“How Do I Ask Out The Stranger I’ve Been DMing For Years?”

Dear Hannah,

I’ve been flirting with someone on Instagram for years even though we’ve never met. I really want to ask them out, but I have no idea where or how I should do it. Please save me from myself. Thanks!

- IG Flirter

Oh Hello IG Flirter,

Thanks for the question. Years from now, I hope we revisit this exchange with our respective offspring, bragging that whatever social connective technology they possess isn’t as hot, fun, and toxic as Instagram was. To get to your solution, IG Flirter, we need to first unpack the medium on which your relationship is built.

Here’s what I’m imagining:

Talking to this DM buddy occasionally involves sending memes you don’t fully comprehend, but pretend you do. This person allures you, but will never be a Close Friend. The bulk of your messages relies on a single running joke or a show you once remarked on in a drunken exchange. Months pass without a peep.

Then suddenly Dave on FX is renewed for a second season, and you two are back in each other’s lives again. Banter ensues, until, inevitably, one person ends the conversation with a “heart” reaction. (The equivalent of “haha cool” in the 2010s.)

How am I doing so far?

To transition out of DM purgatory, my advice is to capitalize on the kind of “send each other cool stuff” relationship you already have. Invite them to a pop-up restaurant event.

Every week I write about these special, mostly outdoor events like a gumbo night at a new Williamsburg restaurant, a Filipino pop-up at a bar in Ridgewood, or a Japanese jazz bar in Midtown that started doing outdoor shows. You can think of this weekly pop-up guide as a menu of vetted, casual date ideas to impress someone on Instagram with. Most of them happen during the daytime - which is perfect because sunlight makes everything objectively less formal. In case the date goes sour, you can both quickly adapt to platonic energy, especially because one of you may be wearing a not un-moist t-shirt and carrying a bike helmet.

The other benefit of DMing a pop-up post as a suggestion to meet in real life is that it’s an extremely specific plan, so it’s more likely to actualize than a vague “let’s hang out someday” statement. Take advantage of the fact that you’re messaging on a platform that already makes it easy to send a post without tons of context. All you have to do is pick one of the pop-ups (like free ice cream in Clinton Hill or an art show at a Southern restaurant) and follow up with something to the effect of, “This looks great.” Naturally, they’ll agree, think highly of you for finding something exciting and ethereal, and then you can make your move.

IG Flirter, we’re talking about Instagram, after all. A place where everything appears peachier than it really is. So taking the next step offline is probably going to feel scary. Remind yourself that this gesture is, actually, relatively low risk. You two likely know each other in a hyper-specific DM context rather than regular life. What’s the worst response possible? They say “uh, no thanks?” and then you stop DMing? Meh. There are plenty of other people on Instagram to flirt with. And Dave isn’t that good of a show anyway.

You got this.