Rihanna has made relationship headlines with fellow musicians Drake and A$AP Rocky, but
you’ll never guess which billionaire businessman she credits for changing her life for the
better.
Let’s take a deep dive into the "Umbrella" singer's both confirmed and rumored relationship
history.
Rihanna's first boyfriend, Negus Sealy, dished on their relationship to the Daily Mail.
According to Sealy, he first met the singing sensation through a friend when she was a
mere 15-years-old.
The 2011 interview has Sealy's age down as 27, meaning that he was 19 when he first locked
lips with Ri.
Saying of his romance with Rihanna, Sealy said -
"She would be the perfect girlfriend and of course I fancy her — what guy wouldn't?
She's absolutely amazing and gorgeous and she has a very, very strong persona.
I am so lucky to have spent so much time with her.
[…] But right now she doesn't have time for anything serious with any guy."
Radar reported that the former teen lovers had rekindled their romance in 2011, noting
that Rihanna engaged in some highly suggestive dancing with her ex while on holiday in Barbados.
However, Rihanna biographer Sarah Oliver has put these rumors to bed, emphasizing that
the pair are merely good friends.
Remember Josh Hartnett?
Everyone's favorite early 2000s pretty boy was reportedly getting super cozy with RiRi
circa 2007.
At the time, Rihanna gushed about having her heart set on Hartnett.
According to the Mirror, during an appearance at the World Music Awards, Rihanna apparently
said of Josh -
"I've fallen for him big time.
I would be lying if I told you we were not more than just friends.
He is so hot and he is really sweet to me.
When we hang out it feels right — even though it's still pretty new."
However, she later emphatically said that the pair were not dating, telling Allure -
"I went to [the New York club] Pink Elephant, and he came by.
All of a sudden, the next day, I'm seeing that we were kissing and hugging up each other.
You can't even go out with a friend who's a celebrity and have a good time without people
making s— up.
Well, at least he's good-looking, right?"
For his part, Hartnett has also denied that anything went down between the two.
"No, Rihanna and I never dated."
"Thank you!
Doesn't that feel good to get the truth out-out there?"
"I was never - I was never pretending I was never playing coy."
A couple of years later, Rihanna was also linked to Shia LaBeouf, who dished on their
one and only date to Playboy.
The actor claimed that he didn't pursue a relationship with Ri beyond the first date,
saying -
"The spark wasn't there.
We weren't passionate about each other in that way."
Considering LaBeouf's shocking behavior in recent years, we can't help but think this
was for the best.
According to Hollywood Life, Rihanna and Chris Brown first met as teens with dreams of fame
and fortune.
According to CNN, they began dating and went public with their romance in 2008.
But things took a devastating turn when it was revealed that Brown had viciously beaten
Rihanna.
According to The Guardian, Rihanna and Brown were supposed to perform at the Grammy Awards
in 2009, but they mysteriously pulled out.
It soon became quite apparent why.
TMZ obtained an official police report, which detailed the extent of Brown's brutal assault
on his then girlfriend, and published photos of the singer's horrific injuries.
Brown agreed to a plea deal for the charge of felony assault and was given 5 years probation.
A year after the traumatic ordeal, Rihanna reflected on surviving the abuse in an interview
with Marie Claire, saying apparently in the midst of tears -
"Eventually, I remember waking up one day and I knew I was over it.
I was very lost.
I have to say I felt really confused.
I hate talking about it but it was really crazy because I felt so out of touch with
myself.
[…] It's scary because nothing you say or do feels like it's you."
The confusion that Rihanna felt is typical of many survivors of domestic violence, as
highlighted by The Mend Project.
In opening up about her experience, Rihanna helped to amplify the voices of domestic abuse
survivors.
"I didn't cause this.
I didn't do it.
This happened to me and it can happen to anybody."
Drake has made no secret of his infatuation with Rihanna over the years.
The pair were linked in May 2009 when Page Six reported that they were hanging at Lucky
Strike where Ri was allegedly drinking and loving on Drake throughout the night.
However, as Drake revealed at the VMAs, they first met years earlier, when Rihanna was
filming the music video for "Pon de Replay" in Toronto, as Drake revealed at the VMAs.
The couple had frequent ups and downs, with Drake often complaining about his ex to the
press.
In 2010, he claimed to The New York Times that Rihanna had used him, and then a year
later, he told Elle that Rihanna had hurt him.
But despite his claims, it was clear that Drizzy was dizzy in love.
At the 2016 VMAs, Drake gushed about Rihanna when presenting her with the Vanguard Award,
saying -
"She's someone I've been in love with since I was 22 years old."
As he spoke, Rihanna rolled her eyes, not looking entirely enthusiastic about this bold
declaration of love in front of a live audience.
Sure enough, Rihanna admitted in a Vogue interview that Drake's speech made her feel uneasy,
saying -
"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."
When asked whether she was still close with Drizzy, she revealed,
"We don't have a friendship now, but we're not enemies either."
In 2009, Rihanna reportedly found comfort in a new man, basketballer Rashard Lewis.
An insider spoke to Daily News, saying -
"Rihanna is trying to get to know Rashard.
She's digging on him, and she hopes the feeling is mutual."
Alas, nothing seemed to materialize between the two beyond this gossip.
Don't think this meant Ri was left alone though — around this time, she was also linked
to Justin Timberlake.
Outlets reported that Timberlake was cheating on Jessica Biel after rumors surfaced of RiRi
apparently giving JT a private lap dance at a club.
A source told Hollyscoop -
"He is really into her.
Justin and Rihanna have been seeing each other for the past few weeks."
The following year, rumors persisted, with an alleged pal of Rihanna telling Daily Star
that she and Timberlake were getting close.
The insider claimed that things were super steamy between the purportedly lusty pair,
alleging -
"Rihanna called a friend and said she had a sexy little secret to share.
She started laughing and said, 'Don't trip, but I have hooked up with Justin.'
She said it was really good, hot and wild and that they have some of the best make-out
sessions she's ever experienced."
But considering that the duo have worked together, it seems unlikely that these sightings were
anything other than friendly outings between musically blessed pals.
During a 2017 Instagram Live, mid-2000s hip-hop one hit wonder Soulja Boy cranked out some
absurd claims.
The rapper told his millions of Insta followers that he was responsible for the rift between
Chris Brown and Rihanna, with whom he claimed he had a tryst a few years earlier.
Soulja Boy alleged that Chris Brown had called him while he was in a hotel room with Rihanna
and asked if he was with her.
Then, apparently addressing Brown, Soulja Boy said -
"Nobody would have known […] if it wasn't for you.
You're an idiot.
You exposed yourself."
Soulja Boy appeared on "Hollywood Unlocked" to further address his supposed relationship
with the "Diamonds" star, claiming that she was the one who initiated their fling after
calling his management team.
The rapper then alleged that Rihanna called him and invited him back to her hotel room
at 1am, dressed in a skimpy robe, before confiding in the rapper about Chris Brown's violent
treatment of her.
Soulja Boy alleged that all of this led to his beef with Brown.
"And that's what the - I'mma be real with you, that's what the beef really stems from,
it stem from Rihanna."
It should be noted that Rihanna hasn't confirmed any of Soulja Boy's assertions, a classic
case of he-said, she isn't going to talk about it.
Rihanna and baseball star Matt Kemp dated for around a year and appeared to be quite
the lovestruck power couple.
They first met through mutual friends in late 2009 and according to People, it didn't take
long for the pair to hit it off — no pun intended.
In 2010, RiRi gushed about the exciting new relationship in an interview with Elle, saying
-
"I have a boyfriend.
I'm so happy.
I feel really comfortable, and it's so easy.
I have such a chaotic life, but at the end of the day, that is just my peace.
It keeps me sane, really, talking to him and talking to my family."
Kemp seemed to be equally smitten, telling Us Weekly -
"Yeah, that's my girl!
She's just a fun person.
I love to be around her.
She's a great person in my life and I'm happy I'm with her."
Sadly, despite their mutual fervor, the couple called it quits at the end of 2010.
An insider told Us Weekly that Rihanna had allegedly just had enough of the relationship.
They added that Kemp struggled with the singing superstar's hectic lifestyle, saying -
"He just can't keep up with her crazy travel schedule.
Matt's sick of always following after her like a puppy dog all over the world.
He wants something more normal."
Kemp also didn't seem thrilled with the extra media attention that the relationship brought
him.
"There's so much attention for so many simple things that, I mean, I just want to be regular
man, like I wanna live a regular life."
In 2011, Rihanna was apparently feeling hot and bothered over boxer and model Dudley O'Shaughnessy.
During her time in the U.K., the Daily Mail reported that Ri was partying with the brooding
Brit well into the early hours of the morning and the two left together in a limo.
She had previously set sights on the hunk when filming her music video for "We Found
Love," which stars O'Shaughnessy and sees the pair engaging in a series of passionate
make-out sessions before things take a darker turn.
But, according to insiders, Rihanna could hardly cover up her lust for her co-star,
with an insider telling The Sun -
"Rihanna was making no secret that she fancied the pants off Dudley.
They hit it off straight away.
She had seen his modeling shots and other pictures when he was a boxer.
Rihanna took every opportunity to get close to him and at one point she was sitting in
his lap during a break from filming."
However, it seems that Rihanna's supposed interest didn't manifest into a relationship.
During an appearance on "The Ellen Show" at the time, the host showcased a photo of O'Shaughnessy
and his steely peepers, but Ri firmly insisted that she wasn't dating anyone.
Ashton Kutcher has certainly attracted some of the entertainment industry's finest over
the years.
Before he tied the knot with Mila Kunis and after his marriage to Demi Moore, he was linked
to Rihanna.
In 2012, Radar reported that Rihanna was seen leaving the newly single Kutcher's home in
the early hours of the morning after a four hour visit.
The Sun then claimed that the pair had been enjoying a fling, with a source alleging -
"The flirting began as soon as Rihanna and Ashton met and swapped numbers.
That moved onto texts and arranging to meet.
They snuck off to a Santa Monica hotel a few weeks ago."
The insider went on to purport that RiRi was studying Kabbalah for Kutcher, claiming -
"If she and Ashton are getting really close, she wants to be able to understand it."
During a press conference for "Battleship," Rihanna was asked to address the rumors, and
accompanied her answer with some major side-eye toward the reporter.
"Wow, how disappointing was that question?"
"Shall we move onto another one?"
"Absolutely."
"I think there was a quest - we're gonna move on I think there's a question -"
"I'm happy and I'm single."
Karim Benzema is a French international soccer star, who plays for Real Madrid.
The sportsman was linked to Rihanna in 2015, though their apparent romance seemed to fizzle
after less than two years.
In June 2015, E! reported that the pair were enjoying a summer of love.
After being snapped snuggling at a restaurant, an onlooker dished on their dalliance, saying
-
"Rihanna and Karim were sitting across from each other.
There were about four people at the table and a few more in another table from the same
party.
They came separately and they were speaking French at some point."
The following month, E! reported that the pair were taking things slow but enjoying
their time together, adding -
"They have an amazing connection and always have a wonderful time when they are together."
In 2017, those close to Benzema said the couple had called it quits.
Sources told Spanish mag Don Balon Rosa that it was Ri who called off the relationship,
apparently telling her beau that she simply wasn't over her ex, Chris Brown.
An insider alleged -
"Rihanna loved Karim, and with him she had a lot of fun.
But she told him she did not want to break his heart, and she confessed that she'll always
love Chris Brown.
Rihanna said it was difficult to compete."
According to Page Six, Formula One champ Lewis Hamilton was spotted getting close to Rihanna
after snaps surfaced of the pair vacationing in Barbados in August 2015.
There was a touch of overlap between her romance with Karim Benzema and alleged dalliance with
Hamilton, with a source telling E! -
"Rihanna is dating now and she hasn't put a label on anyone.
She is still talking to Karim but she is also talking to Lewis and keeping her options open.
She is not at any point in her life now ready to settle just for anyone but she is enjoying
the time she has with her friends and also focusing on work."
Accordingly, Page Six reported that the two appeared rather intimate at a nightclub.
When E! asked the champ about the status of his relationship with Ri, he said -
"I've known Ri for a long time.
We've been friends for a while.
We get to hang out every now and again."
The alleged romance appeared to wane some time after.
In 2018, Hamilton admitted to The Times -
"When you travel as much as I do it's hard to keep up a relationship."
During a seemingly more simple time in his life, Travis Scott enjoyed a low key romance
with Rihanna.
In September 2015, E! announced that Rihanna and Scott were dating, with a source claiming
-
"It's already very serious.
He's very into her."
TMZ published snaps of the rumored couple in the throes of a steamy make-out sesh at
a fashion week afterparty.
It seems that Rihanna's eagerness to pack on the PDA with Scott may be due to their
alleged chemistry in the bedroom, with a source telling Hollywood Life -
"Rihanna and Travis are uncontrollable."
In an interview with Complex, Scott remained coy when asked about RiRi, but he did describe
his reported lady love in glowing terms.
The outlet also notes that Scott was tardy, allegedly because he'd been delayed by Rihanna.
Complex editor Lawrence Schlossman later said that Scott was infuriated with him for revealing
his romance with Rihanna, saying on the "Throwing Fits" podcast -
"I broke the news about him and Rihanna, which they told me not to do."
Why?
Well, as Schlossman alleged, Rihanna was apparently embarrassed for the public to know she was
dating Scott, hence their lowkey romance.
According to Forbes, Hassan Jameel is a Saudi businessman with a whopping net worth of almost
$2 billion thanks to being a member of the 12th richest Arab family in the world.
He was first linked to Rihanna in 2017 after People reported that the two were spotted
smooching during a coffee date.
The attractive couple then celebrated Halloween together, with an onlooker telling People
-
"Rihanna and Hassan were canoodling all night."
One of Rihanna's most serious relationships, she and the wealthy businessman were going
strong for years.
Speaking with Sarah Paulson for Interview Magazine in 2019, Rihanna said the romance
changed her life for the better.
Notably, she had finally been able to make time for herself, explaining -
"I got into a new relationship, and it matters to me.
It was like, 'I need to make time for this.'
Just like I nurture my businesses, I need to nurture this as well.
[…] On my calendar we now have the infamous 'P,' which means personal days."
When Paulson asked Ri about the seriousness of the entanglement, the songstress confirmed
that she was in love with Jameel.
Sadly, Us Weekly reported that the couple had parted ways in January 2020, after a grand
total of nearly 3 years.
Sources told People -
"Their lives were too different and it was hard to maintain a relationship."
Talk about musical power couples.
Rihanna and A$AP Rocky were initially spotted getting close at a concert in New York in
2020, though they first collaborated almost a decade earlier on the remix for the saucy
track "Cockiness (Love It)."
Shortly after her split with Hassan Jameel in January 2020, a source dished to The Sun
about Rihanna's new liaison, revealing -
"They shared a hotel suite during that trip in New York.
However, Rihanna is reluctant to put a label on it as it's so soon after Hassan.
They're really enjoying each other's company and taking things easy as it's still early
days."
"What is your skin type?"
"Handsome."
By December 2020, People reported that the pair was going strong, and in an interview
with GQ, Rocky declared his love for Ri, saying -
"The love of my life.
I think when you know, you know.
She's the One."
In January 2022, Rihanna and Rocky revealed that they were expecting their first child
after the stylish duo were snapped cradling Ri's baby bump.
A source told People -
"Being with Rocky opened her up to the idea.
She couldn't be happier and is so excited to be a mom."
The announcement appeared to spark jealousy in Rihanna's ex, Drake, who swiftly posted
a series of cryptic, morose posts on Instagram.
It seems that some people just had to rain on Ri's parade.
Sorry Drake, you'll never be under her umbrella.
If you or someone you know is dealing with domestic abuse, you can call the National
Domestic Violence Hotline at 1−800−799−7233.
You can also find more information, resources, and support at their website.