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Approach a Woman
Who Works In A Grocery Store


How to approach a woman who is a cashier...

Dear WWWFM,

There is a woman that I see about once a week in a grocery store. Every time that I am there we are always making eye contact. I have only talked to her briefly once, because she always has a line of customers and I don't want to talk to her when everybody is around.

My question is, what would you recommend as a good approach to her? Also, I would like to pay her compliments that I really believe to be true, but I don't want to come off the wrong way. I am a good looking, intelligent, confident man, who is genuine and sincere, but that is hard to show to a complete stranger.

Any advice? Thanks.

Thanks for writing. Well, it sounds like she is a cashier. So I can see your dilemma. Hmm. Are there any times during store hours when it’s not so busy, when you would have an opportunity to stand there for a few minutes without having to worry that someone else will be right behind you? You might have to go in at different times to find out when it’s slow, like maybe when the store first opens. Then, if you do have a few minutes to chat, look her in the eye, be sincere, and just be yourself.

If I were in her situation, I would appreciate it if a man were straightforward and not trying to impress me with a clever one-liner. A nice smile is important and eye contact too, which you mentioned. If you compliment her in a sincere way, I don’t see how you can go wrong. Good things to compliment might be her hair, her clothes, her eyes, her smile, or even her skill as a cashier. If she’s wearing a name tag and she has an interesting name, comment on that.

If you’re feeling really bold, you might just come out and say, “Would you like to have a cup of coffee with me sometime?” If there’s no one else in line when you do it, and she says yes, then you could ask for her phone number or email address. If someone shows up as you’re asking her, have your business card ready to hand to her and ask her to call you.

Maybe you want to chat with her a few more times before actually asking her out. If so, consider learning a good joke or two and then tell it to her, the kind of joke where you ask something like, “How many plumbers does it take to screw in a light bulb, etc.” so she has to answer you. Humor is a great way to break the ice and women really appreciate a good sense of humor in a man. Or maybe tell some little interesting bit of trivia when you hand her your money like, “Did you know paper money is actually made from a blend of 25% cotton and 75% linen and that they fold a bill 8000 times to test it?” Even if you don’t normally tell jokes or trivia, it’s just a good way to engage her and make her remember you so the next time it will be easier to ask her for her phone number.

It takes confidence to ask someone out and women like this in a man. At this point you may not know for sure if she is available and/or truly interested. But you have nothing to lose and everything to gain by taking a chance. The customer in line problem is a drag, in which case you may just have to resort to the business card approach, since it would be too awkward to ask for her phone number while customers are waiting.

We wish you all the best!

Follow-up to above question and answer...

I took your advice regarding the approach. The following is a brief summary of what happened.

I was at the grocery store yesterday and I planned it out so that I could be in her check out line. There was a line of people in front of me and behind me, so I didn't really say much other than hi, how are you? After she was done ringing me up I said, "I hope that I am not out of line, but take a look at this when you have a second." I then handed her my business card, as you suggested. On the back I wrote, "Hi, I shop here regularly and I have been wanting to talk to you, but you are always busy. My name is **** and I would like to get to know you better. My phone number is ***-***-****. I hope you call.

Other than waiting patiently, which is very hard for me to do, can you recommend any other approaches/steps that I should take?

Thanks and thank you for replying to my first question.

First of all, good for you for taking a chance! It takes courage to approach someone you don’t know.

You could simply wait for her to call, but if I were you, I’d keep going in and trying to chat with her. Go in even when you don’t really need to shop and just grab a couple things and if possible, time it so that you have a minute alone with her. Then say something like, “Hi! Remember me? Would you like to meet for a coffee after work if you’re not too busy?” If you have a smile on your face and you’re being genuine (but not too forceful or desperate sounding) there is a good chance she will respond with a ‘yes.’ Confidence and persistence are attractive qualities. (But make sure you’re just persistent and not annoying. Annoying would be going in every day.)

Another thing you could do is send her a flower. Not a whole bouquet because that would be overdoing it. A single rose maybe, but not a red rose because that’s too romantic. A yellow, pink, or white rose would be nice. On the card you can write something like “From your favorite customer” or “To the best cashier at ___ store.” She would be very impressed by such a gesture. Then go in (again try to get her alone if possible) and say, “Did you get my rose?” If there’s time i.e. no customers in line, ask if she’d like to meet you for coffee. Not dinner, not drinks, just coffee. If it’s still too busy then just wink at her and say, “See you around.” And go back and try again in a day or two.

If she doesn’t call you, then it seems like the key to the situation is being alone with her so you can ask her out. In which case you really have to do your homework and be there when it’s not busy. Even if you don’t hear from her, it doesn’t necessarily mean she isn’t interested. Some women prefer not to pursue men. But you’ve let her know your intentions, and if she’s unavailable or uninterested, it’s up to her now to tell you that. If she doesn’t come right out and say, “I have a boyfriend,” or “Sorry, I’m not interested,” then it’s safe to assume she IS interested and available.

Good luck and let me know what happens!

More follow-up to above question and answer...

My name is Cory and I have been bothering you for advice regarding a woman at a grocery store. I wanted to apologize for wasting your time. The reason why I say this is because I am currently writing a paper on sexual harassment for grad school. In this paper I am writing about the different types of sexual harassers. Based upon the fact that I have not really said too much to this woman at the grocery store, I feel that I am no better than some of the individuals listed on the website. Therefore, in order to not make her feel uncomfortable, I will no longer pursue this or even go into that store again.

Let’s be honest here ladies. If a man approaches you the way I did without even talking to you that much, that would rub most people the wrong way. The bottom line here is that I am a coward and will never put myself out there because I only see all of the negative things 10 miles down the road.

The purpose of this comment is to apologize for wasting your time. I don’t want any replies or any sympathy. Again I apologize for wasting your time and the space on your website.

Take care and keep on doing what you are doing because there is somebody out there that will use your advice.

Unsolicited commentary from WWWFM. (We just can't help ourselves!)

Cory did not want further advice; however, I felt it important to comment in this column about his concerns regarding sexual harassment. Sexual harassment is defined as UNWELCOME sexual advances, requests for sexual favors, and other verbal or physical conduct of a sexual nature. Based on Cory’s description of his interactions with the cashier in the grocery store, I didn’t get the sense that she did not welcome his interest, therefore he was not harassing her. If she had said ‘no’ to him or given him clear signals that she wasn’t interested (i.e. frowning, acting businesslike, avoiding eye contact, etc.) then his continued advances could be construed as harassment.

For someone like Cory who feels uncomfortable approaching a woman he doesn’t know, his best bet for meeting women would be to engage in group activities – something he’s interested in where he is more likely to meet like-minded women and – where the group meets regularly and everyone has a chance to get to know one another, at least superficially. Then it wouldn’t seem so out-of-the-blue to approach someone in the group and ask her out.

Everyone has to follow their own comfort level when it comes to meeting new people and if Cory felt this uncomfortable continuing in his quest, then he did the right thing. (But from the cashier’s perspective, she may wonder what happened to the nice man who used to chat her up, and wonder why he never asked her out.) On the other hand, it can be good for us to push our boundaries a little and take a risk. No one likes to be rejected, that’s for sure, but we don’t have to take rejection personally.

There’s a wonderful little book called The Four Agreements by Don Miguel Ruiz, and it’s about the self-limiting beliefs we embrace that negatively influence our lives. One of the “agreements” is:

Don't Take Anything Personally.

According to Ruiz, nothing others do is because of you. What others say and do is a projection of their own reality. When we are immune to the opinions and actions of others, we won't be the victim of needless suffering. I read this book a few years ago and this idea is still sinking in, of how easily upset and defensive we often are because we took something so personally.

A good example of a self-limiting belief is Cory’s statement: “The bottom line here is that I am a coward and will never put myself out there because I only see all of the negative things 10 miles down the road.” The purpose of highlighting this is not to pick on him, just to show one possible negative belief; everyone on the planet has limiting beliefs and many of us aren’t aware of them. The trick is to figure out what they are and ask ourselves questions like,

Where did this belief come from? Did I adopt this from my parents? Is it really true? Is this belief serving me well? Am I willing to let go of this belief?

It can be quite liberating to realize we can just let go of certain beliefs if we want to.

So thanks, Cory, for extending this discussion to a deeper level. Life on planet Earth is certainly an interesting and at times painful and awful endeavor. But learning about ourselves and extending a hand to others is what it’s all about.