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How to Ask Someone out on a Date, According to Someone Who Hasn’t Done Any Such Thing in, Like, Five Years

October 24, 2013

People seem to think I’m, like, smart or something. I can only chalk this up to the eight-inch-thick glasses, because at least 75% of the time, I have no frickin’ clue what the hell they are even talking about when they ask me for guidance.

Take, for instance, the time I was directing my cousin to my dad’s old house. I asked her where she was so I could maybe use that as a starting point to help her get to the right destination by way of something other than Western Mongolia.

“I just passed a sign saying ‘Denver Art Museum, Next Exit,'” she informed me.

“We have an art museum?!?” I gasped in response.

Somehow, she managed to find her way to my dad’s house in spite of my evident lack of culture, and I later learned that the art museum was the funny-looking building across the street from my go-to library, the one I frequent at least once a week. Pay attention to your surroundings, kids.

But in spite of the fact that people must either think I’m all kinds of special or am trolling them (“There’s a Catholic church here?!?” I once asked of a fellow in Baltimore who was seeking directions to the cathedral on the hill that, I later discovered, was visible from where I was standing), they keep coming back to me anyway for advice on things I am nowhere near qualified to talk about. Windows 8 tech support, settings on the new Samsung Galaxy (I am a Fifth Order member of the Cult of Apple), how best to skin livestock using a potato peeler…I have given my solicited opinion on all of these.

So I may as continue dispensing terrible advice in an unsolicited vein. My last set of tips for going on a first date struck enough of a chord that I feel brashly qualified to talk about ways to get to the point where you’d be in the position of needing that advice, in spite of the fact that I have not asked anyone on a date in five years, nor have I been explicitly asked out on a date myself in that same length of time. 

Without further ado about nothing, then, I present: the Not Taken, Not Available Guide to (Not) Taking the First Steps in a Dance for a Chance at Romance!

1. Don’t do it. At all. Ever.

2. Okay, fine. If you really want to leave your cocoon of Netflix and Chinese delivery for some unfathomable reason, try striking up a conversation.

In some ways, this gives online dating clear advantages over that mystical, mythical in-person meet-cute that so many dreamy-eyed youths want to be able to tell their grandchildren (Pro tip: Don’t bring up the grandchildren, or children, unless you’re really turned on by people sprinting as fast as they can away from while screaming at the tops of their lungs). You can start by messaging each other about books or movies you mutually like, then progress to a flirty, “Maybe we can discuss it more over coffee ;)” from there.

But let’s say you do see your future soulmate in line at a coffeeshop or, God forbid, on public transit. In which case, I refer you back to Tip # 1. If you absolutely must proceed from there, stick with straightforward one- to two-liners that will allow you to nod and duck out if the recipient gives you the fisheye: “Hey, nice jacket! Nothing like the feel of denim on a crisp fall day!” or, “You got a Caramel Spice Latte? OMG, me too! I love [your local coffee shop’s] fall flavors, don’t you?”

3. Exchange business cards.

Assuming the recipient of your conversation attempt doesn’t stare at you like your entire head’s turned into a slimy green booger or grab their coffee and run with a tossed-off, “Sorry, running late! Had this appointment to get my toenails pulled out for weeks now and boy, is it sounding better by the minute!” you can casually whip out a business card with a suave, “If you’d like to continue this conversation, here’s where you can find me.” Assuming the target–er, recipient–doesn’t immediately use it to start flossing their back teeth, you’re probably in good.

4. Don’t be obsessive if you get a card/phone number/Facebook profile in return.

A quick, casual line–“Really enjoyed our convo earlier today!” is best followed by nothing at all from you. Trust me, your wouldbe Twu Wuv isn’t going to enjoy coming back from a conference call that lasted way too long to find a series of increasingly hysterical texts/Facebook messages/voicemails along the lines of, “You and I would have made such beautiful babies together if you’d only seen the light” (refer back to Tip # 2); “Every second that goes by forces another teardrop from my eye” (You’re a poet and you didn’t know it!); and, finally, an off-key, impromptu cover of “Against All Odds” punctuated by loud, choking sobs and the sounds of hair being ripped from its scalpy home.

5. If all else fails, Netflix and the Chinese delivery guy will always love you. Maybe too much

Admit it, you don’t really want to go out with the type of person who’ll fall for your patchy-scalped, Phil Collins-impersonatin’ self. So really, it’s all for the best that you’re all alone for the 79th consecutive Saturday night. It’s much better watching other people have interesting conversations that are only interesting because they’re written by a team of crack scriptwriters who can only imagine what a perfect first date would be like themselves, having long since resigned themselves to the greasy embrace of beef fried rice.

And if these tips do result in any of you facing a real person over real food, please be sure to video and send me the results. My Netflix queue is running perilously low.


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  1. Amber permalink

    Best advice ever, and cleverly written! I’m all about #1 and #5. And guess what? I’ve been following those particular steps for years, without even realizing they were list-worthy suggestions. I’m a dating genius… who doesn’t date!

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