General Dating Questions/Asking out a cashier?


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 queue to pay. 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.

I want to ask her out . I'm not mortified of rejection but I have zero experience asking someone I barely know for their number. Should I be direct with her and ask her to go for a coffee? Should I give her my number? Should I make small talk a few times and then ask her out or should I just ask her out right away? I've thought of running into her outside the store after her shift ends but that seems very creepy.

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?  It all feels too difficult because I've seen her SO OFTEN and yet I can't just ask for her number. I'll have to make some kind of small talk, introduce myself AND ask for her number on top of that. I'm basically in need of help regarding how I should phrase it.  I think I might have a decent chance...but since I barely know her I want to be direct but not too aggressive.

I'm 22 by the way.

Any advice? Thanks!!

Hello Michael!

No! Do NOT ask her to go have coffee. Do NOT give her your number. Do NOT stalk her after work! There are far better ways to approach her. These are not only incredibly weak, but will hurt - not help - your chances.

I teach a number of "approach methods" but the easiest is called the "context approach". "Context" is actually a very simple process of answering a question: "what do she [your target - like this cashier] and I have in common at this place, at this time, in this situation?"

The answer to that question is your "context" for approaching her.

For some guys that seems daunting - mostly because they are just too lazy! As an exercise with my students, we'll go some place where people are and I'll have them come up with 101 individual points of context for the people there. That seems like a lot but in fact, it's incredibly easy when you get started. You have many built-in points of context like the fact you're both in the same city or store, the weather, that you both speak English and that neither of you is a zombie (don't laugh - it's context!)

The point of this exercise is to get the mind thinking. You don't usually think this way in your daily, waking life but if you want to be successful approaching people you need to learn how to do this - and just how easy it is.

So, back to the cashier: what do context do you share with her? I could come up with a TON of them without even knowing either of you. You both are in the same store, in the same city in the same state in the same country for example. You both use the store; albeit for different purposes (you shop, she works). You both have families and travel and have dreams and goals and wants and needs, etc., etc. All of these are examples you can use to build an approach.

Before I get too far let me explain a key point about approaching someone. You're never going to make someone fall in love with you just because you approach them. Yes, I know that SOUNDS obvious but you'd be shocked at how many people actually think you have to do this! They go back to the "Top Gun" example when Tom Cruise starts a mock-fight in a bar and then starts singing to a girl he wants to meet. That's ridiculous - and completely unnecessary!

All you're trying to do with the approach is break the ice - nothing more. By "breaking the ice" what I'm saying is "create interest" - and even the smallest interest will do! Since you're not going to be able to make her fall in love with you (and thus, do all your work for you!) all you can do is focus on that interest. Once you have "context" the "interest" is guaranteed!

See how easy that is?

One of the things I don't do is to postulate on all the thousands upon thousands of possible times and ways you might approach someone. There are just too many of them and you're just about as likely to be in one with her as any other. However, there *is* one situation you already know you have: she's working and you're shopping. What about using that as your reason (context) to approach her? You can easily ask for her help in finding something, getting the layout of the store, checking pricing, etc., etc., etc.

Any of these allow you to break the ice and start talking to her. Once you've done that the "interest" is already there! You have something in common. The next step is to work on building some minor rapport and connection and finally to close for what you want.

Building rapport and connection is a much larger discussion. I deal with that in great depth in my books, "Being a Man in a Woman's World" - and I strongly encourage you to read them. However, if you just build some connection with her - anything will do - it'll lead to the final step.

Within minutes you should be able to "close". Just say, "You seem like a fun girl but I don't want to get you into trouble here at work. We should get together sometime when you're not working. Here, let me get your number and I'll call you sometime". then, you pull out your phone and collect the digits.

Then, you disengage, let her get back to work and you go back to shopping knowing you can call her in a few days to set up a REAL date. No coffee (that's for business meetings) no movies (you need "face time") etc. Go do something fun.

Best regards...

Dr. Dennis W. Neder
CEO/Executive Producer
BAM! Productions
Remington Publications
Producers: "BAM! TV" and “Love and Sex”
Publishers: "Being a Man in a Woman's World I, II & III”

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Dr. Dennis W. Neder


I'm able to answer any sort of question related to the approach, meeting people, dating, sex, relationships, break-ups, non-legal marriage and divorce questions, and anything in between. I've helped over 30,000 people with their individual issues. IMPORTANT: Please, PLEASE don't ask me, "what was he thinking..." or "why did he say..." types of questions! I DO NOT READ MINDS! There are 1,001 reasons why someone does what they do, says what they say or thinks what they think. If you *REALLY* want to know what they were thinking, saying or why they were acting that way - go ask them! Be sure to check out my FAQ's on my website at: You can email me directly at:


I am the author of the books "Being a Man in a Woman`s World I & II" and "1001 Places and Techniques to Meet Great Women" and 11 others. I`ve spent the last 20 years studying the art and science of every aspect of relationships, and have answered over 30,000 letters from readers all over the world. My main focus is men`s relationships with women, but I also have many female readers and answer questions for them regularly as well.

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