Asking a girl out IRL…

I had a reader send me an e-mail recently about a situation he has found himself in. There is a girl that works at a local establishment that he visits. He is attracted to this girl, and thinks that it may be mutual, and would like to know if he should ask her out.

The answer is…YES!

Any opportunity where you don’t ask a girl out is an automatic failure. That is why I have never hesitated in my life to give my phone number to a complete stranger. The worst thing that can happen is NOTHING. You never hear from them again! Then at least you can rest easy knowing that you tried, and you never have to sit up at night wondering ‘what if’.

There are some major things to consider when you are contemplating asking a girl out in her place of work. This procedure needs to be accomplished with more grace and caution than an online girl, or some girl at a bar. Depending on the nature of her job, she could be surrounded by coworkers and other customers at the time you make this attempt. This is why you have to make sure to do it in the right way.


Chances are this person may not always be the one taking care of you when you visit the establishment. For example: If this girl is a waitress, you might not be seated in her area every time you come in to dine. DON’T request to be put in her area, or offer up your spot in line in order to have her waiting on you. Co-workers TALK, and this seemingly safe maneuver can result in her thinking you are being creepy. That being said, just because she isn’t the one that takes care of you, doesn’t mean you can’t ask her out. Don’t try to set up the Hollywood romance scene that you have been day dreaming about. She isn’t going to throw her notebook to the ground and undo her hair and take you on a table…IF THIS HAS EVER HAPPENED TO ANYONE — PLEASE TELL ME ABOUT IT! I WOULD LOVE TO HEAR IT.


It may be tempting to begin the conversation with a simple compliment to engage her… I actually had a pretty intense debate with a male and female friend of mine the other night. The male believed the compliment was necessary in order to set the tone. However, the two of us girls agreed we would much rather NOT be complimented at this time. There are a few reasons why the compliment is NOT a good idea…

  1. The compliment can draw attention to the situation. As I mentioned, there is a good chance coworkers and other customers will be in ear shot of this conversation. I might not care to eavesdrop on another transactional conversation between my coworker and a customer, but the second I hear something a little less transactional…my ears perk up. You DON’T want to DRAW ATTENTION to this conversation! It can embarrass her and do the exact opposite of what you intended with the compliment.
  2. The compliment defines the intentions. Girls are very analytical when it comes to the opposite sex. We will spend hours tearing apart a single sentence to find some underlying meaning to it. If you compliment her, she will likely assume you are wanting to date her, or have sex with her. This puts the pressure on, and can make her shy away from texting or calling you.
  3. We are girls…we get compliments ALL the time. Your lack of compliment can actually separate you from the pack and make you seem mysterious and more intriguing to the girl.
  4. We don’t need a compliment to make us smile, your phone number is PLENTY.

Once you have successfully given her your number and received your first text from her, that is when you can open up a little bit more. I am not saying to never compliment the girl, but I think at least in the initial swap it should be avoided.


It is extremely important to keep this interaction very short and to the point. This benefits you in a few ways…

  1. You leave her wondering. If you don’t say a lot and just offer up your phone number and leave, she is going to spend the rest of her shift thinking about you. She will probably spend the better part of an hour staring at the slip of paper you wrote your number on…just wondering…
  2. The short interaction leaves less time for anyone to notice it is happening. This means she won’t feel embarrassed or be hounded by her coworkers who will offer to help her tear apart the situation. She can instead feel good about herself and go on with her normal workday.
  3. You won’t be seen as an inconvenience to her when she is trying to perform her job. For example: If she is a Barista, she likely has a zillion things to do and can’t spend a lot of time talking to you. She will APPRECIATE your thoughtfulness in being quick and to the point.


Do not ASK her a question. Do not say “Would you like to go out sometime?” or “Can I give you my phone number?” This opens up the opportunity for her to make a quick assessment and say NO. You stand a much better chance with this girl if you put the ball in her court with time still on the clock. Simply say something along the lines of…”Hey I would be interested in getting to know more about you, here’s my phone number, text me if you are interested.” It is THAT SIMPLE. Then WALK away. When you walk away, don’t just storm out like a coward. Walk casually off to the exit, and make sure to turn back and look at her. Don’t look at her like a CREEP, but just a soft gentle glance, and then keep on walking.

The reason I suggest the look back, is because it shows CONFIDENCE. You are not afraid to give this girl your number, and you’re NOT afraid to look her in the eye. Do not ruin a perfect setup by putting your tail between your legs and stumbling off like Napoleon Dynamite in a head first run. The look back also gives you the opportunity to see her true reaction…is she smiling? Is she tossing your number in the trash? Is she gushing about you to a coworker? You might catch a peek of that as you turn to look which can help you determine your chance of success.


After this interaction occurs, unfortunately you might not hear from her or you might get a text that says she isn’t interested in hanging out. The important thing is to just ACCEPT the fact that she isn’t interested. Do NOT bring it up to her again. This is a risky deal because chances are you frequent this establishment. It could be a restaurant, bank, grocery store, and anywhere really. You don’t want to make it awkward for her or yourself when you have to visit again.

The most important lesson that I hope you take away from this is DON’T be afraid to take a chance. You might not get the response you want, but it is a hell of a lot better than never knowing. The majority of the relationships that I have been in started from someone taking a chance. The worst thing that can happen is they say NO, but you’ll never know until you try.

Have you ever taken a chance and asked out a person at their place of work? How did it go? Ladies! Weigh in! How do you feel about being complimented at your place of work by a customer?  Please comment below with your thoughts and opinions! I look forward to reading them!

Thank you so much for taking the time to read! I hope you all had a safe and happy Halloween! We did a Rock & Roll themed Halloween at my work:

Rock&Roll Jenn

Rock&Roll Jenn

What did you dress up as for Halloween? Please follow my blog if you enjoyed what you read and would like to read more! You can also follow me on Twitter @how2cupid for updates! If you have any comments or questions that you would like to share privately, you can e-mail me @ Thanks for reading and happy soul searching! xoxo


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