How long did Rihanna date Drake? Complicated relationship timeline explored

Rihanna tied with Drake as the artist with the most songs with one billion streams when Don’t Stop the Music crossed the mark of one billion Spotify streams. The two singers who are at the top of the list have previously collaborated on multiple hits, including What's My Name?, Take Care, and Work. However, most fans are unaware of their exact dating history.

Rihanna and Drake reportedly dated for seven years, and their relationship was considered one of the most high-profile ones in the music industry. RiRi and Drake were first linked in May 2009, when Page Six reported spotting them at the now-closed Lucky Strike in New York City. The Page Six report came soon after Chris Brown and Rihanna split after an alleged assault.

The pair shared an on-and-off relationship for the next few years but never announced it officially. Appearing at the Angie Martinez show in November 2009, RiRi even went on to deny the dating rumors by insisting that she and Drake were still friends.

RiRi had been dating Drake for over seven years (Image via Steven Ferdman/Getty Images)

Rihanna's claims, however, were seemingly refuted as Drake confirmed the relationship rumors through his June 2010 single Fireworks. The track had fans speculating about an absence of certainty from RiRi's side, while Drake seemed to have fallen deeply for her.

“I could tell it wasn’t love, I just thought you’d f— with me/ Who could of predicted Lucky Strike would have you stuck with me/ Damn, I kept my wits about me luckily/ What happened between us that night? It always seems to trouble me,” Drizzy says in the song.

---

A look at Rihanna and Drake's relationship of over seven years

While there were talks of separation, Rihanna and Drake released the 2010 hit single What's My Name?. The chart-topping song was paired with a music video featuring the pair 'flirting at the local grocer before they went on to cozy up in an apartment.'

They took the stage together at the 2011 Grammy Awards and shared a seemingly romantic dance while performing What's My Name? The pair was next seen performing the song at the NBA All-Star Game halftime show in the same year.

In the following years of their seemingly uncertain relationship, Drake and RiRi came together several times, before seemingly parting ways in 2016.

---

Drake and Rihanna Collaborate on Take Care - November 2011

The pair was seen together for the single Take Care, which was released on November 15, 2011. Its music video featured a similar romantic engagement where the two could be seen caressing and hugging each other.

---

Drake tells Ellen that he and RiRi 'Had Their Moment' - September 2013

Drizzy appeared on The Ellen Show in September 2013 and revealed to Ellen DeGeneres that RiRi is a great girl and that they had their moment. He added that he would always have love and support for her.

---

RiRi & Drake spotted together in London - March 2014

As per a March 2014 report by the Mirror, Drizzy and Rihanna were spotted spending some quality time in London together. The pair shared the same car and went on to shop at Harrods before heading to the Mayfair restaurant for dinner.

Drizzy and RiRi pair up for the single 'Work' - February 2016

In 2016, RiRi and Drizzy paired up for the single, Work, in early 2016. Anti-tour supported the song, whose music video came with an "explicit" video. Drake shared the stage with Rihanna at the Toronto stop and the two shared a dance.

---

Drake dedicated a speech to Rihanna at the 2016 MTV VMAs

The final chapter in the on-and-off relationship was when Drake shared his feelings for Rihanna at the award speech for the 2016 MTV VMAs. Drizzy went on to share how he looked up to RiRi and that she was a legend of the music industry.

The pair was neither spotted together after the 2016 MTV VMAs nor did they collaborate on other projects. In May 2018, RiRi was asked about the current status of her relationship with Drake in a Vogue interview. She said they were neither friends nor enemies.

---

As of this writing, the Umbrella singer is in a relationship with A$ap Rocky, and the couple has two sons together. Drake, on the other hand, is not confirmed to be in a relationship with anyone. The God's Plan singer revealed to Page Six in July 2023 that he is not ready to settle down yet.