I’ve always liked Valentine’s Day, and believe men who dismiss it as commercialised nonsense are joyless tightwads. My enthusiasm dates back to primary school. My teacher made us cut scraps of shiny red paper into heart shapes, glue them to flimsy cards, and write messages inside to our mums – although I remember wanting to give my card to a girl named Demelza.

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Ernest Hemingway said he had to be in love to be able to write. When I was a teenager in the 1990s, I had to be in love to go to school. My love was usually unrequited, so Valentine’s Day offered an annual shot at redemption. In year 9, I loved Tammy, so I wrote a haiku inside a Valentine’s card and placed it on her desk, along with a Terry’s Chocolate Orange. “Thanks,” said Tammy. I said I loved her. “You don’t know what love is,” she said, and went to maths.

I sent more Valentine’s over the years and felt sorry for myself when they got me nowhere. “Why won’t she like me?” I wailed, alone in my room, Radiohead’s Pablo Honey playing on repeat. At university, after reading Chaucer’s The Knight’s Tale, in which two men compete to decide who will marry a princess without ever really consulting her, I posted a Valentine’s card to Becky, with whom I’d been besotted in sixth form. This was Chaucerian courtly love, I told myself, but Becky disagreed and said getting my card out of the blue was scary. I’d never considered that it might be unpleasant to receive my unwanted attention.

I take responsibility for my mistakes but I also wonder, in retrospect, if there was something in the cultural water of the 90s which encouraged boys such as me to think girls should like us. Last year, in an article for the New Yorker, the actor Molly Ringwald discussed the 1985 film The Breakfast Club, in which she plays Claire, who is sexually harassed – at the same time as being called shallow and pathetic – by the film’s slacker anti-hero, Bender. “It’s rejection that inspires his vitriol,” Ringwald wrote. “He never apologises for any of it, but nevertheless he gets the girl in the end.”

Facebook Twitter Pinterest ‘Nirvana were progressive in important ways, but there was also a sense of grievance about Kurt Cobain that encouraged a form of male entitlement that was arguably no less toxic than the machismo he rejected.’ Photograph: Frank Micelotta/Getty Images

By the 90s, young men like Bender were everywhere, as the popularity of Nirvana brought outsider schtick to the masses. Nirvana were progressive in important ways, speaking out against homophobia and sexism and critiquing masculinity in songs like Been a Son. But there was also a sense of grievance about Kurt Cobain that encouraged a form of male entitlement that was subtler, but arguably no less toxic, than the machismo he rejected. Today it seems ridiculous to think that long after he had been hailed as the voice of his generation, Cobain was harbouring grudges against the popular crowd at his high school.

Nirvana’s music remains influential, as does the quintessential 90s sitcom Friends, even though the problematic behaviour of Ross Geller has been enumerated. Ross is obsessed with Rachel, his younger sister’s friend, jealous of her male colleagues, and feels threatened when she’s successful. But Ross is an educated, sensitive guy, so Rachel should like him, surely?

Perhaps the writer David Foster Wallace, a 90s figure in outlook and image, thought like this. You’d never guess from the stories in Brief Interviews with Hideous Men (1999), which examine male attitudes to women. Recently, though, the author Mary Karr described how Wallace terrorised her after they stopped dating. Did being able to write thoughtfully about misogyny mean Wallace assumed there was no need to check his own behaviour?

In 2018, some male commentators claimed #MeToo was taking the fun out of Valentine’s Day – this is nonsense. As the writer Jaclyn Friedman said in reply: “The only people for whom #MeToo is making the world less sexy are abusive men and their enablers.”

If you are sending a Valentine’s card, just make it clear it’s from you, as anonymity is too steeped in the idea of romance as pursuit to be appropriate now. Think carefully before sending one to a colleague; many of us meet our partner at work, but if you get this wrong it’s a recipe for awkwardness. Do not send a Valentine’s to somebody who you ultimately know is not into you (in my heart of hearts, I knew mine were unwelcome). Finally, come up with a better gift than a chocolate orange. And, if it still doesn’t work out, move on without feeling sorry for yourself.

• Max Liu is a freelance writer