For many years, the romance between Drake and Rihanna excited fans, with the two musicians fueling rumors about the nature of their relationship through many interactions and collaborations. However, they largely kept their personal details private.

Their relationship timeline was filled with moments of passion, heartache, and everything in between. From their dates in New York City to their steamy performances at award shows, Drake and Rihanna kept fans guessing about the true nature of their connection.

Drake - God's Plan
Drake – God’s Plan | via Drake YouTube

However, Drake once opened up about once envisioning a “fairy tale” future with Rihanna that involved starting a family together, a dream that never materialized, as the singers went their separate ways.

Drake and Rihanna’s Decade-Long Connection

Rihanna - Work ft. Drake
Rihanna – Work ft. Drake | Via Rihanna YouTube

In a 2018 interview on LeBron James’ HBO series The Shop, Drake admitted:

“As life takes shape and teaches you your own lessons, I end up in this situation where I don’t have the fairy tale, like, ‘Oh, Drake started a family with Rihanna and this is like so perfect.’ It looks so good on paper. By the way, I wanted that too at one time.”

Also read: Drake Reacts to Kendrick Lamar’s Euphoria With a Warning That Proves Their Rivalry is Not Even Close to Being Over

His candid confession showed how serious his feelings were for the Barbadian singer at one point. Drake and Rihanna’s connection dates back to 2005 when a young Rihanna shot the music video for her debut single “Pon de Replay” at a Toronto diner, where Drake made a cameo. This early interaction planted the seeds for their flirtatious friendship and with hints of an occasional romance over the next decade.

Their chemistry was sensed from the first time they collaborated on the 2010 hit “What’s My Name?” The song’s lyrics and music video depicting the two getting cozy fueled dating rumors that stayed for years. More collaborations and joint performances followed, and their set at the 2016 VMAs, where Drake openly talked about his love for Rihanna while presenting her with the Michael Jackson Video Vanguard Award. He said,

“She’s someone I’ve been in love with since I was 22 years old. She’s one of my best friends in the world. All of my adult life I’ve looked up to her even though she’s younger than me.”

Also read: “We don’t have a friendship now”: Rihanna & Drake No Longer Friends after She Wouldn’t Kiss Him at 2016 MTV VMAs

However, behind the scenes, both continually left fans guessing about their true relationship status. They were often spotted together looking coupled up one month, only to be reportedly “just friends” the next. According to People, sources confirmed they were officially dating in 2016, with one calling it an “open thing,”. It was 2018 when Rihanna declared they were no longer friends.

Drake and Rihanna Moved on to New Relationships

A$AP Rocky with Rihanna in Fashion Killa
A$AP Rocky with Rihanna in Fashion Killa | Via ASAPROCKYUPTOWN YouTube

After their split, both Drake and Rihanna embraced new partners in their love lives over the following years. For Rihanna, that meant high-profile relationships with billionaire Hassan Jameel and rappers Travis Scott and A$AP Rocky. She started dating Rocky in 2020. Their relationship progressed quickly, with both welcoming their first child in May 2022. The couple then welcomed their second child in August 2023.

As for Drake, he was linked to many famous celebs, including Jennifer Lopez, Hailey Bieber, and even briefly with Julia Fox. However, his most significant relationship was with former adult film star Sophie Brussaux, with whom he has a son named Adonis born in 2017. Drake also dated Johanna Leia for several months in 2021.

Also read: 6 Times Rihanna Absolutely Destroyed Critics With Savager Comebacks on Social Media

While his relationship with Rihanna may have ended, Drake has expressed his admiration for his former love. As Rihanna moves forward in her new role as a mother of two alongside A$AP Rocky, Drake can look back at his past fairy tale dreams with Rihanna and appreciate how their journeys have led them to their own versions of happiness, even if their ending didn’t quite follow his earlier vision.

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