Drake Was Sooo in His Feelings Over Rihanna at the VMAs: Was It Sweet or Awkward?

The first time Drake met Robyn Rihanna Fenty was 2005 — and for the rapper, it was love at first sight.

“She’s someone I’ve been in love with since I was 22 years old,” Drake told the crowd as he presented Rihanna with the Michael Jackson Video Vanguard Award at the MTV Video Music Awards on Sunday.

The audience erupted, and viewers at home immediately tweeted their suspicions that Drake was about to propose to his rumored girlfriend.

Until he went in for the kiss.

After gushing about her work ethic, her personality, and her ability to always keep it real, Drake tried to seal the deal with a kiss that was swiftly curved by Rihanna. As the “Controlla” rapper leaned in for the heavily anticipated kiss, it appeared Rihanna jolted away and caused Drake to narrowly miss her lips.

The doting speech may not have led to the steamy smooch fans were hoping for, but the awkward “kiss” doesn’t take away from Drake’s heartfelt words about the “Needed Me” singer.

“She was shooting a music video at a restaurant called Avocado in Toronto,” Drake recalled. “The song was ‘Pon de Replay,’ and the director of the video was Little X. I was introduced to her as a kid who played background music at the restaurant as people ate their dinner. It’s hard to believe that 11 years later all three of us would come together for a visual for a song called ‘Work.’ Today, the world knows Little X as Director X. They know me as Drake and not the kid singing while you order pasta. But 11 years later, we still all know Rihanna as the one and only Rihanna.”

He continued: “Captivating from day one, the iconic being that is Rihanna was already at a place where most artists only dream of going. For them, that’s often the peak, but for her, that was a starting point, and she has kept ascending to an untouchable level ever since. When it comes to music, she relentlessly takes over the charts with every release. When it comes to performance, they swarm in masses just to be in her presence, obviously. And when it comes to fashion and style, she makes it seem so effortless until you try to do it yourself, which is when it gets a little awkward.”

“What’s most impressive isn’t the endless list of stats, awards and accomplishments. What’s most impressive is the person. Some artists need to play a character to achieve success. Some need to downplay their own natural instincts to blend in. She succeeds by doing something that no one in this music industry does, which is being herself. This woman has surpassed all competition while still being the same girl from Barbados, surrounded by the same friends, speaking with the same accent and never missing a Crop Over unless it’s to come perform at OVO Fest.”

The earnest awkwardness continued backstage as the two held hands and Drake tripped on Rihanna’s train.

Drake has never been shy about his adulation for Rihanna. Just this week, Drake purchased an entire billboard to congratulate the singer on her upcoming award.

Rihanna captured the billboard in an Instagram shot, playfully captioning the post, “When he extra.”

Even though the lavish billboard wasn’t enough to prevent Drake from being curved on stage, it turns out his relentlessness at least earned him a kiss at the afterparty as the couple cozily hit the town together. Drake posted this late-night selfie with Rihanna mere hours after declaring his love for her:

It’s safe to say the pair’s cryptic flirtations certainly keep us on our toes — even though it’s painfully awkward to watch!