General Dating Questions/Asking out a cashier?


Hey Ali!

There's a really cute cashier girl who started working at the supermarket near my home a few months ago. Initially, I didn't think much of it but whenever I do go there (3-4 times a week) I've noticed she does look at me and make eye contact...while I'm browsing or in another line for check out. A couple of times I've seen her looking at me while sniggering with her colleagues. Often, she'll randomly show up at the aisle I'm at for no apparent reason or she'll come over to the line I'm at and start talking to the cashier for that line (if its not too busy). Now, I realize these are good signs...but who knows might all be in my head. She does not seem overly talkative or peppy. So its hard to really say.

My basic point is...I want to ask her out . I know theres a chance she could say no but if I don't do it I'll always regret it. My problem is that I'm fine with asking someone out if I know them (through a friend or class or whatever) but I have no clue how to approach this. Should I try to make small talk with her first and ask her out the next time? or should  I just be direct and ask her if she wants to get a coffee sometime. I've considered writing down my number and handing it to her but I know its my job as a guy to get her number. For all I know, she won't call me even if she's interested.  I've also considered "running into her" outside the store after her shift ends but if she has mixed feelings it might creep her out.

Basically could you help me figure out an approach that is comfortable for her (since its her workplace and I don't want to put her on the spot). And if she says no...what should I say so its not awkward?

I'm 22 by the way and she seems around the same age.


Hi Michael,
Thanks for taking the time to write. From what you've told me, I wouldn't be surprised if this girl knows that you might be interested in someone working in there since you frequent the store 3-4 times per week. Have you considered going to her checkout line when she's working so that you can say hi and make an attempt at some small talk? That would be the first thing to do to try and get some rapport going. While it won't provide immediate results or an immediate date, it'll set the stage for you to ask her out in a few weeks.

You sound like a confident man, Michael, and I'm sure you don't need help with the small talk fodder, but this is the perfect time of year to chat about the New Year, holiday plans, etc. There are also a ton of new movies coming out around the holidays, which are often advertised on the magazine racks at many supermarket check-out counters, so you could always throw in a 'that one looks like it might be good' comment and see what her reaction is. After you've gotten a little bit more of a sense of her interest, if you'd like to ask her out, you could note that it seems like she works quite a bit and ask if she'd ever be up for grabbing a coffee or drink (or going to see that movie) when she has some free time. If she says 'yes' then great! Get her number and make a date with a specific day and time, so that it's not a wishy washy ambiguous thing that gives either of you the opportunity to push off indefinitely. If she shies away from your invitation, then you can just say that it's no problem and that you understand she's got a busy schedule. That should make it fairly comfortable for both of you - and you shouldn't feel awkward about continuing to go shopping there several times a week.

I wish you the best of luck, Michael, and hope that this girl takes you up on your offer. Just be confident, be friendly, smile when you're talking to her and I'm sure it will be difficult for this girl to turn you down. Good luck! If you have any other questions or if I can provide additional clarification, please don't hesitate to let me know.

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I can answer questions related to "the chase"--whether to be patient or more assertive. I can answer questions regarding break-ups and moving on. I can answer questions related to flirting and meeting new people as well as how to inspire them to call you.


I have much personal experience as well as often play the role of matchmaker and advice-giver with many of my friends. I took several classes related to gender relations in college, giving me a solid perspective on communication between couples and what it means.

My writing has appeared on a website and various anthologies.

Graduated with a BA from Villanova University.

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