Few artists have aligned themselves with a holiday like Drake has with Valentine’s Day. Some dominate the summer, others claim Christmas, but Drake has spent his career crafting the soundtrack for every stage of romance—from euphoric puppy love to bitter, drawn-out endings. He captured the regret of drunken late-night voicemails on “Marvin’s Room,” the wistful hope of rekindled love on “Take Care” featuring Rihanna, and the quiet acceptance of moving on with “Feel No Ways.”
Drake has used Valentine’s Day as a marker of his career’s evolution, releasing projects that reflect his shifting perspectives on love, success, and emotional vulnerability. So Far Gone (Feb. 13, 2009) and If You’re Reading This It’s Too Late (Feb. 13, 2015) represent two sides of the same journey—one drenched in romantic hopefulness, the other jaded by experience. And with the release of $OME $EXY $ONGS 4 U on Valentine’s Day this year, Drake is once again cementing this pivotal moment in his career through a day he has subtly claimed as his own over the past 16 years.
Let’s be clear: Drake didn’t invent emo rap, but he turned it into an inescapable force upon his arrival. Mainstream hip-hop had little room for male vulnerability in romance—at least, not without the buffer of an R&B singer on the hook. Love was often framed through conquest and bravado rather than confession, but Drake blurred the lines between rapper and crooner, allowing him to explore relationships with nuance and depth. The women in his songs weren’t just flexes but reflections of lessons learned and chapters of personal evolution. “Houstatlantavegas” and “Brand New” captured late-night longing and loneliness, while “Best I Ever Had” became an anthem because of its emotional sincerity. Through these records, So Far Gone’s connection to Valentine’s Day remains undeniable and deeply embedded in modern romance.
Yet for all of his romanticism, Drake has always been most compelling when dealing with heartbreak. If You’re Reading This It’s Too Late arrived exactly six years after So Far Gone, but his world had shifted entirely. The hopeful, ambitious dreamer was gone, replaced by a man whose success became both armor and isolation. By 2015, Drake had outpaced his peers and was competing with his idols, but the success came with a heavy price—relationships suffered, trust eroded, and the world around him felt increasingly transactional.
The bookends of the album, “Legend” and “6PM In New York,” were existential reflections on his legacy. “No Tellin” delved into his paranoia, with lines like, “She invite me to the telly, keep the blade with me / When I go to check a b*tch, ain’t no tellin’” encapsulating his distrust. Then there are records like “Preach” and “Jungle,” which hint at fleeting intimacy. The emotional core of So Far Gone still lingers here, but now it feels detached—almost hollow.
Although not an inherently Valentine’s Day-oriented album, If You’re Reading This captures the other side of love: the moment it fades. It explores falling out of love, out of trust, and even out of the illusions of success. These themes continue in his later catalog—"Jaded" stings with post-breakup regret, while "Feel No Ways" traces the slow unraveling of a fading love.
Drake has always understood how to weave his music into life’s defining moments. While his grip on that emotional connection may have loosened in recent years, $ome $exy $ongs 4 U marks a return to his roots. A full R&B project with a trusted collaborator, it revisits the sounds and Toronto experiences that shaped his early career. From So Far Gone to If You’re Reading This and now $ome $exy $ongs 4 U, Drake continues to make Valentine’s Day his own. His music hasn’t defined love and heartbreak, but it has been inseparable from those emotions for over a decade. So whether you’re celebrating, reminiscing, or regretting, let Drake guide you through it. Until someone else captures every shade of romance the way he has, Valentine’s Day will belong to him.
