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"But the thing is, I was infatuated with her," Sebastian says. "I didn't want to lose her. I cried. I stayed up all night. Then in the morning, I realized I couldn't do it." He broke up with the girl the next day and never spoke to her again.
In all this turmoil, he never even considered going to his parents for advice after the breakup. "My parents are amazing," Sebastian says. "But they're not really concerned about me unless I'm really depressed ... I have a little sister who is 15, and they will pay a lot more attention to her feelings, because when a girl is sad she's not afraid to show it. And boys, when the moment comes to say something, they don't even know how."
Sebastian was devastated by the breakup. He says he felt as if he "lost his world" for a while. "My grades themselves dropped hard--very hard. I simply didn't care. Which was very uncharacteristic of me, considering it was my junior year, the most important time for college applications," he recalls. "As cliché as it sounds, this girl and what she had done to me literally consumed my thoughts."
Yet this kid, who clearly has the capacity for deep emotion, felt he had nowhere to turn after getting his heart broken. What's more, this same boy--a guy comfortable talking about being in love and having his heart broken--says he's arranged hookups with girls (ones he doesn't even know) on Facebook.
Facebook, Twitter, Snapchat, Sexting--each successive technology can introduce a new set of practical and emotional challenges for boys as well as girls. And while boys are often cast as thoughtless slobs in this arena--tossing off offensive sexts to girls as a clumsy way of flirting or passing around girls' pics that were supposed to be private--their thoughts and perceptions on the topic are more acute and subtle than one might think.
First off, if you think boys don't obsess over this stuff the way girls do, well, you'd be wrong.
"You can tell what she wants pretty much by how she texts," Dre tells me. "The dry 'Hey' is O.K. But then there's some that have the 'Heyyy' with the extra y's and the winky face [emoticon], and that means this conversation could possibly go somewhere. They're probably the hooking-up type."
Ian, who came out as gay during his sophomore year in high school, also says emoticons play a key role in sussing out a crush's potential feelings. "When I see a smiley face, it's the opening of the doorway to emotions," he says. "That first emoticon is significant. When it comes, it means something."
Brian Tian-Street, 19, whom I met at the magnet school he attended in Maryland, told me over e-mail about how he and a friend tag-teamed communication with a girl the friend had met at a dance. "He kind of wanted to continue it and thought it was easiest to bring it up via text," said Brian, who is now a sophomore at Yale. "What followed was me helping him phrase text messages letter by letter ... We discussed whether to use '...' in certain places, what to capitalize and what to not, emoticons and their placement ... Every detail was discussed, such as the time between responses. Wait at least a few minutes between responses, so as not to appear clingy or desperate." A character from Girls could hardly do a better job of picking apart linguistic minutiae.