Auntie SparkNotes: How Can I Talk to My Introvert Crush?

Dear Auntie,

I am an introvert, but I love people. Despite my severe social awkwardness, I’ve managed to make a bunch of friends. I stink at leading a conversation, so I either listen and ask questions, or I talk to people who are just as strange and awkward as I am and don’t mind my stuttering or abnormal choice of topic.

I am actually quite happy, and wouldn’t be writing you at all if it weren’t for this exceedingly cute boy who goes to my choir.

Said boy is an introvert as well. He listens more than he talks, he’s got a quiet voice, and he prefers to stay in the background. But that is where our similarities end. This boy is not a stuttering smiling mess when he talks to other people, he is friends with the cool kids, he’s exceptionally polite, he’s devilishly attractive, and he has no interest in me at all.

And Auntie, I have no idea how to talk to him without making an absolute fool of myself. For one thing, he’s cute, and he makes my brain go nuts. Stuttering will be inevitable. He doesn’t try to make conversation with me, and he probably won’t be interested in any of the things I have to talk about: knitting, writing, good books, food, philosophy, any type of logic puzzle, or annoying younger siblings. I could talk about choir, of course, but his mum’s the director, and besides complaining about the director and naming your favorite song I can’t really think of anything to discuss.

Tips? Advice? Help? It seems pathetic that I can’t figure out how to talk to a cute boy, but you ARE an expert on these things, and I figured it wouldn’t hurt to ask for help.

Let’s start here, Sparkler: If all you needed was to find a winning conversation topic — i.e. one centered on subject matter that the average guy is both familiar with and wildly enthusiastic about — then the answer to this question would be as simple as “Talk to him about tacos and farts!”

After all, tacos and farts are two things that just about every straight teenage boy on earth finds utterly and endlessly fascinating. (They are mysterious but simple creatures, those boys.)

The problem is, that’s not actually what you need. Because you’re not trying to have a conversation, right? You’re trying to make a connection, which is rather a different thing. And unfortunately, connection has very little to do with what you choose to talk about, and almost everything to do with the ephemeral chemistry of who you are. You could be the most witty and fascinating conversationalist on earth, with a PhD in every subject that this guy finds most interesting, and none of it would matter if he didn’t find you personally intriguing. And conversely, if he does find you intriguing, then you could come at him with the most banal conversation-starter ever (“Soooo, do you like radishes?”), and he’d happily chat with you about it until the cows come home.

And I know that probably sounds like bad news, but actually, it’s the bright side of this whole lovesick scenario: You don’t need something in particular to talk about. You just need to talk, period, and keep your fingers crossed that he returns your interest.

Of course, that brings us back to the not-so-great part where (according to you) he’s basically unaware that you exist. But that’s also another reason not to stress about discussion topics: Your first verbal contact with this guy isn’t going to be a discussion. Sparking a flirtation is all about keeping it light, and seeing if your personalities bounce off each other in an enjoyable way — which won’t happen if you launch straight into a deep-dive debate about your favorite knitting techniques or preferred brand of canned tomatoes.

So, with that in mind, here’s the actual advice portion of our column: Make it your goal not to have an extended conversation with your cute introvert crush, but just to put yourself on his radar, which is much easier, because you only need one sentence to do it. Compliment him on his hat/scarf/keychain and ask him where he got it; “accidentally” end up next to him during a rehearsal break and ask if the tenors are struggling as badly as the sops with their stagger breathing; or ask him if he was at [insert local business you frequent] last Sunday, because you could’ve sworn you saw him. (Note: This can and should be a total lie; when he says, “No, I wasn’t there,” then you say, “I’m glad I was too shy to say hello, then, because that would’ve been embarrassing” — and BOOM, you have JUST FLIRTED.)

The best part is, if you do this correctly, your conversation will likely be over after one-to-two back and forth exchanges. For instance:

You: Hey, I like your hat. Where’s it from?
Him: Wally’s Wild Emporium of Headwear.
You: Cool. I’ll have to check that out. Thanks for the tip.
You: [smiles, casually wanders off]

As you can see, this is not exactly a pressure-cooker of a conversation. But despite consisting of nothing but a bunch of low-stakes pleasantries, it opens a lot of doors. For one, it gives you a legitimate reason to talk to him again, if you want to. (“I went to the Wild Headwear Emporium this weekend. It’s crazy in there!”) For another, it breaks the ice on your First Official Interaction, which means that you can now attempt some flirting of the non-verbal variety (i.e. eye contact and a smile across the room) without coming off as a creepmobile. Plus, if the guy is interested in you, you’ve made it clear that you’re open to chatting and you’ve given him a perfect opening to approach you at a future date — or even to prolong your first conversation by engaging you in some additional surface-level banter about hats, or music, or coffee-shop dopplegangers, or whatever.

And of course, if he’s not into you, you’ll be able to tell — not because he’ll be rude, but because he’ll remain as unenthusiastic/indifferent toward you after your first interaction as he was beforehand. And in that unfortunate event, you can at least be glad you left the door open so that you can back off the same way you entered, sparing yourself all but the most minor embarrassment.

But hopefully, that won’t happen. And hopefully, your first overture will lead to many more increasingly entertaining and mutually agreeable conversations, culminating at last in a glorious denouement wherein you mash your faces together, romantical-like, forever, and ever, hallelujah, hallelujah.

Good luck, Sparkler. We’re all rooting for ya.

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