiating a new contract with Real Madrid, however, he suddenly received an offer from Juventus and, without much thought, decided to leave with the Italian team.


According to the athlete he needed a challenge in his life, and for this it was necessary to leave Real Madrid. Few people expected such a radical change, however, the signed contract only had a duration of four years.

Undeniable Jealousy

While it is true that Cristiano and Georgina squander love whenever they are seen in public, it is also true that on more than one occasion the model’s jealousy has come to the fore at social events.

It is well known that Georgina does not like other women approaching Ronaldo while she is around. The Argentine has been photographed on several occasions grimacing in annoyance while Cristiano attends to his fans or takes a picture with a woman.


Back to His Origins

In 2021 Cristiano made public his intention to leave Juventus, it seems that in three years he had enough challenges. Immediately the club put him up for sale and the offers started coming in.

After a long list of proposals in August it was made public that Manchester had reached an agreement with Juventus to re-sign Cristiano Ronaldo. This contract would be for two years plus an optional one, and it was requested that Cristiano would continue to wear the iconic number seven.

Another Token of Love?

Yes, everything seems to indicate that Cristiano Ronaldo can’t get enough of enlarging his family. Recently the athlete and his partner announced through their social networks that they will become parents again. This time they will have twins in their lives.


There is still no information about the method they used for the gestation, but everything seems to indicate that again Georgina will be in charge of bringing the babies into the world. Both Cristiano and she have shown themselves happy through their Instagram accounts.

Where Is Cristiano?

To invent rumors, social networks and magazines are made. But it is also true that there are certain events in which it is impossible not to overthink. This is one: Alana Martina, daughter of Cristiano and Georgina, turned four years old and celebrated in the company of her siblings, her mom … but not her dad.

The party was big, with food and guests, but without CR7. This drew attention, because, although Cristiano was summoned by the Portuguese national team, some say that the party could be postponed.


Looking Pregnant

Between those rumors that Cristiano has not been present, Georgina has not stopped and already begins to show off her pregnancy. Twins are already coming and the sweet wait is going by faster and faster. It is also true that this is her first public pregnancy and, therefore, all the cameras are after her.

Cristiano Ronaldo has said several times how excited he is for two children to come, but between the move to the UK and national team call-ups, he hasn’t had time to spare.

Jealous at This Point?

Georgina Rodriguez is a woman of weapons to take, no matter if you have to take those weapons in the middle of the red carpet. So she did when she went along with Cristiano to the MTV EMA 2019, where there was also Rita Pereira, a well-known Portuguese actress to whom some claimed a relationship with CR7 in 2012.


In the scene, Georgina could be seen annoyed, showing some photos to Cristiano and looking sideways at Rita. All this only corroborates that CR7 and Rita were indeed more than friends.

Natacha Speaks Loudly

It is also true that the rumors of a breakup or conflict between Cristiano Ronaldo and Georgina Rodriguez have increased following Natacha Rodriguez’s statements. She is a voluptuous Portuguese model who told, in great detail, how she would have written Cristiano on Instagram, he would have replied and they would have spent a night together.

The serious part of all this is that this would have happened while Cristiano was already Georgina’s boyfriend, so he had asked her to keep the secret. Is it possible?


Red Hearts Make It Clear

The truth is that no one pays much attention to rumors of extramarital affairs, not even Georgina. Although they have not been seen so close, there is nothing conclusive that allows us to think that they are separated. In fact, many breathed a sigh of relief because Georgina has responded to Cristiano’s Instagram stories with lots of red hearts. Is it a sign of love?

Let’s hope those hearts continue with lots of life, especially for the two upcoming children and the four already present in the family.

Will There Be Only Six?

Believe it or not, with the arrival of the new twins the number of Cristiano Ronaldo’s children rises to six. Currently the press is wondering if the footballer hopes to continue enlarging his family or if six children will be enough for him.


The important thing is that we can notice all the love that both Cristiano and Georgina give to their children. We are definitely in front of a happy and very solid family. This can be noticed in every appearance they make.

Celebrity relationships often end before we even realize they began in the first place. However, it helps when some celebrities keep their relationships within the same field, or even within the same friend group.

Kate Hudson – Alex Rodriguez – Cameron Diaz

In 2010, some of Hollywood’s biggest names — actresses Kate Hudson and Cameron Diaz — were caught up in a love triangle with Yankee Shortstop, A-Rod. Hudson and A-Rod started dating between May and December 2009 where she was a regular visitor at Yankee Stadium. However, in May 2010, Diaz had been spotted leaving A-Rod’s NY penthouse.


Kiefer Sutherland – Julia Roberts – Jason Patric

This dramatic love triangle is something that would make the perfect rom-com! Actors Julia Roberts and Kiefer Sutherland met on the set of the movie Flatliners in 1990, and were due to marry at a ceremony in 1991 at one of the 20th Century soundstages.

However, just two days before her wedding, Roberts flew to Ireland with one of Sutherland’s closest friends. Roberts spent what was supposed to be her wedding day eating turkey burgers with Patric. After they flew home, the two become a couple, however, they eventually split in 1992.

Gwenyth Paltrow – Luke Wilson – Drew Barrymore

After filming Home Fries together — a movie centered around a wife getting revenge on her husband’s extramarital affair — stars Luke Wilson and Drew Barrymore dated for two years. They broke up shortly before they starred in Charlie’s Angels together, where Barrymore even wrote him as Cameron Diaz’s love interest.


After Barrymore and Wilson broke up, Wilson emerged with his new girlfriend, Gwenyth Paltrow, in July 2001. The pair had acted together in Wed Anderson’s The Royal Tenenbaums. The relationship only lasted a year before the pair broke up in 2002.

Sarah Silverman – Michael Sheen – Kate Beckinsale

Welsh actor, Michael Sheen, met fellow actress Kate Beckinsale when they starred in a production of The Seagull in 1995. Shortly after, the couple got together and had a daughter named Lily in 1999. However, after seven years together, the couple split in 2002 and Sheen had to return home from the US.

In 2014, Sheen found love again in comedian and fellow actress Sarah Silverman. Silverman often gushed about how much she loved Sheen saying that “I don’t think I ever really knew what love was.” However, it wasn’t meant to be and the pair split in 2018 after four years due to long distance.


Dianna Agron – Alex Pettyfer – Emma Roberts

After filming the movie Wild Child together, Emma Roberts and Alex Pettyfer took their on-screen romance into the real world in 2007. He was obviously quite smitten as Pettyfer has a tattoo of Robert’s initials inside a heart on his wrist. The two split in 2008.

After gaining attention from the television show, Glee, Dianna Agron found her new beau, Pettyfer, when they acted alongside each other in the thriller I Am Number Four. After less than a year of dating, and despite living together, the two split in 2012.

Demi Lovato – Joe Jonas – Gigi Hadid

The world came to a standstill when long-time friends, Joe Jonas and Demi Lovato, decided to give their relationship a go in 2010, three years after they first met on the set of Camp Rock. However, it wasn’t meant to be and the pair broke up just after a few months of dating.


Fast forward through a few years of other relationships and before long, Jonas landed model Gigi Hadid after they met through mutual friends. During their six-month relationship in 2015, they spent a lot of time with friends in the spotlight. The pair broke up in November 2015.

Nikki Reed – Ian Somerhalder – Nina Dobrev

After meeting on the set of The Vampire Diaries, costars Nina Dobrev and Ian Somerhalder enjoyed a three-year-long relationship together. They first went public in 2010, before ending things in 2013. The two remained close and kept things professional while they worked on TVD.

In 2014, Ian Somerhalder sparked up a romance with Twilight actress Nikki Reed. After six months of dating, Ian popped the question and the pair were married in April 2015. The couple has one daughter together, Bodhi Soleil, who was born in 2017. They remain good friends with Dobrev.


Denise Richards – Richie Sambora – Heather Locklear

After divorcing Mötley Crüe drummer Tommy Lee, actress Heather Lockler fell in love with Bon Jovi lead guitarist Richie Sambora. Quickly after meeting, the pair were married in 1994 and had their daughter, Ava Sambora, in 1997.

After 11 years of marriage, Locklear and Sambora split. However, Sambora started dating Denise Richards, who was going through her own divorce with ex-husband Charlie Sheen. This came as a shock to Locklear as both couples had been friendly throughout their relationships!

Cameron Diaz – Sean Combs – Jennifer Lopez

From 1999 to 2001, the biggest celebrity couple was JLo and Puff Daddy, known today as Sean Love Combs. The pair started their relationship in 1999 and made a number of public appearances including the Grammy Awards in 2000 when JLo wore that iconic Versace gown.


However, it was revealed that infidelity was the reason for this breakup. Years later after JLo moved on, P Diddy dated Cameron Diaz on and off for four years, from 2008 to 2012. Diddy reportedly said that “if I could turn back time, things would be different.”

Lindsay Lohan – Aaron Carter – Hilary Duff

Some celebrities wish they had a feud as iconic as this one! It all started when Hilary Duff started dating Aaron Carter in 2001 after meeting on the set of Lizzie McGuire. Carter admitted to “getting bored” of his year-long relationship with Duff and decided to start dating Lindsay Lohan.

However, Lohan and Carter only dated for a few months before he was caught cheating on her with someone else. Despite this, the feud between Duff and Lohan intensified, which included gatecrashing each other’s movie premieres. Talk about catty!


Kristen Stewart – Robert Pattinson – FKA Twigs

R Patz and Kristen Stewart drove fans wild when it was found out that their on-screen relationship in Twilight was, in fact, real. The couple got together in 2008 but it ended abruptly when it was announced that Stewart cheated on Pattinson with director Rupert Sanders in 2012.

After dealing with his heartbreak, Pattinson later found love with British singer, FKA Twigs in 2014. They later got engaged in 2015, however, hectic travel schedules eventually caused their split in 2017. Twigs later wrote the song “Cellophane” about the end of her relationship.

Drew Barrymore – Fabrizio Moretti – Kristen Wiig

Drew and Kristen are examples of how to be friends when they date your ex. The Strokes drummer Fabrizio Moretti started dating Drew Barrymore after they met at The Strokes concert in 2002. After five years of dating, they went their separate ways in 2007.


Fast forward to 2012 and Moretti is dating Saturday Night Live star — and Barrymore’s Whip It! co-star — Kristen Wiig. Barrymore stated that the relationship ‘wacky.’ Just 18 months later, the pair called it quits, although it was an amicable breakup.

Lance Armstrong – Sheryl Crow – Owen Wilson

Lance Armstrong and Owen Wilson seem to have the same taste in women, as they share not one, but two exes! The first is Sheryl Crow, who dated Wilson after starring in The Minus Man together. They dated from 1999 to 2001, even attending the Vanity Fair Oscars party together in 2000.

After Wilson, Crow started a relationship with athlete Lance Armstrong in 2003. Their love flourished and the pair were engaged by 2005. However, when Crow suggested having children soon after Armstrong’s first marriage, this ended the relationship in 2006.


Taylor Swift – John Mayer – Katy Perry

Don’t you think 19 was too young to be messed with, John? A love triangle that set the wheels in motion for Swift and Perry’s feud, Taylor Swift dated John Mayer for two months when she was 19 and he was 32. Her heartbreak inspired the ballad, “Dear John,” on her third album, Speak Now.

Katy Perry entered an on-and-off-again relationship with Mayer in 2012, before officially calling things off in February 2014. Never fear, the Perry and Swift feud has ended, with Swift sending Perry a handstitched blanket for her newborn daughter, Daisy, in 2020.

Jennifer Aniston – Adam Duritz – Courteney Cox

Yes, Friends co-stars Jennifer Aniston and Courteney Cox actually share an ex-boyfriend. Aniston met Counting Crows frontman Adam Duritz through mutual friends and eventually began dating in 1995. Unfortunately, not much information is known about why the two broke up.


Two years later, and three years after Friends started, Courteney Cox began seeing Duritz after appearing in the music video for “A Long December.” Again, it isn’t known why the pair broke up, but Cox eventually married fellow actor David Arquette in 1999.

Miley Cyrus – Nick Jonas – Selena Gomez

The most important love triangle to exist for ’90s kids. Disney Channel stars Cyrus and Jonas became boyfriend and girlfriend the day they met backstage at a concert in 2006. The pair were in love with each other until 2008 when they eventually ended things. Cyrus wrote the song “7 Things” about Jonas.

Shortly after their breakup, Jonas proceeded to date fellow Disney star Selena Gomez. It was reported that Gomez was in love with him. However, this sparked a feud between Gomez and Cyrus, which has since been resolved. Were you #TeamMiley or #TeamSelena?


Kylie Jenner – Cody Simpson – Gigi Hadid

Before Tyga and Travis Scott, Kylie Jenner dated Australian singer Cody Simpson in 2011 — her first official relationship. Whilst it’s not known how long they dated for, it clearly didn’t end well with Simpson saying that “the whole K-O-D-Y thing didn’t really work for me.” Yikes!

After the dust had settled, Simpson sparked up a relationship with model Gigi Hadid in 2013. The pair were often spotted on Instagram and red carpets together, dating on-and-off for two years before ending things in 2015. Simpson said that he loved his ex, but wanted to remain focused on his music.

Liam Hemsworth – Miley Cyrus – Kaitlynn Carter

A will-they-won’t-they relationship we’re sure everyone remembers! Cyrus met Australian actor Liam Hemsworth in 2019 on the set of their movie The Last Song. The couple dated on and off until their engagement in 2012, but that was called off in 2013. However, by 2016, the pair were back together and married in 2018, before splitting once more in 2019.


After her breakup with Hemsworth, Cyrus started dating actress Kaitlynn Carter, who had also just separated from her husband. After just two months, the pair decided that they’re better off as friends and ended their romance.

Olivia Rodrigo – Joshua Bassett – Sabrina Carpenter

The love triangle currently taking TikTok by storm! Stars of the Disney+ show — High School Musical: The Musical: The Series — Olivia Rodrigo and Joshua Bassett apparently were more than friends off-screen. However, after Rodrigo posted a TikTok about failed relationships in August 2020, it seemed to be over.

Not long after, Bassett was spotted with fellow rising star Sabrina Carpenter. Dating rumors were fuelled after the pair were spotted at lunch together where they were making TikToks. Rodrigo dropped her single “Driver’s License” in January 2021, which seems to be inspired by her recent heartbreak. Ouch.


Big Sean – Ariana Grande – Pete Davidson

In “Thank U, Next,” Ariana Grande named a number of exes — two of whom are rapper Big Sean and SNL comedian Pete Davidson. Grande briefly dated Big Sean in 2014, going public in 2015 at the Grammys. It wasn’t long until the couple broke up due to their touring schedules, which would have kept them apart for a year.

In 2018, Ariana Grande and Pete Davidson experienced a whirlwind romance. In May, they began dating after they first met in March 2016. In June, Grande confirmed she and Davidson had gotten engaged. However, by October, the two had called off their engagement and ended their relationship.

Selena Gomez – The Weeknd – Bella Hadid

Bella Hadid and The Weeknd are truly the ultimate on-again, off-again couple. Reports of their romance first surfaced in 2015, when they were spotted at Coachella together. In 2016, it was reported the couple had split due to busy schedules.


However, two months later in January 2017, The Weeknd was spotted kissing Selena Gomez in Santa Monica. The couple spent 10 months together, even attending the 2017 Met Gala ball as a couple. After their breakup in October 2017, though, The Weeknd and Hadid quickly reunited and became official in April 2018.

Camille Rowe – Harry Styles – Kendall Jenner

Music’s most eligible bachelor Harry Styles has found himself in a string of high-profile relationships over the years. After ending his relationship with Taylor Swift in early 2013, the former One Direction star was spotted with Kendall Jenner later that year, before committing to a year-long relationship in 2016.

Styles then found love with Victoria’s Secret model Camille Rowe. They began a year-long relationship after first being spotted at a Fleetwood Mac concert in NYC. The couple split in mid-2018, and the breakup inspired many of the songs on Styles’ album, Fine Line.


Selena Gomez – Justin Bieber – Hailey Baldwin

Gomez and Bieber stepped out as a couple for the first time in 2011. From then on, it was a hectic on-again, off-again romance — breaking up in 2012, before making up briefly for three months in 2014. They reconnected in late 2017 but ended things in early 2018.

Bieber and Baldwin first met at a fan event when Baldwin was just 12 years old. After a flurry of family vacations together, they first got together in 2016, however, the fling fizzled out by November of that year. After Bieber ended things with Gomez in 2018, he and Baldwin rekindled their love and were engaged by May 2018. They got married three months later.

Nikki Reed – Ryan Phillippe – Ashley Greene

Imagine both of your exes being former Twilight stars? Well, that’s the case for Ryan Phillippe! In 2007, rumors flew after Nikki Reed and Ryan Phillippe were spotted in Hollywood’s hotspot, Winston’s, shortly after his split from ex-wife, Reese Witherspoon. Reed was just 18 at the time.


In March 2013, Phillippe and Ashley Greene were spotted leaving LA’s Vignette Lounge together. No other details seemed to emerge about the couple, and it’s likely that it was only just a case of wrong place, wrong time. Still, no drama ever came between the two costars!

Taylor Swift – Jake Gyllenhaal – Reece Witherspoon

The exes were keen to move on after their divorce. After splitting from Ryan Phillippe, Reese Witherspoon was spotted with fellow actor Jake Gyllenhaal in 2007. They eventually broke up after two years. Since then, Gyllenhaal has praised his ex, calling her “one of the smartest, strongest people I’ve ever met.”

Gyllenhaal was then spotted with Taylor Swift multiple times in late 2010. However, Swift and Gyllenhaal broke up in January 2011, reportedly by text. Swift, inspired by her breakup from Gyllenhaal, wrote “All Too Well” and “State of Grace” for her fourth album, Red.


Josh Hutcherson – Zoey Deutch – Avan Jogia

In 2012, Hunger Games actor, Josh Hutcherson, is spotted flying from Vancouver to LA with suspected girlfriend Zoey Deutch. Not much is known about their relationship, but what is known is that Hutcherson was friends with Deutch’s future boyfriend, Avan Jogia.

Deutch and Jogia met in 2012 before coming out as an official couple at the Kid’s Choice Awards. The pair was notoriously quiet about their relationship, only posting on Instagram once every so often. They split amicably in 2017, but have appeared alongside each other in Year of Spectacular Men and Zombieland 2.

Jamie Campbell Bower – Lily Collins – Taylor Lautner

After filming the movie, Abduction, in 2010, Lily Collins and Taylor Lautner decided to give their relationship a go. Lautner even revealed that the pair “had hit it off right away.” However, it didn’t last long with the pair splitting just one week before their film premiered.


Finding love again, this time on the set of The Mortal Instruments: City of Bones in July 2o12, Collins got together with costar Jamie Campbell Bower. The couple was together from 2012 to August 2013, before trying again two years later in 2015. Unfortunately, it didn’t work and they broke up for good later that year.

Owen Wilson – Kate Hudson – Lance Armstrong

Surprise! Another celebrity love triangle featuring Owen Wilson and Lance Armstrong as exes. This time, the special lady is none other than Kate Hudson. Wilson and Hudson first started dating after meeting on the set of You, Me and Dupree in 2006. They split up in 2007 before trying twice more in 2008 and 2009.

Shortly after her second try with Wilson, Hudson found herself in a short three-month whirlwind romance with Lance Armstrong. The pair was said to have met while they were both on vacation in the Bahamas in May 2008.


Perrie Edwards – Zayn Malik – Gigi Hadid

Shortly after becoming part of the biggest boyband of all time, Zayn Malik met Little Mix member Perrie Edwards backstage on The X Factor in 2011. Zayn even got a cartoon of Perrie tattooed on his arm prior to his engagement. Five months after Zayn left One Direction, he ended things with Perrie.

Two months later, Malik was spotted with Gigi Hadid and in January 2016, she was the main star in his music video for “Pillowtalk.” In March 2018, they confirmed their breakup on social media, but that didn’t last long. In September 2020, the pair announced the birth of their first child.

Drake – Rihanna – A$AP Rocky

Rihanna first met her future beau, Drake, in 2005 at a restaurant in Toronto. However, it was still another four years until the two finally went on their first date. For years, the pair never disclosed whether or not they were in a relationship, but it was hinted in Drake’s 2016 VMA speech for Ri Ri’s Vanguard Award.


Rihanna and A$AP Rocky have been friends for years, but there’s reason to believe that there’s now a budding relationship. After Ri Riri broke up with her long-term boyfriend in January 2020, rumors began flying that the two have become more than friends. They even spent Christmas in Barbados!

Kylie Jenner – Tyga – Blac Chyna

Blac Chyna first met rapper Tyga in 2011 when she was featured in a music video for “Rack City.” In October 2012, Chyna gave birth to the couple’s first and only child, King Cairo, and Tyga proposed a month later. The pair ended their relationship in 2014.

Two months after the split, Tyga was seen in matching Halloween costumes with long-time friend Kylie Jenner. In 2015, the pair confirmed their relationship but they split right before the 2016 Met Gala. They got together for a short time in 2017, before breaking up for good in April.


Joey King – Jacob Eldori – Zendaya

Joey King and Jacob Eldori first met each other when filming Netflix hit The Kissing Booth in 2017. About one month into shooting, the pair decide to try a romantic relationship. While the couple split quietly in November 2018, they have since worked together in The Kissing Booth 2.

Eldori met his rumored girlfriend, Zendaya, on set the hit television show, Euphoria. The pair were spotted on holiday and several times in New York City for many fashion events. However, after long-distance due to quarantine, things reportedly didn’t work out between the two.

Pete Davidson – Kaia Gerber – Jacob Eldori

Pete Davidson started dating Kaia Gerber in 2019 after the pair reportedly met backstage at an Alexander Wang fashion show. The couple spent a lot of 2019 together, however, they broke up at the beginning of 2020 as Pete wanted to focus on making his mental health a priority.


Cue September 2020, when Gerber was spotted leaving Nobu in Malibu with Jacob Eldori. After falling for each other in quarantine, Eldori and Gerber officially announced that they’re dating with matching outfits and Instagram posts. We hope that it lasts!

January Jones – Jason Sudeikis – Olivia Wilde

Pete Davidson isn’t the only SNL cast member to land himself in high profile relationships! Soon after separating from his first wife, Kay Cannon, Jason Sudeikis pursued a six-month relationship with actress, January Jones. They split in January 2011.

In November 2011, Sudeikis met actress-turned-director Olivia Wilde. After becoming engaged in January 2013, the pair never set a wedding date, but did have two children together. In November 2020, they announced they had split at the beginning of 2020. Wilde has since been linked to Don’t Worry Darling costar Harry Styles.


Lenny Kravitz – Lisa Bonet – Jason Momoa

Lenny Kravitz and Jason Momoa are perfect examples of how to stay friends with your exes. Kravitz eloped with actress Lisa Bonet in 1987. However, the couple eventually divorced in 1993 and spent the following years co-parenting their daughter, Zoë Kravitz.

In 2013, Momoa met Bonet — his childhood crush — at a jazz club. They soon began to date, and eventually tied the knot in 2017. The couple has two children together, Lola Iolani and Nakoa-Wolf. Kravitz and Momoa sparked a great friendship, with Kravitz stating that he “immediately felt love” for Momoa.

Kieran Culkin – Emma Stone – Andrew Garfield

Actress Emma Stone hasn’t had many high-profile relationships, but both of her exes are fellow actors! Stone met her first beau, Kieran Culkin, on the set of Paper Man. As Stone was not yet famous, her relationship and eventual breakup with Kieran in 2011 went under the radar.


After meeting on the set of The Amazing Spider-Man in 2010, Stone started a long-term relationship with Andrew Garfield. The pair remained private about their relationship to ‘preserve’ it, however, scheduling issues in 2015 eventually brought their relationship to an end. Despite splitting, the two are still good friends.

Kate Moss – Jamie Dornan – Kiera Knightley

Mr. Grey has a string of famous exes! When Kiera Knightley was starring in films such as Love Actually and Pirates of the Caribbean, Jamie Dornan was by her side. The two dated each other from 2003 to 2005 after they met on an Asprey photoshoot.

Despite being branded the ‘Male Kate Moss’ by British GQ, it is rumored that Dornan dated the famous supermodel at one point after his relationship with Knightley ended. The pair apparently got close in 2006 after appearing in a Calvin Klein advertisement together.


Jenny Slate – Chris Evans – Jessica Biel

It’s hard to imagine how Marvel hunk Chris Evans is still single, however, he has linked up with some famous leading ladies. In 2001, Evans first got together with fellow actress Jessica Biel and they stayed together for five years. The couple split in 2005 despite rumors of the pair getting married.

Fast forward to 2016 with Evans entering his second-longest relationship with Big Mouth actress Jenny Slate after they met on the set of their movie, Gifted in 2015. They split in early 2017 but were reportedly back on by late 2017. They eventually split in March 2018, although they remain good friends.

Calvin Harris – Taylor Swift – Tom Hiddleston

This is the most intense love triangle to make the list. Taylor Swift famously dated Scottish DJ Calvin Harris from 2015 to 2016. They remained relatively private, only posting on social media every now and again to confirm they’re still together. In June 2016, they announced their split on social media.


Two weeks later, Taylor was spotted kissing Tom Hiddleston near Swift’s Rhode Island home. Harris was fuming and unfollowed Swift, as well as her family, on Instagram. After a summer romance in 2016, Hiddleswift was no more due to publicity issues. We wonder where Tom’s “I <3 T.S.” shirt is?

Angelina Jolie – Brad Pitt – Jennifer Aniston

It wouldn’t be a celebrity love triangle if we didn’t mention the most iconic triangle of the last three decades! Jennifer and Brad first met each other in 1994, but didn’t go on their first date until 1998 when their agents set it up. By 1999, the pair were engaged!

However, once Pitt met Jolie on the set of Mr. & Mrs. Smith, Jen and Brad announced their separation. After spending the better part of a decade together, Pitt and Jolie officially tied the knot in 2014. However, in 2016, they officially announced their divorce.


Britney Spears – Justin Timberlake – Cameron Diaz

Another iconic 2000s love triangle! After meeting for the first time on The Mickey Mouse Club, Britney Spears and Justin Timberlake entered a three-year-long relationship (1999 to 2002). They even wore matching outfits, does anyone remember the double-denim outfits at the AMA’s?

However, a year later in 2003, Timberlake found love with Cameron Diaz after the pair had met at the Nickelodeon Kids Choice Awards. The pair dated on and off over four years before eventually splitting in 2007. Timberlake and Diaz have managed to keep things professional and have worked together in 2011 for Bad Teacher.

Jamie Foxx – Katie Holmes – Tom Cruise

After the iconic Oprah Winfrey Show interview in 2005, we all knew how Tom Cruise felt about Katie Holmes a month into dating. Their whirlwind romance saw the pair engaged after three months of dating, and married in 2006 shortly after the birth of their daughter, Suri.


A year after her divorce from Cruise, in 2013, Holmes was spotted with Jamie Foxx for the first time. The two remained private about their relationship, only making one official appearance together at the 2019 Met Gala. However, shortly after the Gala, Holmes and Foxx called quits on their six-year fling.

Nick Cannon – Kim Kardashian – Nick Lachey

In a world after her split from Ray J, and while she was still working as Paris Hilton’s assistant, Kim Kardashian dated actor and singer Nick Lachey. However, in 2019, Lachey spilled the tea and admitted they only ever went on one date to watch The Da Vinci Code.

In September 2006, Kardashian and Cannon began their relationship. It wasn’t long before things came crashing down in January 2007 after accusations of mistrust and lying were thrown around. They split just before Kim found fame on her family’s reality show, Keeping Up With the Kardashians.


Selena Gomez – Taylor Lautner – Taylor Swift

Real friends share exes! In 2009, Selena Gomez started dating actor Taylor Lautner after they both met in Vancouver shooting their movies. Gomez starred in Ramona and Beezus and Lautner starred in Twilight: New Moon. The pair broke up after Lautner wanted to stay single for his career.

His head was turned, however, when he met singer-songwriter Taylor Swift. They met on the set of the movie Valentine’s Day and dated briefly from August to December 2009. It is rumored that Swift’s song, “Back to December,” is about Lautner, where she mentions his tan skin and sweet smile.

Kourtney Kardashian – Scott Disick – Sofia Richie

Kourtney Kardashian and Scott Disick were a couple long before Keeping Up With the Kardashians aired. The pair met in Mexico in 2006 and welcomed three children together in their tumultuous 10-year-long relationship. They officially split in 2015 after Scott was spotted getting cozy with one of his exes.


In 2017, Disick debuted his relationship with 19-year-old model, Sofia Richie, daughter of Lionel Richie. Their relationship was very serious, and Richie even met Disick’s three kids along with Kourtney. Despite how serious the pair were, they split after three years in 2020.

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