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Taylor Swift & Drake’s Friendship Timeline, From Competing Chart Toppers To Supportive Besties

As 2023 winds down, Taylor Swift’s stellar career shows no signs of slowing down. Not only has her music continued to top the charts, but she’s also been the topic of many people’s conversations thanks to her blossoming romance with Travis Kelce. But her popularity doesn’t stop there. On Nov. 16, Drake gave a shoutout to Swift in his new song. In his freshly released single “Red Button,” part of his new Scary Hours 3 project, Drake paid a unique tribute to Swift in the lyrics, “Taylor Swift the only one I truly admire. Made me reconsider my album’s debut, took it higher. For the rest, it’s like they never even touched the mic.” 

Drake’s latest shoutout to Swift is a continuation of a long-standing friendship between the two musicians. 

Over the years, Drake and Swift have frequently engaged in a friendly rivalry for the top position on the pop charts, a trend that was particularly evident in 2022. Swift’s album Midnights, released on October 21, took the charts by storm, selling 1.5 million album equivalents in its first week. Not wanting any competition, Drake and 21 Savage postponed the release of their joint album, Her Loss, from its planned October 28 debut to November 4. Although Swift’s single “Anti-Hero” from Midnights maintained the no. one spot on the Billboard Hot 100, Her Loss ultimately overtook Midnights on the album charts following its release. Despite their chart competition, the relationship between Swift and Drake is far from a rivalry.

Drake and Taylor Swift Are Seen together at the 2013 MTV VMAs

The friendship between Drake and Taylor Swift notably began in 2013 when they met face-to-face for the first time at that year’s MTV Video Music Awards in Brooklyn, New York. During the event, Swift and Drake were seen in high spirits, sharing several photos together while celebrating their respective successes. Swift secured the Best Female Video award for “I Knew You Were Trouble,” while Drake delivered performances of two major hits, “Hold On, We’re Going Home” and “Started From the Bottom.”

Birthday Besties

In 2016, Taylor Swift was spotted at Drake’s 30th birthday party, a gathering filled with other celebrities. Drake’s social media post from the party – a mysterious photo of him and Swift shot from behind – sparked excitement and speculation among fans. This intriguing image led Swifties and Drake stans to wonder about a potential collaboration.  

Taylor Swift’s Jacket Features A Drake Pin

In 2019, Taylor Swift subtly showed her appreciation for Drake, a move that was quickly picked up by her fans. On the cover of Entertainment Weekly, she donned a denim jacket adorned with pins, including one of Drake, fueling speculation about a possible collaboration in her upcoming album Lover. Yet, when Lover dropped, it featured no tracks with Drake. The real clue lay in her lyrics, especially in “I Forgot That You Existed,” where she sings, “I couldn’t get away from you / In my feelings more than Drake, so yeah,” a line echoing Drake’s own “In My Feelings.”

Drake’s Instagram Throwback Ignites Swift Collaboration Buzz

Last April, Drake surprised fans with an Instagram post featuring a throwback photo with Swift, believed to be from his 2016 birthday bash. The caption read, “They too soft to understand the meaning of hard work,” which only heightened the intrigue. 

Drake’s recent shoutout to Swift has Swifties buzzing again, eagerly anticipating a collaboration that’s been hinted at but has yet to come to fruition. Until this happens, we’ll keep our fingers crossed that these two will one day hit the studio and release a song together.

Come on, Drake and Taylor, we’re ready for that epic collab!

Milan Parker

Agnes Scott '24

Milan Parker is an Entertainment and Culture writer for Her Campus national, where she covers the latest news in pop culture. She is a senior at Agnes Scott College pursuing a major in Africana Studies. She is also a member of Her Campus's Election Team, interviewing 2024 Electoral Candidates running for the House of Representatives and Congress. Outside of writing for Her Campus, Milan spends her time writing poetry, some which have been published in Alloy Magazine at Emory University. Currently, she plans to release a written mini-series of her favorite 2000s childhood memories, titled "Confessions of a Y2K Kid". When she is not on the lookout for the next big story, Milan enjoys online shopping, cozying up in libraries, discovering new music, spending time in nature, and taking to the streets on her inline skates. To this day, she's still perfecting the perfect skate routine.