Ask Alex: How do I tell my favorite cashier that I have a crush on him?


Potentially Awkward asks:

There’s this guy who works at Trader Joe’s, and I see him almost every time I shop there. He always smiles at me, he’s always friendly, he makes small talk, etc. Sometimes the small talk seems sort of flirty. This leads me to two questions for you:

  1. How can I tell whether he’s actually flirting with me or just being friendly as part of good customer service? I feel so lame for not being able to decipher this on my own.
  2. How can I convey to him, without appearing totally creepy, that I’d like to get to know him better? It doesn’t seem like something I should just blurt out while he’s ringing up my six-pack of Stockyard Stout.

Caveat: I’m not sure if this makes a difference in how you’ll answer the question, but I’m gay. I’m 99% sure that he’s gay too, but there’s always the chance that my gaydar is wrong. I guess that could potentially increase the Awkward Factor by about 1000%.

First of all, I don’t think that you should feel lame for not being able to tell the difference between solid customer service and flirting. Flirting is not a standardized element and there is no science applicable to better understanding it. I imagine that what you are picking up either is or feels a lot like chemistry, which is inexact and itself not always easy to identify. More on that shortly.

It is also important to consider—and by mentioning this I don’t mean to scare you off from doing what is best for you—that people in the service industry are asked out all the time. Often, hospitality is confused for flirtation, and those who are particularly hospitable are often confused for being particularly flirtatious.

But sometimes flirting and flirting and chemistry is chemistry. Should you feel that there is actual chemistry, make your move.

I have approached and dated people in exactly the circumstance you describe and it has gone very well. I have also approached people out in this situation and been turned down because I—as I suggested happens often—confused hospitality for flirtation. My follow-up visits to those establishments were awkward for the next couple of times I visited, but that faded over a relatively short amount of time. I have also been on the receiving end of the invitation while working in hospitality, have both accepted and declined, and don’t have much negative to report.

If you believe there is something between you two, speak up. I have no regrets in my life and am happy that I ended up where I am. I would not change a thing. There have been a few occasions, though, where I have run into people I used to have an  interest in that I never acted on only to find that they felt the same way. Why didn’t I act, I wonder? Again, no regrets but sometimes I am curious about why it took me so long to become adventurous in the same way I am encouraging you to be.

Through all of that trial and error, though, I have become a much more direct person. I am not someone who does well with passive aggression and so I tend to speak my mind. In being this way, I am rarely conflicted about what was or what was not said. In this case, I might say to the cashier, “I don’t mean to be too forward, and I fear that this could make things awkward in the immediate future, but would you be interested in grabbing a drink sometime soon?” This way you are at once disarming and direct. If he is interested, high five! If not, you have acknowledged any potential fallout up front so as to minimize any weirdness afterward. If you do so with poise, I don’t think that asking him this while he rings up your stout is out of hand.

About the caveat of being you gay, I don’t know that it changes much outside of the worry that perhaps the object of your affection is not himself gay and this could lead to an awkward response. If it does goes down this path for whatever reason, and I can’t imagine that it would, tell him what my father used to tell people who rubbed him the wrong way:

“Go shit in your goddamned hat.”

Alex Steed

About Alex Steed

Alex Steed has written about and engaged in politics since he was an insufferable teenager. He has run for the Statehouse and produced a successful web series. He now runs a content firm called Knack Factory with two guys who are a lot more talented than himself.