When you think of Peanuts holiday specials, you probably think of the Holy Trinity: the immortal A Charlie Brown Christmas (1965), the eerie It’s the Great Pumpkin, Charlie Brown (1966), and the wonderfully awkward A Charlie Brown Thanksgiving (1973). Though the Peanuts brand hasn’t helped itself by packaging unimaginative latter-day product—as well as anomalies like the well-intentioned but weird This Is America, Charlie Brown educational miniseries—in with higher-quality early shows, producers Lee Mendelson and Bill Melendez made animated specials at a furious pace for decades, and digital distribution means that whatever the holiday, it’s easy to check out the corresponding Charlie Brown adventure.

The agonies of love—more precisely, of unrequited crushes—inspired some of Charles Schulz’s most profound Peanuts comic strip sequences, and three specials inspired by those sequences are available as a $9.99 three-pack on iTunes. Be My Valentine, Charlie Brown (1975) is the marquee Valentine’s Day special; it’s followed in sequence by It’s Your First Kiss, Charlie Brown (1977) and You’re In Love, Charlie Brown (1967).

Be My Valentine centers on the Valentine’s Day party in Miss Othmar’s class. Charlie Brown, who’s never received a Valentine, is optimistic enough to bring an empty briefcase to school to carry all the Valentines he might receive. Meanwhile, Linus decides to reveal his affection for his teacher by spending all his money on a giant heart-shaped box of candy. Sally convinces herself that Linus’s gift must be for her, and in the special’s poignant climax, Sally cries alone in the classroom while Linus and his box of candy are left in a cloud of Miss Othmar’s exhaust as the teacher drives off with her boyfriend.

It’s Your First Kiss, made just two years later, marks a radical break from Peanuts tradition: the Little Red-Haired Girl is seen, and named, and kissed…by Charlie Brown! It’s not all wine and roses for ol’ Chuck, though: the bulk of the special is taken up with a big football game that pits the Peanuts gang against a team of burly, anonymous boys, and kicker Charlie Brown is blamed for losing the game when Lucy pulls the ball away as he runs up to kick for an extra point. He’s somehow been named escort for the homecoming queen, though, and when Charlie Brown gives “Heather” (the 19th most popular girl’s name of 1970) the “traditional” kiss, he blacks out and flies off into a personal fantasia, having to be informed by Linus the next day that he swept Heather off her feet.

The fourth Peanuts special overall, You’re In Love debuted the summer following the October 1966 debut of Great Pumpkin. By comparison with First Kiss, You’re In Love is a bleak affair: a parade of humiliations Charlie Brown suffers as he tries to simply introduce himself to his crush, who remains unseen and unnamed, even signing her correspondence “the Little Red Haired Girl.” You’re In Love featured the TV debut of Peppermint Patty, who hasn’t yet developed her crush on Charlie Brown; she plays misdirected matchmaker between Charlie Brown and Lucy, who have a nausea-inducing (for them) late-night rendezvous at home plate. It also marked the debut of “trumpeting”: the use of a muted trumpet to stand in for offscreen adults’ speaking voices.

Of the three, You’re In Love will be most pleasing to Peanuts purists, with a classic Vince Guaraldi jazz-trio soundtrack and an unremitting sequence of humiliations visited upon the hapless Charlie Brown—from an extended taunt delivered in song-and-dance by Lucy and Violet to a school bus that honks at the slumbering Charlie only to pull immediately away. (It also features a cameo by Schroeder’s closet full of Beethoven busts.) Still, the other two love-themed specials are worth watching—especially Be My Valentine.

The best-plotted of the three—and a great Linus special—Be My Valentine draws on some of the strip’s most iconic memes: Linus and Charlie Brown leaning on a wall, musing about life; Linus’s absurd obsession with Miss Othmar (“I never said I was in love with her! I merely said I’m very fond of the ground on which she walks”); and Linus’s technique of blowing off steam by hurling stones (here, chocolate candies) into the void, dedicating each one to a different object of his frustration. There’s even a highflown recital in the manner of the Christmastime Bible reading and the Thanksgiving history lesson, as Sally discovers that the complete text of the poem “How Do I Love Thee?” is written on a candy heart she’s handed at the class party. (Later, Linus furiously and ironically dedicates one of his discarded chocolates to Elizabeth Barrett Browning.)

Be My Valentine inspired kids across the country to send Valentines to the disappointed Charlie Brown, and it ends with an adaptation of one of Schulz’s greatest Sunday strips: when Violet tries to give Charlie Brown a used Valentine that she’s erased her name from, Schroeder indignantly rebukes her, saying that Charlie Brown has more pride than to accept a belated token that she’s only handing over to assuage her personal guilt. Charlie Brown, though, pushes Schroeder aside. “Never mind him,” says the perennial loser. “I’ll take it!”

Just two years later, Schulz decided to let Charlie Brown kiss the Little Red-Haired Girl on national TV. It was a similarly belated gesture for a character who’d by that point endured two decades of humiliation…but never mind that, he’ll take it.

– Jay Gabler

Also on The Tangential:
• The year the whole neighborhood gave Charlie Brown rocks for Halloween: An oral history
• The ten most awkward moments in A Charlie Brown Thanksgiving
• Charlie Brown’s mom admits: That Thanksgiving, I was strung out on heroin