Rihanna and Drake grabbed dinner at Nobu after staying together the night of the 2016 MTV VMAs. People even began speculating Rih wore the rapper's shirt for their date night out.
Not only did Drake present the Video Vanguard Award to Rihanna at the 2016 MTV VMAs, he also professed his love for her, telling the crowd he's been in love with her since he was 22.
Ahead of her Video Vanguard Award night at the 2016 MTV VMAs, Drake bought a Billboard to honor his lady.
Drizzy brought Rihanna out on-stage at his 7th Annual OVO Fest Concert in August 2016.
Rihanna and Drake were spotted exiting Tape club after partying together for the fourth night in a row in London in July. A source told E! News at the time that the couple had officially started dating again.
Rihanna was seen partying at Tramp nightclub after flying back from Manchester on a private jet following her Anti tour stop at Old Trafford where Drake joined her on stage in June 2016.
The rapper and the Barbadian singer performed together several times throughout the spring and summer of 2016 as Rihanna's Anti World Tour continued.
In May 2016, Drake was spotted at Rihanna's concert after-party held at The Nice Guy in West Hollywood.
The pair heated up the 2016 BRIT Awards with their sexy rendition of "Work" at the end of February 2016. Rih twerked on the rapper as they performed their collaboration.
Although 2015 was a quiet year for Drake and Rihanna (the rapper was reportedly dating Serena Williams while Rih was busy working on her album), they revamped the rumor mill in February 2016 after RiRi released her collab and sexy video for "Work" with Drizzy.
Things appeared to have slowed down between the couple by the end of summer 2014. In fact, when Drake performed "Days in the East" at the OVO Festival in his native Toronto in August 2014, pictures of Rihanna with devil imagery flashed behind him onstage.
In April 2014, Drake and Rihanna were photographed hugging each other at a Clippers game in Los Angeles.
The bad gal and her on-again/off-again beau were spotted holding hands in London after leaving Tramps nightclub. They had been spotted dining out together three nights in a row during their March 2014 rekindling.
The pair got together on-stage during Drake's Paris concert stop in February 2014, showcasing their love for the audience.
Drake and Rihanna were spotted leaving Hooray Henry's Nightclub just seconds apart in West Hollywood, CA in February 2014.
Rih got back together with Chris Brown officially in September 2012, but they split for good in May 2013. She was spotted hanging out with Drake again in November 2013 at one of her concert after-parties in Los Angeles, and it appeared they began rekindling their old flame.
Despite seemingly rekindling with Chris Brown, Rihanna and Drake released another song together off his 2011 album, Take Care.
In the song, Drizzy raps, "Pushing me away so I give her space/ Dealing with a heart that I didn't break/ I'll be there for you, I will care for you/ I keep thinking you just don't know."
The romance rumors continued between the two when they collaborated for the first time on "What's My Name" in 2010. They later performed the hit at the 2011 Grammy Awards.
The pair attended a party after one of Drake's concerts at Greenhouse on September 28, 2010 in New York City.
The couple first sparked romance rumors in 2009 when they were reportedly spotted making out at Lucky Strike Bowling Lanes & Lounge. Drake even mentioned the night in his "Fireworks" song, writing, "I could tell it wasn't love, I just thought you'd f--k with me/ Who could've predicted Lucky Strikes would have you stuck with me?/ What happened between us that night it always seems to trouble me."