How to Hit On a Woman at Her Place of Employment

It looks like you’re a cool, hip fella who enjoys such cool, hip activities as “occasionally leaving your house” and “interacting with other people.” Congrats! While involved in one such activity, you’ve come across an attractive young woman who happens to be working, perhaps at a restaurant or event venue. You would like to get to know her better. Here’s how to go about that.

Step 1: Don’t.

But—

No.

But—

You’re going to do it anyway, aren’t you.

Probably.

Fine.

Step 2: Assess the woman’s age. Is it probably within five years of yours? If yes, continue to Step 3. If no, consider trying your luck at the bar or on Tinder.

But—

Not negotiable.

Step 3: Without getting in the way of her doing her job, try talking to her. Ask her a series of polite, non-invasive questions like:

  • What is your name?
  • How are you?
  • How long have you worked here?
  • Where are you from?
  • When and why did you move here?
"No, please, go on. I'm very interested in this conversation." The Waitress, John Robert Dicksee

“No, please, go on. I’m very interested in this conversation.”
The Waitress, John Robert Dicksee

Closely observe how she interacts with you. Is she keeping her answers as short as she can without seeming rude? Is she changing the subject whenever you try to talk about her personal life? Is she looking off in random directions as if hoping that another customer will need her assistance or that her boss will appear? Is she checking her phone even though there’s nothing on it?

All of these are signs that she’s really not interested. Thank her for her time and then make your exit.

But dude, she’s totally into me.

What makes you think that?

Look at how nice she’s being. She’s definitely flirting with me.

Have you considered that she is literally being paid to be nice to you right now?

But she’s joking with me and maintaining eye contact and being super friendly.

Wow! Sounds like she’s pretty great at her job!

Just tell me the next step already.

Step 4: Don’t talk about sex.

But I love talking about sex!

I’m truly surprised to hear that. You seem like a pretty reserved guy with a good understanding of boundaries.

Hey, thanks!

Any time. To continue: Don’t talk about sex. Don’t suggestively circle around the topic. Don’t talk about the nude paintings in the gallery behind you with a wink-wink-nudge-nudge sort of tone. Don’t talk about how cool your leather jacket is and then suggest that she would look good in it, and that she would look especially good wearing nothing except for your cool leather jacket. Just don’t.

Step 5: Make your move. Be polite about it. Here’s a script for you: “Hey, I really enjoyed talking to you. I’d like to see you again sometime.” Then ask for her number or, better yet, give her yours. You are a professional man who has his life in order, right? Then you should have at least one business card on you somewhere. Offer it to her.

Don’t invite her to come out with you after she gets off work. Don’t try to make plans then and there. If she doesn’t want to give you her number, then don’t push the issue. If she does, or if she takes your card, then your work here is done.

What next?

Step 6: Leave.

That’s it?

Well, yeah. She’s working, remember? She probably has other things she’s supposed to be doing right now, and you’ve accomplished what you set out to do. Thank her for talking with you, say you hope you’ll hear from her soon, and leave.

Can I hug her?

No.

Can I pat her on the back in a casual-yet-intimate way, as if she were one of my bros who I also find incredibly attractive?

No.

Can I—

NO. You can shake her hand. That’s it. No touching. You don’t just go around touching random women, got it? That’s not okay. Why do guys think this is okay? It’s not okay.

If you’ve followed these steps correctly, you’ve successfully hit on a woman at her place of employment without coming across as a total creeper. Congratulations! I wish you the best of luck in all of your questionably-appropriate dating endeavors.

Thanks for the help! Say, would you like to—

No.

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