An OkCupid Blog from 2009 Foretold This Decade’s Rise of the Softboy 2023

Updated: February 5, 2023

In 2009, the only dating apps were “websites.” Though the concept of online dating had been around for a while by the end of the previous decade, people were still a bit skeptical, dipping their toes into the scene like testing out a cold swimming pool. The OkCupid blog published posts filled with bits of guidance, a lot like the advice on how to talk to people online that’s still routinely published today.

The final post of the aughts, published in September 2009, offers advice on what, exactly, to say in a first message. Most of the tips still hold up today; online dating may have changed drastically over the past 10 years, but the way humans communicate romantic interest in one another is, mostly, the same. The insights are based on an OkCupid analysis of messages sent over its own interface, so they’re basically a reflection on how people communicated in 2009, rather than pithy advice on how to score a date. Almost all of the advice is normal and applicable today: “be literate;” “bring up specific interests;” “avoid physical compliments.” But one tip stands out as a relic from a different era: “Rule 5: If you’re a guy, be self-effacing,” the post reads. “ Awkward, sorry, apologize, kinda, and probably all made male messages more successful… A lot of real-world dating advice tells men to be more confident, but apparently hemming and hawing a little works well online.” Not to hit OkCupid’s harmless blog post with too much blame, but this tip reads like the harbinger of the Softboy era that dominated much of the 2010s.

The Softboy—a fuckboy who discusses his feelings and wears beanies, essentially—wasn’t formally documented until the middle of the decade, yet his cultural predecessors were abundant at the beginning of it. One of the highest grossing rom coms in 2009 was 500 Days of Summer, which introduced us to perhaps the proto-Softboy: Tom (Joseph Gordon-Levitt), a dude who wears sweater vests, doodles on his walls, and cries when he doesn’t get the girl. Before that, The O.C. gave us Seth Cohen, a hottie who fucks but who also listens to Bright Eyes. Earlier in the aughts, a number of people fell for Jim Carrey’s portrayal of Joel in Eternal Sunshine of the Spotless Mind, a guy who was some blend of “soft” and “just depressed.”

In the 2010s, the Softboy exploded. Men seemingly realized that openly brusque behavior and using people purely for sex wasn’t working anymore, and instead opted for gentler tactics. They identified the value of using emotions as a tool to lure people in, and in using un-firm language to make themselves seem less confident and perhaps more in need of attention and validation. In 2015, the definitive essay on Softboydom was published in Medium’s Human Parts: “The Fuckboy is perplexed that you were upset when he forgot to text you for three days then sent ‘what are you up to’ at last call. The Softboy knows this behavior is selfish and cruel, though his desire to get laid can trump this. He feels shame. He does it again.” The phrase slipped into mainstream culture, and Softboys were suddenly not just on screen, but in our DMs, our Tinder inboxes, our texts, on our dates… There are so many types of Softboys that we’ve since had to divide them into subcategories, a genus-species situation for human dudes.

The inevitable backlash hit in the latter half of the decade. The explosive reaction to Kristen Roupenian’s “Cat Person” in the New Yorker revealed how common this troubling, middling type of dude was. “The whole time, he was stroking her hair and trailing light kisses down her shoulder, as if he’d forgotten that ten minutes ago he’d thrown her around as if they were in a porno and growled, ‘I always wanted to fuck a girl with nice tits’ in her ear,” Roupenian wrote. “Then, out of nowhere, he started talking about his feelings for her.” Had we all been dating this guy, maybe after matching with him on an app? Reading the 2009 OKCupid suggestion to hem and haw now, with fresh 2019 eyes—eyes that are familiar with the conceit of the Softboy, the Cat Person guy, the male feminist wolf in sheep’s clothing, and all the other bad-man species identified in the past decade—sounds blaring alarms. “Hemming and hawing” is now not quite a red, but certainly red ish, flag online; a bumbling, unconfident-seeming man isn’t necessarily a good one.

It’s hard to imagine a Softboy existing in the wild in 2020; the type has been so thoroughly excavated, no one could reasonably be one (and get away with it) in the new decade. If anyone used the “self-effacement” tip from the 2009 OkCupid post now, they’d almost certainly be identified as a certain “type,” and not necessarily a good or successful one. The sort of message the OkCupid tip advises sending—“sorry if this is awkward but you seem kinda cute, maybe we should get a drink sometime?”—would send shivers down the educated, 2019 spine. That sort of “aw shucks” equivocating made sense in the years immediately after everyone learned about pickup artistry, but now it’s a gimmick that everyone sees directly through. Maybe (definitely) there are new ones on the horizon that haven’t yet been excavated and thoroughly exposed online. The “best” way to approach a potential date is always cycling, but the desire to hide intention behind pleasing language is evergreen.

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