How to ask cashier out for date

Question

I am 21 years old and living in a large city in Germany where smalltalk in local markets is not a common thing.

A new cashier joined my local food shop. She’s always at the checkout and never doing stuff like sorting products or cleaning the floor where I could actually ask her out. I am quite new to relationships, but the signs she gave me are promising.

My question is how I can ask for her number, or ask her out for coffee while she is only sitting at the checkout? I mean there are always like 5 people before and after me, and I think it would be awkward if we are changing numbers while customers are waiting behind us. Or even worse if I read the signs wrong and she rejects me? Since the store is just 5 min away from my place I visit regularly and don't want to leave a bad impression there.

Answer 1

There joined a new cashier in my local food product market.

My Question is how can I ask for her number, or ask her out for a coffe while she is only sitting at the cash point?

I would strongly advise you do neither of these things.

But what is your advice? Should I just hope that I will meet her after work at the parking area?

And I'd even more strongly recommend not waiting for her in a parking area!

Try to see this from her point of view. Having worked retail as a female, being asked out is one of the most annoying things that can happen to a person, it can go as far as making her feel unsafe. She's working, and since she's working as a cashier, her job description doesn't involve being picked up by random guys. The only thing that the job requires is that the worker to be nice to their customer (most of the times). As long as she's doing anything related to her job (which does involve commuting to and from her home) you leave her alone. I hope you have the common sense to not stalk her, to find out where she lives or what she does in her free time just to find a loophole and ask her there.

There's a strong bias against guys bothering random girls in shops with requests for dates (speaking from experience). You might get the label 'creep' and you might find that your shopping experience will drop dramatically. She might even get her manager to deny you access to the store. There's a reason advances are looked down upon in these situations: it's not about the no/yes, it's about the fact that the likelihood of an honest answer being expected or given in such a situation is low, close to impossible. You have some power (even implied power) over a cashier with your ability to complain and get them reprimanded, or even because she'll be forced to be nice to you during her shifts even after rejecting you should it come to that.

The best you can do is wait until you at least know her for a whole lot of time longer and write your phone number down, and the next time you finished your business with her you give it to her with a verbal 'I'd like to get to know you, if you want to, send me a message. Here's my number'. Or include a 'Text me/Call me' in the note, and don't say anything at all (this might be more innocuous and have the same effect, since all the flirting up till now has been unspoken, you might want to carry that on). It puts the ball in her court, but at the same time provides some asynchronous communication so that she doesn't have to react if she doesn't want to (which is why I said 'don't ask').

Make sure everything is paid for, and walk away immediately after giving her that card. Also, don't bring it up again, EVER. For me, this was the least offensive way someone ever 'shopped' for me, because due to professionalism I could just ignore it. But if she's more sensitive, even this will upset her, freak her out and make her uncomfortable every time she has to help you again. So, I'd strongly advise against even doing it this way.

Be prepared, your number might end up in the bin with a dramatic gesture, putting you on the spot right then and there, you might be labeled a creep and denied access to the store, depending on how much this tends to upset her. If you get declined, however rudely, don't go complaining. This will make things even more uncomfortable/annoying for the employee and might even cause her to face a reprimand at work if her employer doesn't fully understand what happened.

Your best hope here is to have a random encounter with her in a more social setting like a bar, where it is a lot more socially acceptable to offer someone a drink/phone number if they indicate an interest in you. Don't go forcing this or setting up though, because again that might just gain you the 'creep' label and might seem like you're stalking her however you do handle that encounter.

_{There's a lot of bickering over culture here: I'm from the Netherlands, female, currently 26 years old. I have spent about 8 years working retail and training other boys and girls to work retail ( cashiering). I worked both large city and small town shops. I spent time on holidays (and shopping) in Germany, I am familiar with how retail in Germany, in large cities, works. If the OP says smalltalk isn't a thing, I believe him, and it's another sign that flirting won't go over well.}

Answer 2

I find the other answers very unusual, which illustrates there must be some kind of cultural difference at play.

Where I grew up (the UK) it is completely normal, typical and acceptable to engage in conversation with shopkeepers. Sometimes the entire queue could stop and simply have a collective chat with the shopkeeper about some random thing, such as the weather, and such spontaneous conversations take place frequently. I would even say that depending on the size and style of the shop (i.e. the expected level of anonymity and dehumanization :-) ) it is probably culturally accepted that if the person in front of you is engaging in conversation with the cashier, you politely wait.

Where I live now, in Central European rural areas that latter point is the predominant norm. If you are standing in a queue and the cashier is chatting with the person in front, if you try to interrupt, you are considered to be either in a desperate rush (which would be highly irregular) or pretty rude.

I think OP should probably take advice from local friends and ask what's expected there. This might be a Western European city, or an 'East' German village, who knows.

My advice would be to tentatively engage in a light cashier-related conversation, even if it's just a "Hello again" and a pleasant smile. As the others have pointed out, you have got a bit of a captive audience and that needs to be respected. If she doesn't drive a conversation on her own initiative then stand down and shrug it off. I think the key here would be to respect the fact that she's stuck in that work place and just give her the opening and see if she responds.

In most smaller towns and villages the cashier or shopkeeper gets to know the local community through their role as shopkeeper or cashier. There is nothing in OP's post to suggest for example that he lives in a large city where the cashier is expected to be little more than a machine element. A simple "Would you like to continue this conversation after work some time?" would be totally normal and appropriate. She either says yes or no, and if no you honorably and politely take the rejection.

Answer 3

You could do it this way;

One thing you could do, since you go often to that store, is:

start building a basic "relationship" with the cashier.

Meaning; talking to her each time you go shopping, exchanging some humor and eventually get to know her name. That's not inappropriate at all and could happen in a nice way without putting her in an uncomfortable position. By doing this, you will actually get more insight regarding whether she likes you or she is just being polite.

After you have built a basic connection with her, you can leave a brief note (with a smiley probably) as others have suggested. While giving your note you could say: [while receiving your change] "Thanks...and oh this is for you... You can read it later! Good day!".

Assuming you have written your number in that note, she will text/call you if she is interested, otherwise you should not try to do anything more.

Try to keep your same happy attitude towards her whatever the result. Staying polite and positive even if you get rejected will make her more comfortable rather than being sad or disappointed when interacting with her in the future.

Answer 4

Don't.

Being friendly is literally part of their job description. There's no way to know whether the "signs" you are picking up on are actually signals and not them just doing their job.

Ask yourself how well you actually know them. Have you had a conversation about anything that isn't related to their work? The checkout line isn't the place to have real conversations, let alone get your flirt on.

There's an implicit power imbalance between customer and employee. That complicates the process of turning you down if they don't want to date you.

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If you decide to ignore this advice and try to ask them out, you need to understand that it's highly likely that they aren't into you. Try to give them lots of room to reject your offer without feeling pressured to say yes. After they reject you, accept their rejection graciously. Always be on your best behavior around them in the future.

Whatever you do don't follow them after work into the parking lot. That's borderline stalking. You don't want to be banned for harassing employees who didn't want to date you.

Answer 5

Your interaction with the cashier is constrained by work rules (she has to be nice to you) and also social norms. The degrees of freedom available to signify attraction are few. Also, ten creeps have delivered sleazy pickup lines to her since this morning, you don't need to be the next one. It's her job to be nice to you, don't mistake this for her giving hints that she's interested in you.

In a bar, she could just turn around and leave, but not here. The cashier's problem is that she's stuck behind her cash register. So if you arrive and dump your emotional train wreck on her, like drop to your knees, pull out the guitar and go full-on Romeo on her, she'll have to stay put and silently cringe -- "G'aaah not again!" -- until you get the message, and she's not gonna like it (see Tinkeringbell's answer for examples).

Therefore, don't ask her when her shift ends, or to meet in the rapey spot at the back of the parking lot, after her shift, when it's all dark and gloomy.

If you really, and I mean really think she's interested (and I mean really, like not in your dreams) slip her a phone number and that's it. Give her an easy way out. Don't make it awkward. And don't stand there making big puppy dog eyes and blubbering while you wait for her answer, just "see ya" and leave. Don't look like you're gonna make a scene and attract the attention of her boss!

There would seem to be a paradox, in that lowering the cost of rejection for her increases your chances of success, but there really isn't a paradox. Communicating that it's no big deal if she says no shows confidence, and also shows that you haven't been writing romantic poetry thinking about her for the last six months while you have no idea who she is (creepy-creepy) rather you're just interested in getting to know her and have a drink. You catch feelings after you get to know her, not before.

And above all, don't pressure her. You can't pressure a woman into being attracted to you. That's what "creepy" means. Attraction is not the result of a negotiation. Either she's attracted to you, and you create the circumstances where things will happen, or she is not attracted, and you move on.

If you're awkward around women, and the cashier is the only girl talking to you in your whooooole entire life, then try shopping in another supermarket. The cashier will also talk to you. The girl in the booth at the post office will also talk to you. It is a safe bet that they're all just doing their job. Don't think a girl is attracted to you because she's doing her job. Try a man cashier. He will also talk to you.

This shouldn't stop you from being nice to the cashier, or the post/tax office girl. In fact, the last time I was nice to the tax office woman, I asked her if I was the first dude not to yell at her today. She said yes, and since it was 5PM we shared a glance of understanding for a few seconds. That's just basic humanity. What I say may sound weird to some, but you can actually be cool and nice to women without any second thoughts.

Anyway. Back to this cashier girl. In my case, it was simple. We never talked beside "hello". I put the money in her hand, and then she gave change back. We looked into each others' eyes for about two weeks. It was pure stare porn, and she flushed and sighed. That's a pretty good indication something's happening.

One day, I put the money in her hand, and tickled her palm. She flushed, returned the change, and caressed my hand in return. Then she returned change in copper coins, one at a time, staring me in the eye. The amount was wrong. I got the message.

Next day I slipped my phone number on a piece of paper, didn't say a word and left. She called, and shortly after she was on my couch.

The next day, as I entered the shop, the whole personnel (all women) grinned at me. Some talking must have occured behind the scenes...

Much later, she told me she was married. To the owner of the shop. This is why her name is "girl" int this post.

EDIT: another one, I had forgotten!

So I go into a shop to buy some shoes, it's a bit of an oldskool shop where you ask the saleswoman to fetch a box of shoes, try them, etc. She seemed interested, so I just asked "Are you new here? I've never seen you before." Or something like that, I don't remember, it doesn't matter anyway. Note I had never been to that shop before. Then we had an interesting conversation about her other job (comic artist), and I left with her phone number. We met a few more times for drinks and visiting expos but no further attraction developed, so nothing else happened.

Answer 6

I suspect answers can be highly different depending on the cultural context. For instance - southern Europe here - to me it's perfectly acceptable to engage in small talk with the cashier. I expect it to be more difficult in a big supermarket than in a small shop, but I wouldn't label this behaviour as non respectful.

You can try going to the supermarket at different times, e.g. very early in the morning, to find a moment in which the supermarket is emptier than the norm. You can engage in small talk then, without a long queue forming behind you. Start with neutral topics (the weather is an evergreen) and see what her response is. Do this some times. You can deduce from both verbal and nonverbal cues what her feelings towards you are, whether she's friendly because of her professionalism or because she actually wants to be your friend. For instance whether she looks at you in the eyes while answering, if her answers are short, if she asks you something as well, etc.

Most importantly, if you see that she doesn't want to engage in a conversation with you, do not insist. This is impolite and quite creepy. Remember that she has to be somewhat friendly with you, don't force her to behave friendly against her will with someone she sees as a creep.

I'd advise against going straight to her with your phone number on a piece of paper without having some small talk before. To me, it'd come across as a creepy behaviour. I'm aware that Germans are renowned for being very direct people, though, so it could be the right move to do after all.

Answer 7

Asking her out directly seems like a bad idea.

Instead, in these situations, I've found something that works much better for both of you. During your conversation with her, mention some place you're planning to be in the future so she can find you there if she chooses.

For example: "I like to grab lunch here before going to [Public Event You Enjoy]"

This could be almost anything, but here are some examples:

• A place your band plays
• A public dance
• A painting/pottery class
• A wine tasting

This should be something you actually enjoy, so be sure to let your excitement about your hobby be apparent when you mention it. Ex: "I enjoy that they let you try lots of different wines from all around the world!"

If she expresses interest in the activity as well, tell her more about it so she can attend: "Yeah, it's really fun. They do it every Tuesday and Thursday at 7pm - the admission fee is 5 Euro. You should check it out sometime!"

If she is interested in you and has time, she will probably arrange to come to the event some time and you will see her there. This is preferable because she is not under obligation to behave professionally for her work and you can spend some time chatting as equals.

And if that goes well, then you have created a good opportunity to ask her on a real date. And if she doesn't come, well, you were planning to go there anyways so it's not a real loss on your part - you just spent an afternoon/evening doing something you already enjoy.

Answer 8

I understand the situation, and if you really want to know her and you think the signs look good, then I suggest go for it.

I suggest you consider the following: Is she especially nice to you, or is that her normal behavior with many customers?

You could also do a step in between. If you buy e.g. some cookies, ask her if she knows if these cookies taste good. Or if she can recommend some better-tasting cookies. Or if you buy a bottle of wine, you can ask her about it. I guess you will soon find out if she answers e.g. "I don't know and I don't care" or if she answers something like: "I love those cookies, I wish someone would invite me to eat them."

If you do this one or two times, you should get an idea of how she reacts. If she does not react then forget it. Asking her 10 times more won't bring a better result.

Take it easy, look how she reacts and accept it even if she is not interested in you.

Answer 9

I generally agree that it is usually best not to ask people out at work. However, it has happened from time-to-time. Having been on the receiving end, I can tell you I've always found it awkward and uncomfortable when someone has asked me out as opposed to leaving a note for me to choose to respond or not respond privately.

Another option you may consider is going through her manager. As an anecdote, we recently had an emergency drill that involved several different departments at my place of employment. One of the firemen involved found one of my coworkers to be attractive. He maintained professionalism through the drill, however, and never so much as asked her name during the drill. When the drill was over and he returned to his station, he asked his supervisor for help in reaching out to my coworker. The supervisor reached out to the safety manager; the safety manager reached out to my department manager; after the safety manager and department manager worked out who the fireman was interested in, my department manager approached my coworker and explained that one of the firemen was interested in asking her out. Most notably, the fireman passed his number through those people to give to her, and left it up to her to contact him if she was interested.

The key aspects of this are that

• business was business; and business with her was not interrupted for personal reasons.
• the supervisors were involved to pass the information from him to her. More specifically, he did not go tracking down any of her information.
• her safety and comfort was maintained by having someone she knew and was familiar with approach her discretely
• everyone involved was confident that if she had declined, that would be the end of it. In your case, if she declines, you must never mention it again and pretend like it never happened.

Answer 10

As several others already have replied - it depends where you are and the (as yet) unknown chemistry between you and the cashier. I live in Denmark just north of Germany so it's not completely unfeasible that there are some similarities.

About 15 years ago I met a girl working at a local convenience store. We started small-talking (weather etc.) and after a few encounters we started really talking if there was no other customers around. At some point we realized that we needed to meet outside the store to really talk, which we then did. We met for coffee, later for a meal, and while we never became a couple, we did end up being best friends and we still are to this day. We talk every day and meet a few times a week. We go on vacation together, we spend holidays and new years together and so on. So everything is possible but it has a lot to do with the interpersonal chemistry. While I've known this girl she has blocked or otherwise shut out countless guys trying the same thing and that could easily have been me as well. But unless you try you'll never know...

So try some small-talk and see where it takes you, but be polite and do not ask for a date up front. That will most certainly backfire. If she's completely unresponsive stop immediately. She's not interested.

Answer 11

My suggestion is to not overthink this or make it overly complicated. Just be polite. If you ask her as you are going through the checkout say "hi, how are you doing?" Hopefully she will respond. If she does just ask her if she'd ever consider having coffee with you. Make sure you speak clearly. Be very casual about it. She could say yes, no, or not respond to the question.

A "yes" response would be very cool and and allow you to follow it up with a proposition like, "sometime this week at x coffee shop, is there a good time?". Something short and simple and easy for both of you. Maybe you don't need her number and she can just show up at a place and time. If she says "no", just say "no problem, thanks". If she doesn't respond, just say "thank you" as the transaction completes and you depart.

If she did say "no" or not respond, after that interaction as you continue to go to the market, just behave casually as you normally would and if you go through her line be polite and friendly but with no expectations. It would probably be best to not think about it any longer. She could always change her answer or answer in a positive way to give you more information. But at least you put the ball in her court but have not placed any demands. And if she did come back at a later time and ask you for coffee, it would be a very great surprise.

Good luck!

Answer 12

First, a little frame shifting

You want to court her. Assenting to courtship is an act of whimsy. What are the prerequisites of whimsy?

I must disclose agenda: I want a world where women are inherently safe and empowered. Hardly altruism; that works in mens' favor too. Point is, right now they don't, and men "doing our usual" isn't going to move the needle.

Back to the prerequisites of whimsy. As it happens, safe is the first one. Can't be whimsical if you're worried about life or food or shelter or someone who seems a threat. You can guess empowered is too, but there's a third: ability. If she can't fit dating into her schedule or budget, if family or social or work issues prevent her (can she date customers?) then nope.

Special issue: when one is working, one has to do ones job or get fired. Worse the job requirements often entail being nice to customers, and definitely engaging customers and remaining at ones post. That fact can confuse the romantic, so special handling is required.

This is also a longshot. Probably about a 95% chance she either is already partnered or not looking, for some good reasons you can't override. On top of all the other overlapping chances of something else being in the way.

It's also good to sanity-check your own motivations. Make sure you aren't unconsciously seeking self-validation of some kind. If "no" seems like it would damage, hurt or invalidate you, get to healthcare and work that out. That is a requirement of the principle of safe -- which also applies to you. And there's the factor that when men are hurt, they sometimes hurt back. Her having to worry about that violates the principle of empowered.

Since it's about whimsy, the goal here isn't "yes" - the goal here is "why not?"

So we can cross off several wrong approaches

Giving away ones phone number is a safety risk for the girl with indeterminate reward - silly to ask. A phone number may be voluntarily given later, but should be asked for by saying "hey, I'd like to stay in touch with you" and let her choose out of the variety of contact methods that exist today.

Asking while she is serving you as an employee violates empowered because she is effectively cornered: she can't step away, she has to serve you. There's no freedom of motion for her.

Too direct an approach also creates a Huge Awkwardness when you visit the shop in the future, as now she must explain her rejection. Awkwardness is the enemy of whimsy. That may not have occurred to you, but like I say, "men doing our usual" doesn't create any safety or empowerment. Any approach must provide an easy exit for her so there'll be no uncomfortable conversations next time.

Again, not altruism: it's in our interest; the path to "why not?" isn't found by making her uncomfortable.

The open door

Since your hunch is that she does like you, all you really need to do is open a door. This doesn't require breaking any of these rules, but it requires finesse. Consider a series of improving options.

Hi. My band's playing at the Speakeasy this Thursday, and I wanted to let you know about it. (gives performance flyer)

By the way, having this sort of opening is a big reason boys start rock bands. Anyway, it doesn't have to be a rock band, it could be a sporting match, play, whatever - just as long as it's a small enough venue (Taylor Swift concert is much too large) and the entry cost isn't too high. It has to be something any random girl would find enjoyable all by itself even if you weren't involved.

But we're still not clear of the problem of putting her on the spot. She may feel like she has to accept or decline right there. She will expect you, on next visit, to quiz her about "did you come?" or "Did you enjoy it" or even worse, "Where were you?"

I mean, aside from the 95% factor, she may have a prior engagement that night, so her failure to appear is not even a rejection, and she doesn't want to worry about you feeling like it was.

Oh sorry, I'm a little distracted, I'm trying to get in the zone. My band is playing at the Speakeasy Thursday night and it'll be our first performance all year.

Much better, now we've avoided putting her on the spot, we've just slipped her a little bit of intelligence, with no request whatsoever for her to act. She might followup with other questions like "what time?" and in that case, don't answer in a way that creates the expectation. She will appreciate you phrasing it in a way that doesn't put her on the spot.

The flaw in this approach is there isn't really an explainable reason for telling her that. I don't think it'll make her uncomfortable, but there's a finer way still.

Who do I talk to about putting something on the store's bulletin board? My band is playing at the Speakeasy Thursday night, we're so excited."

Fair chance you'll get a "Oh, I'll put it up for you" or "We don't have one, but I'll put it in the staff break room". Here, you're just leaving a breadcrumb trail. If she's interested, she'll follow it unless unable. And it's low-impact enough you can do something like it several times without any appearance of being creepy.

Answer 13

Since you're not asking if you should or not but HOW you should ask her then I'd suggest you to try to ask her something like "Hi, I was wondering if you'd like to have a coffee/drink with me sometimes ?".

If you're feeling insecure because of the people around think about how it can make her feel too, either she agrees or not it will also put some pressure on her so try to do it when there's no one around, and be prepared to leave either she agrees or not. If she does, give her your number and leave, if she doesn't just leave and act like nothing happened, you don' want her to look at you like a creep or something.

This is an advice about how to do it, now keep it mind that people mostly tell you not to do it. It's up to you to weigh the pros and cons and do your choice, make the one which will leave you with less regrets as possible.

Answer 14

Plenty of wise advice already. Some points of potential special cases.

At my local supermarket, some of the cashiers take smoke breaks near the public the entrance of the supermarket. If you naturally pass by there, it may be OK to stop for chit-chat. It's long enough to exchange more than a couple of sentences and gauge interest. She has an easy escape: "Back to work, bye". It's public enough (assuming there's people around) and therefore reasonably safe, but private enough to not be embarassing. Of course, if their smoke break is in a back alley behind the supermarket this can't work (seeking her out there would constitute stalking). And don't stand somewhere waiting for her to take her smoke break, only do this if you naturally happen to pass by her having one.

Or you could be lucky and run into her on a bus or somewhere else out of context. I once stayed at a youth hostel, the day after I checked out I ran into one of their employees on a bus, 200 km from the hostel. In a different life I might have chatted with her more than I did. Again, only partake this if it genuinely is by chance.

Answer 15

Variant of the answer by @Harper.

Mention some public event coming up in the upcoming week that you are planning to attend, such as a concert, puppet show, debate, whatever. Example:

Did you hear, So-and-so is going to be performing at the (venue) on Thursday? Should be a great (event, e.g. concert).

If she perks up and looks interested, you can respond with something like

Well, maybe I'll see you there! I'll be wearing (something noticeable, such as a red hat, which hopefully you are sporting the day you visit the store).

Even if she's busy on Thursday, or does not share your interest in this type of event... it's a first step.

Answer 16

If you do say anything, I suggest giving her an easy out, such as: "Would you like to get coffee after work, or do you have a policy against socializing with customers?"

Note that I am not recommending you ask her out, just suggesting a way of making it easier for her to say no without either of you losing face. Of course, if she tells you she has a policy against dating customers and you later see her dating another one, don't call her on it.

Answer 17

Don't jump to asking for her number, build rapport first. Get to know her (over a few visits to the grocery store) and in the process find somethings she's into. For example maybe she likes art and you can suggest to her going to an art gallery together. If she seems to like the idea, then exchange numbers. Since there's a lineup it may be easiest if you have your number written on a piece of paper to leave it with her.

Also regarding not having much time because there's a lineup. Try going into the store when it's not as busy. Or buy more items so you have more time to make small talk.

Answer 18

I have read most of the answers, but none has found themselves in your situation.

I did.

There's this cute girl at a local shop that I visit every day. She's very vibrant and given we're a bunch of meat, you ought to give in to your instincts.

Or do you?

Well, let's think about this:

I believe we're all mature enough to understand the fact that people react differently to you based on how they feel about you. This, in turn, is affected by how you look, how you smell, what you say, but for basic sexual pleasure - looks are everything.

For a male, the odds are stacked against you. A woman, by her nature, is careful with whom she picks as her mate, biologically speaking, women carry a big responsibility for their off-spring. They can't just go around giving in to anyone, they have to be picky. Even these women who we'd call "easy going" only go for what they feel is biologically safe / sound.

With this knowledge in mind, she's common-senseley (making up words!) not into you, unless you look very good.

And if you did look very good, you wouldn't ask this question, so I'll make the assumption.

In this case, it's simple: you get rejected.

And this is where our similarities come in to play:

I was thinking, had I not had a girlfriend, would I ask this girl out? Assuming she had no boyfriend and was available, what would she say?

Probably a big no.

But what happens after, due to the dynamics of her life is, every time I go to that damn shop, she will feel somewhat at unease. She'll now believe I go there just to see her and while you can't be judged in court for this, she will think it's creepy, she'll then tell her co-workers and they'll start to subtly take a pick on you.

So, I'd say - don't.

I know you will, though, I believe questions related to love on this site are mostly looking for that one answer of "do what your heart tells you", but seriously - your best bet, really is to establish rapport in another way.

I'll just assume you're somewhat smart as to not be caught doing this and that you've already made your mind up. My goal here is to help you not mess up.

Build a relationship first, as one answer notes. Try to engage her when you see her, but just minimally. Don't offer compliments, rather, try to just be friendly. Once you feel (please, do try to assess objectively) she's feeling somewhat comfortable, go in for a more direct hit.

You were thinking about tackling her during work? Wrong. This will not get you a natural reaction and is prone to outside interaction from her co-workers and such.

Try to see when she gets out. Casually go her way, drop something or try to create a natural interaction, then start conversation.

Here's where you'll go wrong, due to these butterflies, oh man -

You won't know where to stop and it'll turn creepy.

I'd say just letting her know you exist, more than simply being a stranger is enough for now.

The ball is in her field as of now and she'll be the one to decide if she wants to play.

I hope this helps. Being a little bit creepy, is okay, if you can't help it (you should), but don't be a stalker. No one likes that.

Good luck.