I am a shy guy; I am planning on asking this woman out.

I have seen and even spoken to this woman less than a handful of times over the last year or so. This stems from the fact I only ever see her at her work; She works in a fast food restaurant. I stop by this fast food restaurant 3-4 times a month on my way to work sometimes a little less often. She has only been working in the drive-thru window one or two times. Because she does not work the window I am having a hard time figuring out how I can ask her out for drinks without feeling like I am yelling to the whole restaurant and I would also like to make sure I make it the minimal amount of potentially uncomfortable for the both of us.

I dont get whats the purpose of posting this here sir ,with all due respect.

I mean if youre taking permission then sure, go at it,or at least let her know youre there, wish you all the best of luck!

Well, I could be wrong, (and Edward, please correct me if I am), but I think he's looking for advice on HOW to ask her out. In other words, he's saying he doesn't want to do it through the drive through because that is kind of awkward and also basically broadcasting him asking her out to all of her surrounding co-workers.

I definitely understand that. You said she only sometimes works the drive through, correct? So, I'd say maybe find an excuse to go INSIDE some time rather than using the drive through. Find a time when you can find her with as much privacy as possible. It's a public place, so it is doubtful you'll ever be completely alone with her, but at least find a time when she's off by herself. Maybe sitting at a table taking her break, or cleaning tables or something.

Strike up a brief conversation with her then and use that as an excuse to ask her out. I agree with you that the drive through isn't really the ideal place. It would be great if you could interact with her outside of her work, but since you don't really see her anywhere else, finding her on a break or otherwise off by herself may be the best time.

Being another shy fella, I know how you feel and know you will probably WAY overthink what you are going to say. So, I'll say this.... There are two approaches you could take, so go with what you think would work best for you.

A) Do your overthinking BEFORE you ask her out and get it out of your system. Come up with the basic idea of what you are going to say so that you are prepared and don't just stutter and stammer, but at the same time, don't OVER-plan it. Let it flow naturally.

Or

B) Ask her out before you can overthink it. It may be possible if you overthink it, you'll just never do it because nothing will ever seem like the right time, and you'll psyche yourself out thinking too much about all the possible negative outcomes. So, don't overthink it and just go for it.

Most people will suggest option B, and it honestly is usually the best advice. The thing is, I personally know from experience that it just doesn't work for everybody. I'm extremely shy myself, so for me option B does not work. I'm too shy to the point where if I just try to wing it completely and just go for it, I don't really know how to do it/what to say, and I just wind up sounding like a stuttering, stammering idiot.

I NEED to plan these sort of things somewhat. For me, the trick is just having the basic idea of what I want to say so that I have a sort of game plan ahead of time.... but also remaining flexible to the situation. I know from experience that, for guys like us, sometimes just winging it really DOESN'T work. However, overthinking it will also not work. So, whether you think option A or option B is more your speed, give it a try and just go for it.

Good luck!