Celebrity A Timeline of Drake's Romances On-Screen and IRL By Jane Asher Jane Asher Jane Asher is a New York-based writer, editor, and social media manager covering all things beauty, fashion, and celebrity. She was previously the Assistant Social Media Editor at InStyle. InStyle's editorial guidelines Updated on December 28, 2016 @ 08:00PM Pin Share Tweet Email Trending Videos Photo: Gabe Ginsberg/Getty Drake has had a long history of romances, from his famous on-again-off-again saga with Rihanna, to his even more famous (and more recent) Instagram with Jennifer Lopez, which she reposted on her own account, basically confirming their dating (or at least hooking up) status. Then of course, there were his Degrassi days—Jimmy and Ashley forever!—not to mention the on-screen girls from his music videos. And yes, we're including that famous Nicki Minaj lap dance from her "Anaconda" video, which reportedly sparked his now-famous feud with Meek Mill, Minaj's on-again-off-again boyfriend, although she and Drake were never officially dating. We've put together a brief timeline of Drake's lovers, both on and off-screen, just to take a peek inside the complicated dating life of the rapper. We're sure there's much more to him than meets the eye, as Drake loves to keep his private life private, entertaining us only with a cryptic Tweet or Instagram photo here and there. VIDEO: Watch Drake Jam Out to Taylor Swift's "Bad Blood" at the Gym Scroll down below to take a look! 01 of 09 Ashley Kerwin On Degrassi: The Next Generation, 2001-2009 Alamy Stock Photo As Jimmy Brooks on Degrassi, Drake's character dated Ashley Kerwin (portrayed by Melissa McIntyre, shown on the bottom left) on-again and off-again throughout eight seasons of the show. 02 of 09 Rihanna, 2010 Courtesy The duo collaborated on the song and music video, "What's My Name," for Rihanna's album Loud back in 2010. The pair were linked romantically not just on the screen, but in real life during that time as well. Plus their hot and heavy performance of the song at the 53rd Grammy Awards pretty much confirmed the IRL relationship, even if they never officially did. 03 of 09 Rihanna, 2012 Courtesy Drake's song Take Care, featuring Rihanna was released as a single in 2012, the same year as the steamy music video, furthering rumors that the two were still together. 04 of 09 Kate Dennings, Pre-2013 Allen Berezovsky/WireImage While making a guest appearance on The Ellen Show, Drake and the host played a game of "are you dating, have you dated," and he mentioned having gone on a single date with actress Kat Dennings. "I just always had a huge crush on Kat Dennings, and she was kind enough one night to oblige me and we went out for dinner," he said. 05 of 09 Tyra Banks, Pre-2013 Paul Archuleta/FilmMagic On the same Ellen appearance where he revealed his date with Kat Dennings, he also mentioned going to Disneyland with the supermodel: "I went on a date with her one time, yeah. It was just one date. We went to Disneyland in disguise, actually, which was fun." 06 of 09 Nicki Minaj, 2014 Courtesy The duo romanced each other (or rather, Minaj romanced Drake with a steamy lap dance) in Minaj's music video for "Anaconda." They both have denied any real life romantic connection, but they make it pretty believable in the video. 07 of 09 "Work" Music Video with Rihanna, 2016 Courtesy The most recent collab from Riri and Drake was released and promoted around the time rumors started flying once more that the duo were an item, and was pretty much confirmed with their matching tattoo Instagrams, his speech (and billboard dedication) to her at the VMAs, and her Instagram, thanking him for presenting her with the Video Vanguard Award. Even though "I love you's" were exchanged, it seems the pair have broken up since then. 08 of 09 Tyra Banks, 2016 Courtesy It seems that Banks and Drake have remained friends after their Disneyland date, as she guest-starred as his girlfriend in his music video for the song, "Child's Play," getting into a nasty fight with him at The Cheesecake Factory. 09 of 09 Jennifer Lopez, 2016 jlo/instagram Sorry Rihanna-Drake shippers, it seems that he's found himself a new love in Jennifer Lopez, sparking serious romance rumors after the duo posted the same cuddling photos to Instagram in December.