When Drake called himself a certified lover boy, he wasn’t kidding.
The Canadian rapper has had more flings with A-list celebrities than most, from Rihanna to Jennifer Lopez.
In December, the rapper even made a necklace with 42 engagement rings to reflect the times he considered proposing.
You’re probably curious about his count, so let’s get started!
SZA
In his 2021 song “Mr. Right Now,” Drake said he dated singer SZA in 2008.
He wasn’t bluffing–the singer confirmed they dated, though it was 2009 and not 2008.
SZA said they are still friends, and things have never been weird since they broke up.
Ericka Lee
Between 2010 and 2011, Drake dated Ericka Lee–the voice in his song “Marvins Room.”
Lee sued the rapper in 2012, claiming he was keeping her from their co-writer royalties.
The pair settled out of court in 2013, but the rapper didn’t forget.
The rapper mentioned Lee in his song “Redemption,” saying she started a business after suing him.
Kat Dennings
Thirst tweets never work–unless you’re Drake.
He sent “2 Broke Girls” star Kat Dennings a 5 am tweet letting her know she was a dime on the Conan talk show.
The rapper later revealed he’d had a long crush on the singer, so he was ecstatic when they went out on a date.
Tyra Banks
TV personality and iconic model Tyra Banks went on one date with the Canadian rapper in 2012.
They disguised themselves and went to Disneyland, though one thing didn’t lead to another.
Instead, they became great friends and are still close, with Tyra appearing in Drake’s 2016 music video, “Child’s Play.”
Rihanna
Before becoming a billionaire, Rihanna dated Drake on and off for ten years.
They first met when Drake was an extra in her 2006 hit song, “Pon de Replay.”
However, they didn’t get together until 2009, when paparazzi spotted them on a date at New York’s Lucky Strike bowling alley.
At first, Rihanna shut down rumors they were dating.
However, they collaborated and performed together for the next few years and were spotted cozying up at a nightclub.
In 2013, Drake seemingly confirmed they had broken up by speaking about Rihanna in the past tense.
In 2016, though, Rihanna’s “Work” came out, and the pair were back on, though they tried keeping it secret.
Secrecy didn’t last long, and Drake publicly accepted he’d been in love with Rihanna since he was 22.
By 2018, however, their relationship was once again on the rocks.
They no longer spoke but weren’t enemies.
View this post on Instagram
Rihanna has moved on, having a baby with rapper A$AP Rocky.
Hailey Bieber
In 2016, the Canadian rapper snuggled up with model and socialite Hailey Bieber.
They met a few weeks later and were reportedly dating casually.
However, things didn’t work out, and Hailey married Justin Bieber.
Jennifer Lopez
In December 2016, rumors flew that Drake and J-Lo were dating.
J-Lo was smitten by the rapper, and they took things slowly.
That New Year’s Eve, the rapper gifted her a $100,000 necklace, and they celebrated together.
The pair were close in January, but the fire fizzled out in February.
Sophie Brussaux
After splitting up with Jennifer Lopez, the rapper was on the hunt again.
He soon had a fling with painter and ex-adult film star Sophie Brussaux.
On May 2017, Brussaux revealed she was pregnant with Drake’s kid.
Even though the rapper denied it publicly, he supported Brussaux shortly before she gave birth.
On March 2018, a paternity test proved he was the dad.
Since then, the rapper has proven he’s a devoted dad by spending time with his son and Brussaux.
Kylie Jenner
Drake has known Kylie Jenner for years, but their friendship grew into something more in 2019 when Jenner was on a break from Travis Scott.
Though no one has proven that the pair had a fling, they did spend plenty of time together, and rumors were rampant that they were casually dating.
Julia Fox
Actress Julia Fox was open about briefly dating Kanye West.
However, she kept her short fling with Drake hush-hush.
On a podcast in 2022, Fox revealed they were hanging out, not dating.
However, Andy Cohen made Fox admit Drake was her favorite celebrity date–he took her aboard a private jet and bought her Chanel bags when they landed.
Johanna Leia
In 2021, the “Hotline Bling” rapper dated the mom of hot basketball prospect Amari Bailey, Johanna Leia.
They made their relationship public that July and Drake mentored her son Bailey.
However, their relationship didn’t last long–in a recent interview, Leia revealed she was single and searching.
Drake Has Been Around
The Canadian rapper has dated a dozen A-listers, so he’s undoubtedly a modern-day Casanova.
However, time is moving, and many of his exes have settled down.
Hopefully, Drake will find that special someone sooner than later.
