The one place I have mixed feelings about asking a girl out is as a customer because of the dynamic associated with her being an employee.

How many of you have done it? Does it go good or bad? I broached the issue with one once who wasn’t into it but I get a nagging desire to try it again.

4 comments

  1. 9 times out of 10, the answer is don’t do it – Best-case-senario? You hit it off well.

    Worst case? Anything from awkward interactions at work afterwards to a harrasment complaint.

  4. I think if done respectfully it could work. However you need to read the room first. Is she talking to you a lot more? Do you have inside jokes? Lots of smiling, laughing, playful touching? If yes, might be worth a shot to casually ask her to get coffee.

    However if she’s just your run of the mill Starbucks cashier or something who doesn’t engage with you much outside the classic customer/employee back & forth, then best to leave her be.

    If you find yourself unsure if she’s flirting, maybe err on the side of caution. You don’t want to be the creepy customer. However, if you feel a vibe, just try it. If she says no, LISTEN TO THAT, and don’t try again.

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