How to Accidentally Ask Someone Out: a Guide.

I have five relationship “assists.” That’s where the girl marries the next guy after breaking up with me.

There’s a fun conversation:

Friend: “Hey Ben, did you hear that {insert name} is getting married?”
Ben: “No, no I didn’t. And to think, we were just dating three months ago!”
Friend: “Yeah. She told me to tell you thanks for showing her, by contrast, what she was looking for in a man.”
Ben: “It was the least I could do. If you’ll pardon me, I have to go staple my hand to a desk, to let off some steam.”

The only thing more awkward than that conversation? Realizing that you have inadvertently asked out someone when you meant to be asking them for financial support.

It was 2004, so at least I was single at the time, but it only took me about 10 minutes into the date to realize that it was a date, and that I had done a remarkably terrible job of setting up this support appointment.

So, single male readers, here’s your chance to walk directly in my overly awkward footsteps.

I give you the Accidental Date Guide.

Step One: Lead with the date terminology.
Here’s the thing with girls: sometimes they let their emotions do an “Oregon” around their brains and their ears. By “Oregon,” of course, I mean an unnecessary trick play that, according to Kirk Herbstreit, puts them in danger of being “too cute” for a national title game. I’ve gotten rather tangled in this word-picture, but my basic point is that if you want to ask a girl out without meaning to, lead with terminology that sounds “datey.” (datish? dately?)

Here’s an example:

“Hey Mary, I’d love to grab coffee or maybe dinner with you next week and share about my ministry and how you can be financially involved.”

See, what a single girl your age who is attracted to you is going to hear is

“Hey Mary, I’d love to grab coffee or maybe dinner with you next week and WAH WAH WAAAH WAH WAAAAAH WAAH”

(once you used datesque language, your voice went all “Charlie Brown’s teacher” trombone in her mind)

By the time you finished talking, she had already mentally begun doodling her first name with your last name in the margins of her notes. No matter what you say after “I’d love to grab coffee or maybe dinner with you,” you are not being heard. She’s mentally moved on to trying to have the conversation with you about getting rid of that strange facial hair you are so proud of.

Step Two: Offer to meet at a good first date restaurant.
The thing about support raising is that often the best places to meet for a support appointment are simultaneously great first date “I want to take it slow” (and other phrases which men don’t mean) restaurants. So if you are looking to inadvertently communicate romantic intentions, Just offer to meet at a Starbucks (the world’s leading purveyor of fine coffee) at, say, 2 o’clock. Or grab lunch together at that cute little restaurant near her house. It’ll be perfect.

Step Three: Pay for the meal.
When the server (or barista) asks “Is this together?” You should definitely say yes. When I first went into ministry, the training was to always try and pay for the check on a support appointment, because that communicates that you are not looking for handouts, but partnership. I assure you, however, that is not what will be communicated when you are with a girl your age. Well, it will communicate that you want partnership, now that I mention it. Just not precisely the kind of partnership you were intending.

Those three simple steps will put you well on your way toward one of the most awkward “it’s not you, it’s me” conversations you’ve ever had.

Has something like this ever happened to you? I’d sure love to hear that I’m not alone. Comment below.

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