How To Ask Your Local Cashier/Server Out On A Date Without Being Completely Obnoxious

Who in the universe taught you it was OK to order a woman to go on a date with you while she’s trapped behind a counter and has nowhere to go and is trying to work??

Jul 19, 2013 at 1:00pm | Leave a comment

Standing in line at my regular coffee shop today, the very blonde, very tanned man in front of me ordered two iced coffee something-or-others. He picked them up at the side counter, came back around to the cash register (budging in front of me in order to do so) and asked the woman working the counter if she’d put vanilla in the coffees.

“Yep, but we can add more if you want?”

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This does not mean I want to fuck you.

 
So the cashier hands the man his over-vanilla'd coffees. She looks at me and I start ordering. 
 
“You’re going to come out for a cold drink with me,” he says over my “double Americano ple….”
 
“I’m going to what?” she replies. 
 
“You’re going to come out for a cold drink with me and I’m going to make you laugh,” he says. 
 
She looks confused and uncomfortable.
 
“Uh, no. I will not be doing that…” she says to him irritably.
 
“Yeah no. That’s not how it works,” I say to him. 
 
He looks indignant and leaves. 
 
PLEASE. Who in the universe taught you it was OK to order a woman to go on a date with you while she’s trapped behind a counter and has nowhere to go and is trying to work??
 
Listen. I like to flirt. I am not automatically offended because someone is interested in me. Attraction or interest is not the problem. The problem is presumption, entitlement, and cornering people and making them feel uncomfortable.
 
I’ve had crushes on people (men, in my case) who work in establishments I frequent –- bars, coffee shops, the local beer and wine store, etc. 
 
I didn’t address said crushes by ordering the person who I’m buying my coffee/beer/wine from to go on a date with me in front of a long lineup of people. I recognize the fact that the man selling me my coffee/beer/wine is being nice to me because it’s his job. (Let us all learn the golden rule: smiling and engaging with you politely does not necessarily equal flirtation.)
 
I also recognize the fact that it will make that person feel uncomfortable if they are put in a position where they have to say “yes” or “no” to a date in front of their co-workers and a dozen customers. I also recognize that it’s awkward to say “no” to a customer in an industry where “the customer is always right.”
 
There are ways to go about such things that allow he or she who is behind the counter to gracefully reject you and wherein you respect the power dynamic that exists in such a situation.
Here are some of those ways: 
 
1) Leave your phone number.
 
It’s not intrusive or rude. It’s not embarrassing for you or the person behind the counter as those around are unlikely to notice such a small gesture. The crush can easily choose to call or not call. No pressure. 
 
2) Invite them to a casual social event.
 
This works best if you are regularish and have a friendly relationship with your crush behind the counter wherein you’ve been able to learn about some things and interests you might have in common.
 
“Oh you like music? I also like music. You should come to such-and-such tonight.”
 
Then the crush can choose to come or not. Again, no pressure. No one has to say “yes” or “no” on the spot. 
 
3) Go in to your local beer and wine store about three or four times a week, stare longingly into the eyes of your crush/local beer and wine merchant, make awkward small talk for nine months or so until you eventually run into them on the street and they introduce themselves.
 
This will allow you to find and stalk them on Facebook for a few more months. Continue upping your wine consumption in order to see your crush on a regular basis, coming up with elaborate plans to somehow trick them into ending up at the same party as you, at which point you will surely make out/fall in love forever.
 
After months of frustration and loving stares, run into your crush on the street, at which point they will invite you to see some band, at which point you show up (with a wingman/lady) three hours late because being late is apparently your “thing.” The object of your desire will have already gone home, but luckily you’re Facebook-stalking powers come to good use here and you send them a message: “Don’t think I’m a creep. I think we missed you tonight! Text me [leave phone number here].” Proceed to fall in love.
 
See? There are ways to go about this kind of thing without either ordering a person who is in a position of having nowhere to escape to go on a date with you, being presumptuous, or making everyone around you, including your crush, uncomfortable. It might take a year, but sometimes it’s worth the wait. 

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