new yorker covers - valentines day 30

New Yorker Covers That Capture Valentine’s Day Romance

Love, Laughter, and Candy Hearts

Ah, Valentine’s Day—the holiday of heart-shaped candies, those awkwardly sweet “Will you be mine?” notes passed around in class, and the giddy excitement of classmates who had no idea what romantic love meant (I still don’t). I still remember those “Check Yes or No” notes, the sheer drama of it all, and how seriously we took those fleeting crushes.

new yorker covers - valentines day_23

Confession time: as I’ve gotten older, I’ve admittedly soured a bit on the whole Valentine’s romance thing. Let’s face it, the holiday can feel a little… Hallmark-y. But despite that, there’s something endlessly entertaining about watching people dive headfirst into the rituals of love—overpriced dinners, extravagant gestures, and all. And while my feelings on romance may have shifted, I still enjoy seeing the ways artists depict the hilarity, peril, and sweetness that come with love.

That’s what makes the New Yorker Valentine’s Day covers so fascinating. These illustrations reflect the ups, downs, and sideways twists of human connection, told with humor, heart, and a perfect pinch of cynicism.

New Yorker Covers: A Timeless Valentine’s Day Tradition

For nearly a century, The New Yorker has delighted readers with covers that capture the spirit of the times, and Valentine’s Day is no exception. These covers highlight the many shades of love—playful, poignant, awkward, and everything in between. Whether it’s a classic depiction of romance or a clever twist on modern relationships, the artwork offers a thoughtful reflection of how we celebrate (and sometimes fumble through) this holiday of the heart.

Valentine’s Day is often steeped in traditions like exchanging cards, giving roses, or sharing chocolates, but The New Yorker takes it further, spotlighting the humor, quirks, and surprises that make love such a universally relatable experience. Each cover, in its own way, invites us to laugh, smile, or reflect on the moments that make this holiday so special.

new yorker covers - valentines day_21
February 18, 1991. Artist: Ronald Searle (Source New Yorker Magazine)
new yorker covers - valentines day_1
February 14, 1977. Artist: William Steig (Source New Yorker Magazine)
new yorker covers - valentines day_3
February 12, 2001. Artist: Richard Mcguire (Source New Yorker Magazine)
new yorker covers - valentines day_22
February 18, 1974. Artist: Robert Weber (Source New Yorker Magazine)
new yorker covers - valentines day_5
February 14, 1994. Artist: Javier Mariscal (Source New Yorker Magazine)
new yorker covers - valentines day_6
February 13, 1932. Artist: S Liam Dunne (Source New Yorker Magazine)
new yorker covers - valentines day_7
February 12, 1949. Artist: Rea Irvin (Source New Yorker Magazine)
new yorker covers - valentines day_8
February 15, 1988. Artist: Lee Lorenz (Source New Yorker Magazine)
new yorker covers - valentines day_9
February 14, 2000. Artist: Mark Ulriksen (Source New Yorker Magazine)
new yorker covers - valentines day_10
February 12, 1972. Artist: James Stevenson (Source New Yorker Magazine)
new yorker covers - valentines day_11
February 13, 1960. Artist: Leonard Dove (Source New Yorker Magazine)
new yorker covers - valentines day_12
February 10, 1973. Artist: Charles E Martin (Source New Yorker Magazine)
new yorker covers - valentines day_13
February 14, 1970. Artist: Pierre Le-Tan (Source New Yorker Magazine)
new yorker covers - valentines day_14
February 12, 1990. Artist: Arnie Levin (Source New Yorker Magazine)
new yorker covers - valentines day_15
February 13, 1978. Artist: Robert Weber (Source New Yorker Magazine)
new yorker covers - valentines day_16
February 14, 1942. Artist: Julian De Miskey (Source New Yorker Magazine)
new yorker covers - valentines day_17
February 15, 1958. Artist: Jack Davis (Source New Yorker Magazine)
new yorker covers - valentines day_18
February 17, 1992. Artist: James Stevenson (Source New Yorker Magazine)
new yorker covers - valentines day_19
February 15, 1964. Artist: William Steig (Source New Yorker Magazine)
new yorker covers - valentines day_20
February 10, 1934. Artist: Harry Brown (Source New Yorker Magazine)

Did You Know? Fun Facts About Valentine’s Day Traditions

The OG Love Letters

Sending Valentine’s cards isn’t just a Hallmark invention. Back in the 15th century, the Duke of Orléans penned love poems to his wife while locked up in the Tower of London—talk about committing to the bit. By the 1800s, mass-produced Valentine’s cards were everywhere, becoming a staple of the holiday.

new yorker covers - valentines day_26
Hallmark will forever be in his debt

Those Little Candy Hearts? They Have a Past

You know the pastel conversation hearts with messages like “Text Me” or “LOL”? (Classic millennial vibes.) Turns out, they started in the mid-1800s, and—brace yourself—they were originally used as medical lozenges. Yup, nothing says “I love you” like a chalky throat remedy. Thankfully, they got a sweet upgrade and became the sugary Valentine’s staple we know today.

new yorker covers - valentines day_27
Cute but nasty

Cupid: The Original Love-Hate Character

Forget the chubby baby with wings—Cupid was the Loki of Roman mythology: a little chaotic, a lot mischievous, and definitely not here to make your dating life easy. Known as Eros in Greek mythology, he was more of a brooding god of desire. His rebrand as an adorable cherub? That came courtesy of the Renaissance, and honestly, it stuck. Truth be told, Cupid was kind of a little rat bastard. 

new yorker covers - valentines day_25
Just look at those beady little trouble-making eyes

Love, Art, and New Yorker Covers

Valentine’s Day might be a “Hallmark holiday,” but there’s no denying the universal pull of love—whether it’s romantic, platonic, or a complicated mix of the two. The New Yorker covers have a way of capturing this with their sharp humor, timeless illustrations, and uncanny ability to poke fun at our shared rituals of love.

From those heart-shaped candies and awkward love notes of childhood to the big gestures and quiet moments of adulthood, the journey through Valentine’s Day is anything but predictable. And that’s what makes these covers so special—they reflect all the joy, awkwardness, and hilarity that comes with matters of the heart.

So whether you’re a hopeless romantic, a Valentine’s skeptic, or somewhere in between, take a moment to appreciate the way these artists bring love to life—one cover at a time.

Related Stories

New Yorker Magazine Covers for Valentine’s Day: Art, Love, and Humor

The New Yorker Valentine’s Day covers capture the humor, charm, and chaos of love, turning the holiday into an artful celebration of all its quirks.

Unpacking the Loft Apartment Aesthetic: Design Tips and Inspiring Ideas

Loft Apartment Aesthetic: Industrial Charm Meets Modern Elegance. Explore key design elements, curated interiors, and expert tips to create a stylish and functional loft-inspired space.

NYC Apartment Entryway Table Decor: Urban Charm Meets Sophisticated Style

Turn your NYC entryway into a design moment. From bold prewar consoles to sleek loft tables, discover effortless ways to style like a true New Yorker.

  • Home
  • Art
  • Pages
  • New Yorker Magazine Covers for Valentine’s Day: Art, Love, and Humor
Scroll to Top