The rapper, who has shared an on-again-off-again relationship with the Bajan beauty since 2005, made the revelation on Lebron James' HBO show titled The Shop.
During the interview, Drake didn't hesitate to mention that he certainly saw himself settling down with the Kiss It Better songstress at one point in his life.
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,' the Canadian hitmaker explained.
Drake shares that there was a time where that fairy tale was something he really wanted to make a reality.
But it seemed as if the two just couldn't make the relationship work – no matter how hard they tried.
'It looks so good on paper. By the way, I wanted that too at one time,' the Hotline Bling rapper continued.
Drake and Rihanna had rekindled their romance back in 2016, shortly after having collaborated on the singer's hit song Work, which had peaked at number two on the Billboard Hot 100.
That same year, the 31-year-old would go on to profess his love for the Fenty Beauty cosmetics entrepreneur at the MTV Video Music Awards.
'She's someone I've been in love with since I was 22 years old,' the In My Feelings star said while presenting his ex-girlfriend with the Video Vanguard Award.
'She's one of my best friends in the world. She's a living breathing legend in our industry.'
By October 2016 – just two months after his doting speech at the awards ceremony – the twosome had decided to split.
And while Rihanna and Drake were famously known for breaking up and getting back together, it seemed apparent that the two may have called it quits for good.