Drake wanted Rhianna nobody had a chance. So now he dumps her on social media. He is hurt.

Drake isn’t just one of the highest-earning artists in the music industry, but he is one of the most popular as well. When we say popular, we’re not only talking about his music but his romantic endeavors as well.

With status as big as Drake’s it’s strange that we don’t have more information about his love interests. But, for now, we’ll give you what we do know including the women’s names and when they may have been involved.

Putting a Face to the Name

Drake’s hit single “In My Feelings” has had millions of downloads since its release in 2018. However, people all around the world have been dying to know who “Kiki” was and if she loved him! If you were one of these people, then fear not because we have the answer.

Her name is Keshia Chante and dated Drake for some time in the 2000s. Not only was she his first love, but they’ve been able to remain friends despite their split. During an episode of 106 & Park Drake admitted to Chante that he “actually rapped about you before.” During his references to puppy love in “Fallen” and “Deceiving,” he’s talking about her. Not only does she hold this title but she has also gone on to become a successful singer and television personality.

Dating Him Was Too Overwhelming

What do you classify as having dated someone? For us, it’s having gone on even one date with the person, which is why Kat Dennings is on this list. For those who don’t know, Dennings is an extremely talented actress, known for her role in 2 Broke Girls. In 2005, Drake and Dennings gave in to their chemistry and went on a date.

However, that was as far as it went. According to Dennings, it was all simply too much. After having seen him just once, she was bombarded with hate-filled tweets from Drake fans. According to Drake he “always had a thing for her,” but we guess we’ll never know if what they had could’ve worked.

A Childhood Kind of Love

Drake likes to keep his love life as private as possible. However, if you listen closely to his lyrics, you may pick a clue or two. Just like in his song “Karaoke” where he mentions a wedding planner who he wanted to marry. This woman’s name was Jade Lee and she found herself in a relationship with the rapper during 2006.

The two had grown up together and held great affection for one another. She loved Drake but she couldn’t stand his lifestyle. According to her, it was all simply too much” for her which we’re sure anyone would understand! https://imasdk.googleapis.com/js/core/bridge3.500.0_en.html#goog_3336134846.5M76Kylie Jenner Announces Birth of Her And Travis Scott’s Second Child

A Relationship That Was Neither Confirmed nor Denied

While Drake likes to keep his love life private, it’s clear that he also likes to have people interested in it. His 2009 album titled So Far Gone, for example, was no different. So, if you’ve ever wondered which woman inspired “Bria’s Interlude,” we’re here to put you out of your misery.

The woman’s name is Bria Myles, a successful actress, and model. According to a 2017 interview with her, the two dated for a while back in 2009. Drake himself has neither confirmed nor denied having been in a relationship with her. However, we doubt that he would rap about her if he hadn’t.

An Unknown Love Interest

Who is Zineb Samir? To be honest, we’re not sure. All we know is that people call her Nebby and that in 2009, she was in a relationship with Drake. Other than that, the only information that we have is from his songs.

For example, in “Look What You’ve Done,” he says “It’s like ’09 in your basement and I’m in love with Nebby / And I still love her but it fell through because I wasn’t ready.” Not only that, but a few years later, his hit single “Hotline Bling” was rumored to have been about her as well.

Chemistry That Was Undeniable

If we had to make a list of our favorite artists that have performed together, Drake and Rihanna would be at the top of it. From the confession of his love and admiration for her at the 2016 MTV VMAs to their undeniable chemistry on and off the stage.

The problem is that neither has admitted to being in a relationship with the other. However, we have a feeling that they had been in an on-and-off relationship between 2009 and 2016. Not only has she featured in several Drake’s singles, but the two have been spotted sharing intimate moments on more than one occasion.

Drake Was Making Headlines

From what we can tell, Drake’s relationship with model Catya Washington was the real deal. The two met while on set for the video of “Best I Ever Had.” Almost instantly, they knew that they had a connection and started dating a month later. Unfortunately, Drake’s career was just starting to take off and the attention had him distracted.

According to Cat, they went to family dinners and did grocery shops together. Then, things started to change. She said that “He pops up in tabloids…with Malia. Trips to Jamaica that I wasn’t invited to and never heard about.” Real feelings were involved and Cat was certain that one way or another, it was going to end in heartbreak.

A Fling That Ended Badly

In 2010, Drake got involved with an exotic dancer named Maliah Michael. For those who are familiar with Drake’s work, you may recognize her from his “Find Your Love” video. In true Drake fashion, we don’t have much information on their relationship. But what we do know, is that it wasn’t an amicable breakup.

How do we know this? Well, all you have to do is look at her response when Drake “retired her jersey.” Michael immediately took to Twitter, exposing the rapper…and didn’t hold back! The dancer wrote, “Y’all don’t know that ni**a been trying to make me stop dancing. Always putting me down about it….Always telling me I’m not better than anyone else in the club selling a** instead of dancing. But ni**a can’t stay out the club…”

He Went to Court

Which court did Drake go to? Well, the tennis court of course! Especially during the time that he spent romantically involved with one of the profession’s favorites, Serena Williams. Between 2011 and 2015, Drake was spotted on the sidelines watching Williams play.

While the pair never confirmed that they were an item, photos of them kissing in a restaurant was all the information that we needed. What’s more, Williams featured in the Bottom’s Up, which was recorded in Drake’s condo. While we know that there is no chance of them rekindling their love, it’s nice to know that they gave it a shot.

A Bad Breakup Over Something Silly

For those who don’t know, Dollicia Bryan is an actress who has featured in a number of different films. Her career was starting to take off when she met Drake and the two hit it off. However, their fling was short and…not so sweet!

Apart from photos of the pair, the only other real information that we have is their reason for breaking up. Apparently, the couple split because Dollicia “didn’t think hazel-colored contacts were a good look” for Drake. There are two issues with that. Firstly, nothing could ever look bad on the rapper. Secondly, the fact that they let “colored contacts” end their relationship.

It Ended Before It Began

Are you a fan of America’s Next Top Model? If you answered yes, then chances are that you’re a fan of Tyra Banks! Fans were shocked when Drake revealed that the two of them had gone on a date in 2013. And, it wasn’t just any date.

Instead of going out to a fancy restaurant, they decided to do the complete opposite. They went to Disneyland…in disguise! While both Drake and Tyra had fun, they knew that it would never work. So they called it quits romantically, but continue to have a solid friendship.

Caught Canoodling in the Corner

In 2013, Beyoncé performed a live concert. As you can only imagine, people couldn’t take their eyes off of her…until something caught their eye. Way back in the corner Drake and Zoë Kravitz were looking awfully close.

It was only later that year that the actress shared her updated relationship status, describing Drake as “sweet” and a “cutie.” While their relationship only lasted until 2014, they gave it another go in 2018. Their second attempt at a relationship was even more short-lived than their first and they decided to take that as a sign.

Unsure of What He Wanted

Remember the days that people used to fight with their fists? Now, all you have to do is log online and type something. This is exactly what Drake did when he tweeted that he had “smashed” Blac Chyna. While it was meant for her boyfriend at the time, Drake put it out for all to see.

Chyna’s response confirmed our suspicions when she tagged Drake in a provocative picture. She even captioned it “Miss Me……#neverforget.” Aside from this online feud, Drake and Chyna have been seen looking very cozy together.

Soon Two Became Three

In 2017, Drake’s whole life changed. While it changed in a good way, it also became a lot more complicated. His son, Adonis Graham, was born on October 11. The complication comes in with the mother of his child, Sophie Brussaux.

Brussaux was an adult film star who Drake had seen twice before. While he didn’t want to make a habit of seeing her, getting her pregnant prevented that from happening. Nevertheless, he has stepped up as a father and loves his son more than anything.

Dinner and a Crush

In 2005, Drake was trying to kick start his career in the entertainment industry. During this time, he appeared in a drama series called Degrassi: The Next Generation where he met actress Tika Sumpter. While we can’t be certain that the two were romantically involved, we do know that they went for dinner.

According to Sumpter, “I have a slight crush on Drake. I’ve known him for a really long time.” She even described him as a “genuinely sweet guy.” While some say that they were involved while filming the series, we simply don’t have enough information to draw that conclusion.

Leaving It the Fans’ Imagination

Teyana Taylor is a singer, however, her voice isn’t the only thing that people have been talking about. What seems to be more interesting than her talent is the rumors of a love connection involving herself and Drake.

In 2009, Taylor posted a photo that looked a little too close to be “besties” as she had captioned it. Then again in 2013, Drake shared a photo of them cuddling. We’re not sure what to think and we’re not the only ones.

If Only He Were Older

Today, Taraji P. Henson is probably remembered for her role as Cookie in Empire. However, the talented actress has a long list of masterpieces that she’s been involved in. Everything about her screams strong and independent woman…which is probably what caught Drake’s eye in the first place.

In 2012, the actress addressed rumors of their involvement, claiming that they were just good friends. However, she did add that if he was a little bit older, they may have given it a go.

There Has to Be Something More

In 2009, Nicki Minaj and Drake had both just signed to Lil Wayne’s Young Money label and were the names on everyone’s lips. During that time there was one question on everyone’s mind and it revolved around when these two were going to get together. Both artists insist that they were never in a relationship, but here are some of the reasons why we think they weren’t being completely honest.

In Drake’s album called Take Care, he talks about having a crush on Minaj and wanting to marry her. Then, in her hit single “Anaconda” Drake can be seen lap dancing. While to us, this all indicates that they were more than friends, the two insist that they are “like family.”

They Could’ve Been Something Great

Can you picture a world where Rita Ora and Drake were an item? Well, it seemed that it almost happened back in 2012. Talk about a power couple! Many believe that the pair were actually dating when Drake wrote Ora’s hit single “R.I.P.”

Then, when Ora appeared in Drake’s “The Feeling of Pain” video people were convinced that it was true. Once people saw the connection that they two shared, it was hard to believe that they weren’t involved. While neither party has commented on their relationship status, we’d like to believe that it was real.

Was It a Fling or Was It Love?

We know that this list is getting long, but hold onto your hats because we’re only halfway through! Next on the list is Drake’s rumored relationship with Cyn Santana. For those who are unfamiliar, Santana is a model and star on the hit reality show Love & Hip Hop.

We know that they met each other on set while filming the “No Lie” video in 2013. Whether they classified their time together as a relationship or a fling, we can’t be certain. However, months later, they were then spotted spending quality time together. It also later came out that Drake’s song “Company” was written about Santana as well. Sounds like it was more than a fling to us!

Talk About a Birthday Surprise

Birthdays are a big deal for anyone but it’s not necessarily something that the press is interested in. Unless Drake shows up with champagne and some birthday love. In 2013, Drake surprised Tatyana Ali for her birthday and everyone went crazy over it.

He even referenced her in his son “ Tuscan Leather” where he said, “The Fresh Prince / just had dinner with Tatyana, no lie / all these ’90s fantasies on my mind / the difference is that with mine / they all come true in due time.” The twist comes in when Ali publicly denied having ever hooked up with the rapper.

Bernice Burgos is a successful American model who also happens to be one of Drake’s rumored girlfriends. While Bernice shut the rumors down in 2017 claiming that the two were “just friends,” we have evidence that says otherwise.

In 2015, the two were photographed kissing while on a trip to Australia. While we can’t be sure that this kiss led to anything more, we’re not convinced that their relationship was purely platonic. All we have is that photo and the statement from Bernice. Which do you believe?

A Little Too Close to Home

While Drake and Blac Chyna were actually dated, we know that they were once involved with one another. In that, we can only assume that he got close to her friends as well. That’s why we find this rumored love interest believable. After his fling with Chyna, many believe that Drake moved on to her best friend, Amber Rose.

In 2015, the two were spotted partying together on New Year Eve. However, since rumors began, both have denied any involvement. Whether they were trying to keep it under wraps or nothing actually happened we’re not sure…that’s for you to decide.

They Couldn’t Stop Smiling

While today, we know her as Justin Bieber’s wife, back then she was just model, Hailey Baldwin. You’re probably wondering why she made it onto the list or why you never heard about their involvement. And that’s because it’s all just speculation. In 2016, the two were spotted hanging out over Memorial Day weekend.

Not only did they seem to be having a great time together, but according to Entertainment Tonight, they were “totally engrossed in conversation.” With permanent smiles on their faces, we understand why people assumed that something was happening between them.

Stuck in a Love Triangle

Even if Drake had his eye on Hailey, she already had hers set on Justin. So, Drake had no choice but to move on…and it seems that he did with the Instagram model, India Love. little did he know that this was going to land him slap bang in the middle of a love triangle!

In 2016, the short love affair between India and Drake happened in between his on-and-off relationship with Rihanna. The plot twist comes in when we find out that India’s ex-boyfriend may have cheated on her with Drake’s complicated love interest Rihanna! Drake later confirmed their involvement but claimed that all so that she could get more followers on social media.

A Rumored Iconic Fling

We dare you to try and find a person that doesn’t like Jennifer Lopez. The only thing is that her list of boyfriends is almost as long as Drake’s list of girlfriends! And many believe that they appear on each other’s lists.

In 2016, Jennifer was seen supporting Drake at his Vegas show and even posted a photo of him on her Instagram page. While a relationship between the two would have been an iconic one if there was a fling it didn’t seem to last long. This was confirmed in Drake’s 2017 single “Diplomatic Immunity” where he says “I lost a J. Lo.”

He Carries Her With Him

In 2017, you may remember Drake’s Boy Meets World tour where he performed live 43 times. For his show in Birmingham, Jorja Smith opened for him and got the crowd all riled up. However, many believe that at the time, the crowd wasn’t the only people that she got riled up.

It was rumored that Jorja and Drake were dating and that he even got a tattoo in her honor. Amongst all of his tattoos, you’ll notice the number 11 which also just happens to be her birth date. The question that we’re asking is whether or not his song “Jaded” is about Jorja.

Taking a Stroll Down the Red Carpet

Any NBA fan will know Rosalyn Gold-Onwude. This sports broadcaster not only has one of the coolest jobs but is also the envy of women everywhere. While Drake and Rosalyn claim to have just been close friends, there was something different about her that set her apart.

According to sources, Drake “liked how normal she is, and she has her head on straight.” That’s probably why she was the only other woman, besides his mother, that Drake has walked down the red carpet with. Their stroll in front of the press took place in 2017, during a time when Drake claimed that they “laugh and are enjoying getting to know each other.”

Four Months of Wining and Dining

Bella Hadid is known for being one of the highest-earning models in the world. However, in 2017, her modeling career wasn’t the hot topic, but rather her involvement with Drake. Unlike many of the other women on this list, Bella claims to have had a purely platonic relationship with the rapper.

However, we’re not convinced. Not only does Drake refer to her in his Scorpion album, but many believe that he actively pursued her for four months. The cherry on the top was when he threw the model a surprise 21st birthday party before ghosting her.

They Had a Lot in Common

Drake is always working on new music and sometimes we can’t understand where he gets all of his inspiration from. However, for some of his songs recorded and released in 2018, we may have the answer.

While spending time in London, Drake sought companionship in singer Raye. Not only was she in the same industry as him, but she is an incredibly talented songwriter. Whether or not they labeled their relationship (or if it even turned into one at all), is unknown. What we do know is that they were spotted sharing a number of dates around town.

Holding Hands and Going on Dates

Throughout this list, we’re able to see that Drake has a type. Gorgeous women with phenomenal bodies! And his love interest in 2018 was no exception. Malaika Terry is a bikini model who may or may not have been romantically involved with Drake.

We’re leaning towards the rumors being true since the two were spotted walking around Toronto holding hands and going on dates. At one point, Malaika was even using the rapper’s lyrics as her Instagram captions. However, when questioned about their involvement, Malaika denied it all, claiming (you guessed it) that they were just friends.

Unsure of What He Wanted

In 2018, Drake had been spotted loving on Malaika in Canada. While we thought that they looked smitten, looks must have been deceiving. As it turns out, Malaika’s weren’t the only hands that Drake had been holding.

Around the same time, he was seen leaving a restaurant with a woman by the name of Zmeena. As you may have already guessed, she is an actress and Instagram model. While it may not surprise some, we never took Drake for being a player. Either way, none of the relationships worked out so maybe the women found out about one another.

Keeping Up With the Kardashians

If the Kardashians move, the press knows about it. So, when Drakes “In My Feelings” was rumored to have been about Kim Kardashian, it was all that people wanted to talk about. At the time, it all made sense since Drake and Kanye had bad blood at the time.

After his single was released, people assumed that Drake had slept with Kayne’s wife as revenge. Being a member of the Kardashian family, we’re sure that Kim is used to rumors flying around. However, when it started to affect her marriage, it crossed the line. She tweeted saying “Never happened. End of story.”

Spicy Instagram Live Sessions

As it turns out, Drake kept himself busy during 2018. One of his distractions that year was rumored to be British rapper, Stefflon Don. It all started over an Instagram Live when the two publicly shared some spicy texts.

According to sources, during the Live, Drake wrote “I’m a confident guy, I hold my own in any room, I’ve known you for a while, we buss ’nuff jokes together.” Later that year in November, the pair were seen looking a little too comfortable around one another at dinner in Miami. While it may not have lasted long, we’re pretty sure that something happened.

Enjoying Each Other’s Company

When Kim shut down the rumors about her being with Drake, he seemed to set his sights on another member of her family. Only this time, it was her sister, Kylie Jenner. While all of the attention was on him for his birthday, all of his seemed to be on her.

According to a guest at the party, “They were joking around and Kylie was laughing. She seemed to be really happy and in a great mood and she and Drake seemed very comfortable with each other.” However, that’s where it ended and they were never seen together again.

Touchy-Feely at New York Fashion Week

Covid-19 may have affected many people’s love life, but it didn’t seem to have an effect on Drake’s. In 2020, Drake attended the New York Fashion Week. While his clothes were on point, so was his arm candy.

Drake’s attention was supposed to be on the models and it was…just not the ones on stage. The time that he spent there was less about the clothes and more about making a connection with model, Imaan Hammam. Footage shows the two getting awfully close, however, nothing seemed to come of it.

A Private Extravagant Date

As we welcomed in the new year, we couldn’t help but think about how Drake spent the end of 2021…with Johanna Leia. Johanna is a model and one of Drake’s most recent love interests. The two bonded over their mutual love of basketball and things just seemed to escalate from there.

After they had been spotted at a basketball game together, the rumors began to fly. Many believe that Drake pulled out all the stops and rented out the Dodger Stadium in Los Angeles. Why, you ask? Well, because they needed a cute place for date night!

Now that you know a little more about Drake and his many romantic connections, let’s take a look at his most iconic ex, Rihanna and get to know her better.

Rihanna: A Deeper Look Into the Beloved and Controversial Star

Global superstar Rihanna shot to fame in 2005 with the smash hit Pon de Replay, aged just 17. Since then, Robyn Rihanna Fenty has grown into one of the most successful musicians and businesswomen on the planet, even becoming the World’s Richest Female Musician in 2019, according to Forbes Magazine. She has diversified her empire and now counts a successful beauty and fashion brand, Fenty, among her successes, becoming the “first black woman in charge of a major luxury fashion house,” along the way.

Her undeniable success and extreme popularity have led to unwelcome intrusions into her private life though, for the most part, she has succeeded in keeping her private affairs away from prying eyes. Many fans are well aware of her rapid ascent to fame but her story before that is shrouded in mystery. Information about the star’s childhood in Barbados is difficult to find and Rihanna herself is deeply protective of her family and her secrets. Regardless, the secrecy which shrouds her past makes Rihanna even more intriguing. Though her success might look easy, the circumstances she grew up in were far from ideal. She has overcome plenty of struggles in her young life – but it is perhaps due to these hardships that have crafted her into who she is today.

Since then, Rihanna has been unafraid of controversy and seemingly welcomed negative press as a chance to respond with her customary sharp wit. Her love life with many high profile celebrities has been the stuff of tabloid fodder for many years and seems unlikely to abate now. With diva-like backstage riders, famous exes, and sassy clap-backs – there really is only one Rihanna.

A Troubled Home Life

In Rihanna’s own words, she recalls her childhood in Barbados as being “just a little island girl riding bikes, running around barefoot and flying kites in the cemetery.” But the family home wasn’t always so idyllic. Her father had a significant problem with alcohol which causes tense moments. Speaking to Rolling Stone in 2011, she said, “Fridays would be scary because he would come home drunk. He’d get paid, and half of it would go towards alcohol. He’d walk in the door, and it was all eyes on him.”

The singer said she could feel the temperature in the house begin to rise whenever domestic violence was around the corner. In an interview with ABC News she recalled, “[My parents] had a very abusive relationship. My dad was the abuser. [He hit her] on numerous accounts. I don’t want to say normal, but it wasn’t a surprise when it happened. She never went to the hospital… Domestic violence is not something that people want anybody to know.” Her mother was the primary victim for her father’s outbursts, though Rihanna recalled a specific occasion when she wished to stay at the beach for another 10 minutes. “He slapped me so hard, I ran home with his handprint on me,” she told Rolling Stone. “I couldn’t believe it. My mother saw my face, how traumatized I was. You know how, when you know you did something wrong, and you deserve to get beat? This was out of nowhere.”

An Entrepreneur in the Making

Despite her primary living as a musician, Rihanna is also a powerful businesswoman in her own right. She has endorsement deals with Nike, Gucci, and Clinique, as well as her own scent, Reb’l Fleur, and successful underwear and cosmetic lines. Her entrepreneurial spirit was fostered when she was young, especially by her father. As the eldest child, she was fiercely independent from a young age, and she was heavily influenced by her father who, “Taught me how to fish, how to swim, how to run, how to run. He really toughened me up.”

Rihanna’s father, Ronald Fenty, was a businessman. From when she was a child, Rihanna would watch him sell clothes out of his car. Sometimes, through desire or necessity, she would join him. In a 2011 interview with The Sun, the star’s father said, “She used to sell stuff on the side of the street like I did. She’d come outside of the store and put up a rack and sell hats and belts and scarves… She would also buy sweets, put them in packages and take them to school to sell to her friends for a profit.” This is undoubtedly where her entrepreneurial spirit began to show itself and her father wasn’t at all surprised when she ended up as a businesswoman.

A Family in Trouble

Rihanna’s father struggled with substance abuse throughout her childhood. He gradually progressed from alcohol to drugs which began to wreak havoc on the singer’s family home. She expressed her pain and sadness on Oprah Winfrey’s Oprah’s Next Chapter, saying “My family broke up because of his addiction. Even as a toddler, I learned that my mum and dad would argue when there was foil paper in the ashtray,” speaking in reference to drug packaging and paraphernalia. Apparently, his addiction was so severe that he bought drugs even when money and food for the family were running low.

At just nine years old, Rihanna walked in on her father smoking crack. In an interview with The Sun, Ronald Fenty elaborated, “I did have a drug problem and Robyn did walk in and see me taking drugs in our house.” He went on, “She was just a little kid and it made her look at me, and other things, differently. Around the same time, we were walking down the street with the kids and there was a guy sleeping on the sidewalk. Her mother said to Robyn, ‘Your dad is going to end up like that.’ I did not want my children to see me sleeping on the sidewalk so I started making the changes.” Though her father would go on to beat his addiction, it cost him his wife and severely damaged his relationship with his children. “I had to give up drugs for my family. I still kind of lost them,” he says.

Rihanna the Nanny

Rihanna’s upbringing was far from traditional, and she was exposed to certain things much earlier in life than most. Sadly, she saw and experienced things that would affect most adults, and she encountered them when she was still a child. By the time she was 16 years old, her mother had had to return to work to support the family following her father leaving the family home. As a result, Rihanna had to stay at home to look after Rajad, her younger brother. Whilst it inevitably caused the singer to grow up quickly, she looks back at the times with her brother fondly, saying that it was “probably the best summer I ever had.”

That summer would not be the last time she would act as a caregiver for her family. Rihanna is well known for her generosity with her family and has gifted her mother an enormous mansion willingly, but it’s not always a case of goodwill. During her 2008 U.S. Tour, her father was arrested for drunken behavior. Her father would’ve gone to jail following the arrest in California had Rihanna not intervened. She shelled out over $58,000 for him to attend a prestigious Malibu rehab program. Rihanna once revealed to Rolling Stone that her dad had previously sent her a text with nothing except for the prices for furniture he wanted for his house. “It’s fine,” she explained in an interview. “I’ll give my father anything. It’s not something that’s hard for me to help him with. It’s just, like – damn, Dad. Hi.”

Kids Can Be Cruel

Though now lauded as a queen around the globe, Rihanna didn’t always feel loved and admired as a child in Barbados. She was descended from a poor Irish community, via her father’s bloodline and the members of such were often referred to by derogatory slurs. The surname “Fenty” was a common surname from this group, so there was no hiding her heritage. Combined with her lighter skin tone than her peers, she was the recipient of much teasing at school.

In a 2009 interview with Allure magazine, Rihanna said, “I was cultured in a very ‘black’ way. But when I got to school, I’m being called white… They would look at me, and they would curse me out. I didn’t understand.” The future pop superstar didn’t always handle the teasing well and fought back on more than one occasion, sometimes with her fists. “I got teased my entire school life. What they were picking on I didn’t even understand,” she told Glamour magazine. “It was my skin color. Then when I got older, it was about my breasts.” Despite the hardships that plagued her school life, the constant bullying helped to prepare her for a life living in the spotlight, which can be cruel and unforgiving. She told Harper’s Bazaar in 2015, “This thick skin has been developing since my first day at school. It didn’t happen after fame; I could survive fame if I didn’t already have it. So sometimes the toughest thing in life is to be vulnerable.”

Good Girl Gone Bad

Rihanna’s home life remained volatile, with her father battling his demons of addiction and the fights at home increasing in severity and frequency. It is unsurprising that in this environment, her mental health began to suffer. The trouble at home was carefully kept private from the other children at school, but Rihanna began to withdraw from her peers just the same. According to Rolling Stone, she wouldn’t even talk or cry and her grades began to slip along with her health.

Though she had always been a straight-A student, according to her mother, it was around this time that she began to struggle. “She would suffer from these terrible headaches,” recalls her mother, Monica Braithwaite. “She had to get CT scans”, these intense headaches would continue from the age of eight until she was 14. The doctors struggled to diagnose the excruciatingly painful, migraine-like attacks, even believing her to have a brain tumor of some sort. But each time, the test or scan would come back negative. An answer came in an unexpected form. When her parents finally separated and her home life was no longer plagued with violent fights, the headaches finally began to abate. She has long believed that the pain was a result of the consistent emotional stress of dealing with her parents arguing and domestic abuse.

History of Violence

Sadly for Rihanna, domestic violence didn’t remain a specter that haunted her childhood. In February of 2009, the world was shocked as reports emerged that Chris Brown had abused Rihanna, his then-girlfriend. Photos were released by TMZ of her bruised face and were picked up by almost every major news outlet around the world. The huge public scrutiny led to the singer retreating from the public eye for a while.

Despite being his victim, when she was in isolation, Rihanna began to worry about Brown. “If I feel this depressed, then what is he going through?” she later stated to ABC News, “I had to protect him. I thought that I had to let him know, don’t do anything crazy. Like, just hang in there… The whole world hates him now. His fans, his career. He just, he lost me, I just need to let him know; don’t do anything stupid.” As is so often the way, the pair ended up back together and Rihanna faced strong criticism for the move. Rihanna had previously stated to E! News that she was “never going to date someone like my dad” and she expressed her disappointment in herself. She didn’t feel proud of the choices she’d made but felt that she had been overpowered by the love she felt for Brown. When speaking to ABC News, she expressed that she was aware of the far-reaching consequences of her actions. “It’s completely normal to go back. It’s not right. When I realized that my selfish decision for love could result in some young girl getting killed, I could not be easy with that part. I couldn’t be held responsible for going back.”

The Rumor Mill

The rumor mill is constantly churning around high-profile celebrities which range from exaggerated stories to bare-faced lies. As often occurs around female celebrities, relationship rumors seem to swirl around Rihanna and any male celebrity she is seen talking to. Whilst she was working on a cover story for Rolling Stone, Rihanna was dining in the same restaurant as Colin Farrell. Rumors had already been published that the two were exchanging salacious texts. As Farrell was leaving the restaurant, he jokingly said to her, “Our friends outside (the paparazzi) are gonna get some good mileage out of this. We’re gonna be texting each other all f****** night!” Clearly no stranger to rumors himself, Farrell was bang on the money. By the next morning, a number of tabloids had seized on the story and stated that the two celebs ate dinner together and were romantically linked.

As if tabloids and paparazzi weren’t bad enough, sometimes rumors about Rihanna came from within her private circle. After her abuse at the hands of Chris Brown, her father sold information to the press. Speaking to Vogue in 2011, she said “That was the first time. My dad went to the press and just told them a bunch of lies. Because he hadn’t talked to me after… That whole thing.” She added, “He never called to find out how I was doing, if I was alive, nothing… He went straight to the press and got a check. Like, what do I even mean to him?” Sadly, this wouldn’t be the last time that Ronald Fenty would sell private information about his famous daughter.

Daddy Issues

Perhaps unsurprisingly, Rihanna found herself spiraling into a dark place after her problems with Chris Brown. On Oprah’s Next Chapter, she revealed that she felt resentful and angry and was struggling to overcome the challenges. When questioned about how she managed to get through the bad time, she responded that she had repaired her relationship with her dad. After her parent’s divorce, she had grown apart from her father. “I was so angry at him,” she said, “I couldn’t separate him as a husband from him as a father.”

Despite the reconciliation, Rihanna’s relationship with her father remained tenuous and strained. Though in many cases, it wasn’t personal – it was business. Rihanna, according to CNN, had discovered that her father and his business partner, Moses Perkins, were using her brand and name (Fenty) in order to make money. The singer’s legal team repeatedly filed cease and desist orders. When that and personal appeals to her father failed, she filed a lawsuit. During the 2019 suit, the extent of her father’s deception came to light. He had reportedly launched a production and talent company in 2017, named Fenty Entertainment. He had also negotiated 15 unauthorized Rihanna shows in Latin America, including two at the Staples Center and one at the T-Mobile Arena, which totaled nearly $15.5 million. He even attempted to register a line of hotels under the Fenty brand name. The case was going to be moved to a jury trial in 2020.

Yet More Heartbreak

Around 2017, Rihanna appeared to find love once more. She had entered into a relationship with Hassan Jameel, the Saudi billionaire. The couple kept their relationship very private throughout. A source told People in 2017, “It’s hard for her to get close to anyone, but she seems very happy.” Despite their firm stance on privacy, there have been a number of public encounters that kept fans hanging on for more information. They went on a, now infamous, trip for pasta on Halloween whilst dressed as Kylo Ren and The Penguin; they had a romantic dinner date and private Amalfi Coast cruises whilst vacationing in Italy; they sat courtside at a Lakers game to celebrate the singer’s 31st birthday.

Sadly, three years into their seemingly perfect relationship, it seemed as though Rihanna was back on the market. It was reported in January 2020 that the pair had split. The wealthy businessman is now a member of one of the most exclusive lists in the world – Rihanna’s exes, which includes Chris Brown, Drake, and even Leonardo DiCaprio. But what went wrong for this picture-perfect couple?

Rihanna Comes Clean… Sort Of

In a candid interview with her Oceans 8 co-star, Sarah Paulson, in June 2019, Rihanna opened up for the first and only time about her relationship with Hassan Jameel. Though she didn’t mention him by name, she was sincere and forthright about her opinions on love and starting a potential family. When Paulson asked her simply who she was dating, Riri responded with a classic comment, “Google it.”

Paulson went on to ask if she was in love, “Of course I am.” “Well, what about marriage plans?” “Only God knows that, girl. We plan and God laughs, right?” And did she want children? “More than anything in life.” Perhaps the pair disagreed on these fundamental relationship points? According to a source who spoke to US Weekly in September 2019, it was more likely to be a personality issue. They said that “Rihanna and Jameel’s personalities mesh well together. They’re both so different, but it works for them.” Whilst opposites do attract, it often takes more than that for a relationship to work long term.

Work Interruptions?

During the aforementioned interview with Sarah Paulson for Interview magazine, Rihanna talked candidly about her journey with work over the previous few years. She had learned that she needed to take more time for herself. “If you’re not happy, you’re not going to be happy even doing things that you love doing,” she explained. “It’d feel like a chore. I never want work to feel like a chore. My career is my purpose, and it should never feel like anything other than a happy place.” She went on to explain that, “I got into a new relationship, and it matters to me. It was like, ‘I need to make time for this.’”

In the past few years, Fenty Beauty, Rihanna’s cosmetics brand, has changed the face of the formidable cosmetics industry. Despite this success in areas other than music, the singer hasn’t released an album since 2016 and her fans are growing impatient. She previously confirmed that a new “reggae-inspired or reggae-infused” album would be dropped in 2019, according to Vogue. As 2019 progressed, it became clear that her fans would have to wait a little longer to hear Riri’s new music. It has been rumored that her relationship began to feel like a chore and interfere with her music… Either way, only time will tell.

Drake Got That Hotline Bling

Drake and Rihanna have been mentioned in the same sentence so many times, it’s really amazing they’re not together through the sheer willpower of their fans. Whenever Rihanna is single, Drake seems to appear once again. Her relationship with the singer has always been complicated and in 2018 she spoke to Vogue about the friendship with the Canadian rapper. “We don’t have a friendship now, but we’re not enemies either. It is what it is.” This slightly cold revelation surprised many, but in October 2019, she made an appearance at Drake’s star-studded 33rd birthday party. According to an E! News source, “Rihanna made an appearance and stayed for several hours. She was with two girlfriends and was escorted to Drake’s table by security.” They added, “Her and Drake were talking for a while and were smiling and laughing. It seemed like a very pleasant interaction and they looked like they were having fun together as friends.”

The Shade Room, where the event was held, reported some very Drake-like behavior. He had McDonald’s delivered to the club for Riri and her whole crew. This thoughtful move began even more rumors swirling about the potential for a romantic rekindling between the pair – but not this time. An insider told Hollywood Life, “Rihanna is in such a great place with Hassan right now. And she’s at a point in her life where she doesn’t want to hold onto any past grudges or negative feelings she may have had about any of her exes.” Maybe next time, Drake.

Chris Brown Reappears

Everyone now knows the painful history of Rihanna and Chris Brown. The pair have been amicably separated for a number of years now. The rapper now shares a child with Ammika Rice, around whom there have been wedding rumors. But apparently, he has been struggling with the recent news of Rihanna’s new singledom. A source told Hollywood Life, “It’s bad timing, to say the least, because he’s in such a good place with Ammika. They’re trying to see where things could go with them, and throwing Rihanna into the mix is going to end any chance of that working out.”

The inside source went onto say, “Rihanna is [Chris’] first love, in a lot of ways, it would be a dream come true for him to get her back.” The world would have some pretty strong opinions on Rihanna returning once more to her previously abusive ex and the source seemed to agree, stating, “That ship has sailed and everyone is hoping Chris is smart enough to realize that.” It has also been speculated that the January 2020 break up might have been significant for Brown for another reason. With the Grammy’s approaching, Brown was inevitably reminded of the “incident” between himself and Rihanna. According to the insider, “He always takes this time to reflect on himself and see how much he has changed.”

Moving in Quick, A$AP Rocky?

The rapper A$AP Rocky appears to be very interested in Rihanna’s new status as a single woman. The pair were seen on the red carpet at the British Fashion Awards in early December 2019 and had reportedly been spending a lot of time together leading up to her split with Jamal. Rihanna, according to TMZ, joined the rapper at Rolling Loud in October, as well as his show in Sweden in November. Perhaps most notable was her appearance at his Brooklyn Yams Day benefit concert in January 2020. The concert took place mere hours after the news of her breakup broke.

According to various sources, there was already a romance simmering before the breakup news broke. The pair had filmed a famously PDA packed music video for his track Fashion Killa. E! News posted a picture following the Yams Day concert, showing the pair looking cozy. A source who spoke to Urban Islandz, “They’ve been dating since the start of December, they’re just good at keeping it under wraps.” Other insiders have their own insights into the split of Rihanna and Jameel. One source claims, “Believe it or not, they argue a lot about it. Riri is super busy, she hardly even [has] time to go into the studio and he is very busy too, running multiple businesses. It’s like one of those love stories that you want to root for but deep down you knew it was doomed from the start.”

Brand Under Fire

As mentioned, Rihanna is more than just a music sensation. She has acquired and honed in on her business skills throughout the years. One of her business ideas, her lingerie brand Savage x Fenty, has done extremely well, but came under fire during one of her runway shows.

During a release of a virtual runway show for her lingerie line, as part of the background, a song that included a hadith – a sacred Islamic text – was used. Coucou Chloe is the music producer for it. As can be imagined, a holy text and a lingerie show don’t quite mix, and many were offended. Apologies were offered and the song was removed from streaming platforms.

Outspoken RiRi

Rihanna has never kept her opinions to herself and has earned a reputation of being quite outspoken. In 2012, MTV tweeted “Yikes!” along with a picture of her smoking a rolled “cigarette” whilst perched on a bodyguard’s shoulders at Coachella. Her response? A tweet, informing the world that she had “run out of f**** to give”. Despite aiming the statement at one of the biggest news outlets in the music world, Rihanna remained as honest as ever. She has refused to apologize for her bold fashion choices and savage clap-backs to foes and fans alike. After appearing at an awards event in a – now-infamous – sheer, Swarovski crystal-encrusted dress, she was questioned about her decision not to wear a bra. Her response was that her only regret was not wearing a sparkly thong underneath too, instead of the nude underwear she chose instead.

Far from being embarrassed about her “savage” reputation, Rihanna has turned the phrase to her advantage. She now owns the world with pride, even naming her lingerie line “Savage”. Despite garnering much praise for her witty comebacks, biting commentary, and her fierce music, there have been moments where she has been criticized for going a step too far. Some have even labeled her as more of a bully than a boss.

Elaborate Backstage Demands

Like many superstars, Rihanna has a list of very specific items she needs backstage at each show or public appearance in order to perform at her very best. In a 2016 report from Business Insider, Rihanna has a number of slightly unusual requests. These include covering the walls with dark blue or black drapes that have been trimmed in “icy-blue chiffon” and a huge, plush animal print rug. The specificity of her demands has even led some to believe that a Fenty interior design line can’t be far away.

She has specified that her backstage area should have a “relaxed atmosphere” – not a big request, some might say. She allegedly has made her team work hard to keep her happy backstage, but being a worldwide phenomenon must be tough on a person. She is even specific when it comes to the scents she uses backstage, asking for precisely six Archipelago Black Forest candles. She also requests white tulips but has been flexible on that matter. If white tulips aren’t available RiRi is apparently equally happy with white Casablanca lilies or white freesias. Clearly producing epic performances requires an equally epic backstage space.

Reckless Spending

Despite her elaborate demands, Rihanna hasn’t always had her demands met, financially speaking. During her 2010, “Last Girl On Earth” tour, her accountants couldn’t keep pace with her spending habits. She blamed her accountants and even filed a lawsuit in 2012 according to Page Six. She claimed that the accounting firm showed “negligence that prompted a costly IRS audit of her returns and that she lost millions during the tour because the firm failed to reconcile costs versus revenues while still paying itself millions in fees.” The report goes on to say that the firm allegedly “gave her the green light to buy a $6.9 million Beverly Hills mansion, even though she was bleeding cash.” It later transpired in another Page Six report that the legal team alleged that the property was a “lemon” – and required over $1 million in renovations. She ended up selling the property at a loss and by the end of 2009, the songstress was down to her last $2 million.

However, one of her accountants mentioned in the Page Six report says that real events were completely different. In legal documents, he said, “The tour was what she wanted, just as the exorbitant amount of expensive clothing and other purchases she squandered her money on were.” He went on to say, “Was it really necessary to tell her that if you spend money on things you will end up with things, and not the money?” Despite seeking a $35 million payout, Rihanna reached a $10 million settlement with the firm in 2014.

Throwing Shade

The relationship between Rihanna and Drake has had its rollercoaster moments over the years. Despite collaborating on a number of hit songs (including Work, Take Care, and What’s My Name?), her attitude has always been remarkably cool, whereas he has evidently always nursed fond feelings towards her. During a 2019 cover story interview for Vogue magazine, she seemed to be throwing significant shade at him instead.

The magazine threw it all the way back and asked her about the 2016 MTV Video Music Awards. Drake was presenting her with the Michael Jackson Vanguard Award and waxed lyrical about RiRi during the lengthy speech, where he told the world that Rihanna was “someone I’ve been in love with since I was 22-years old, and she’s one of my best friends in the world.” But what did the songstress have to say about this outpouring of emotion? “Waiting through that speech was probably the most uncomfortable part, I don’t like too many compliments; I don’t like to be put on blast.” She went on to say, “We don’t have a friendship now, but we’re not enemies either. It is what it is.” Hopefully, Drake managed to take that blow gently.

Not Afraid to Clap Back

The rise of social media in recent years has enabled celebrities in the public eye to respond in kind to unkind tabloid stories. Rihanna has turned the “clap back” into something of an art form and numerous articles have been devoted to her online trolling antics. In 2017, Barstool Sports published an article entitled: “Is Rihanna Going to Make Being Fat the Hot New Trend?”. She responded quickly with a Gucci Mane meme depicting the rapper shirtless at various weights. She captioned the image: “If you can’t handle me at my 2007 Gucci Mane, you don’t deserve me at my 2017 Gucci Mane” in a modern twist of Marilyn Monroe’s classic quote. Her fans responded with praise (and over 600,000 likes) for how the star handled the situation and her devil-may-care attitude.

Even her fans, affectionately known collectively as the Navy, aren’t safe from the singer’s quick wit and trolling. Her followers had built up hopes of an album release in 2019 and as the year went on, it became increasingly clear that no album was forthcoming. Evidently, Rihanna wasn’t enjoying the ongoing queries about the no-show album because, in July 2019, she shared a video clip from Love & Hip Hop Atlanta. The clip showed reality TV star Karlie Redd sharing the results of a lie detector test, where she says, “Guys, it was all a lie.” Sharing the clip seemed to be a clear dig at her dedicated followers. One even responded with “I can’t believe I stan a liar…” Clearly, Riri still wasn’t bothered, only responding with three laughing emojis.

No One Is Safe From the Troll

Not even fellow celebrities are safe from Rihanna’s sharp tongue – or tweets. When Ciara, a fellow singer, reported to the Fashion Police that Rihanna had not been the nicest to her, Rihanna sent a savage tweet response: “My bad ci, did I 4get to tip u? #howrudeofme” Another dose of shade was doled out to actress Amanda Bynes in 2013. Bynes, who was suffering from mental instability and addiction at the time, went on a racially charged twitter rant about the relationship between Rihanna and Chris Brown. Rihanna appeared to refer to Bynes’s stability which had been making headlines at the time in her response, “Ya see what happens when they cancel intervention?”

Some of the shade dates back to 2014 when T-Boz and Chilli from girl group TLC appeared on Sunrise Australia. They ranted about female artists using their bodies in order to see music, singling out Rihanna and her famously skimpy outfits. “Every time I see you, you don’t have to be naked,” T-Boz said, making it clear that she was proud of TLC for making music history “with their clothes on.” Riri’s Twitter response was a picture of her sticking her tongue out with a caption stating “When there’s no changing the fact that I’m me, and they’re well… They’re them.” In a tongue-in-cheek further move, Rihanna changed her Twitter header picture to a photo of TLC during their 1994 VIBE photoshoot wearing very revealing outfits. Touche Rihanna, touche.

Don’t Stand So Close to Me

Perhaps one of Rihanna’s most famous blunders occurred at an infamous concert. During her 2013 “Diamonds World Tour”, she appeared to administer a bop to the head of a fan. There is footage available on YouTube which showed the singer performing her hit song We Found Love at a concert in Birmingham, England. During the performance, the singer walked through the crowd, to the delight of her thousands of screaming fans. One of those fans appears to get too excited and grabbed Rihanna’s arm as she walked by. Despite the presence of her security guard, Riri appears to react instinctively and seems to whack the concertgoer on the head with the sparkling gold microphone in her hand before continuing on her performance.

Whilst some fans preferred to believe that the microphone incident was an accident, Rihanna herself states differently. In a savage tweet, she said “Purpose! That b**** won’t let me go.” With an absence of comment from the person who was hit, her account stands.

Keep ‘em Waiting

Aside from the spiky wit which has become her trademark, Rihanna also has a reputation for treating her fans poorly over the years. At various concerts, she has forced fans to wait over two hours before performing and even then, doesn’t always appear to give her best performance. In a 2013 performance in the Netherlands during her “Diamonds World Tour”, she gave a lackluster performance after spending the day shopping in Paris according to Yahoo!. One music critic from Standaard likened her performance to “a Valium overdose”. They went on to say that the singer “rarely danced and murmured only a few of her famous lyrics during the show, leaving the rest to a backing track

She faced further criticism in 2016 during a performance at the Pukkelpop festival in Belgium. The self-proclaimed “badgallRiRi” was booed by 60,000 according to the Daily Mail after she allegedly turned up an hour late and lip-synced almost the entire show. Though Rihanna is undeniably one of the most famous female singers of all time, her