So the other day I was at Staples getting supplies for some used bookselling I do on the side, and as I was paying for my stuff I noticed the cashier. Being Staples I imagined it was going to be some frumpy, overweight, unattractive, etc person, but I was pleasantly surprised that she was actually kinda hot, in a nerdy shy introvert way. Behind the frumpy hair and the mandatory baggy clothing, I would say she could definitely be a 7, especially if she had the body language (which she didn't seem to). I kinda have a soft spot for the nerdy shy introvert type of girls - the ones who are hot but just totally don't know it.

Like my wallflower pathetic self, I only noticed how cute she was about half way through the checkout, at which point I froze up and just stared at her, not know what the heck to say. Preferring to daydream about her on the drive home rather than actually having struck conversation with her.

Today I have to go back to Staples to get more supplies and I wanted to strike conversation with her, but really do not have a clue how to talk to her. I'm inexperienced at this kind of thing, and not sure what sort of banter would be useful without looking like I was blatantly hitting on her. Also with her being a cashier, time talking is short.

The only openers I can think of involve either asking how long she's worked there (acting like I don't recognize her from my previous shopping experiences), then go from there to ask about stuff like school, interests, liking work, and if she's got any computer geek in her or whatever (I am a web developer, so I could mention that).... Or I could bring up why I'm buying my supplies (to print out an e-book on "self-help", heh heh) - though I don't see how that conversation is particularly open ended or where I can ask her questions she would answer.

It would be some miracle if I could actually strike enough rapport/common interests that I'd get some contact information (ie maybe a facebook account). Though I'm not sure how to go from canvassing for common interests to suggesting further contact outside of the store, in a way that makes her feel like it's a great idea. Keep in mind that she's a cashier (probably will be someone behind me in line, though I can wait to get in line until there's no one else around), and that being the shy introvert (looking) type, canned openers need to be more subtle and substantial to not freak her out.

Perhaps I should just get the conversation as far as I can and then make a habit of regular (ie once a week) visits to the store to get more "supplies"... and continue the conversation from there, with some sort of rapport already established. It may be wisest just to aim for finding common interest the first time around?

I would imagine that my first goal/milestone is to get her to think that I'm an interesting/cool person, through discovering common ground and then explaining my relevant interests, skills, etc. So she can at least like seeing me again to continue talking at another time.

I would think that if I were to somehow get her contact information, the most likely circumstances would be if it were for the purpose of providing some value, such as if we found common interests and I knew of a resource or something that I could share with her (me showing off my knowledgeability). Though I don't know if that's "closing" way too soon and there needs to be sufficient rapport/comfort first, before she would feel comfortable sharing her contact info? I would imagine there are subtle signs (I'm not yet attuned to gauging) to show how open she would be to connecting out of the store.

Aah dude, I see where you are coming from and heres a few pointers which hopefully should get you far with her. As a PUA you should always remember Peacocking - a feature which will make you stand out amongst her everyday people who she serves. This is merely to grab her attention which may lead her to ask about you or why you are wearing that silly hat or glasses. Chances are, being shy as you have described her, she wont say a thing. So here are conversation starters

1. Just say "you look terrible (this is a Neg), have you been working long or are you being overworked?".. regardless of her answer yes or no.. just say you look like you could use a break! hopefully she should say.. I could use a break indeed or I go on a break in 30mins or whatever.. you can close with either asking what time she goes on a break if she doesnt volunteer this information, or if she does then asking do you mind If I join you on your break.. I could use a break and some nice conversation for once and not the nagging of my boss.

2. Use what you can see on her to start a conversation. It only has to be small short conversation to make her think.. or I want the conversation to continue. So for example, If she has a badge with her name on it just ask "your name wouldnt happen to be [insert her name] would it".. Hopefully she'll say.. you noticed the badge.. which will enable you to say something along the lines of "do you always volunteer your name to strangers?" in a jokingly/teasing tone. You'll make her smile. Follow it up with "I volunteer my name to strangers all the time too, Hi [insert her name] my name is [insert your name]. This should ease the "I am serving only tension" mode most people at the till put across. Just before you leave or whilst packing the stuff she is barcoding through to you just start telling her something i.e. did you hear about the shop keeper in Ohio who had his name stolen because he used to have it on his badge?.. then just turn around and say oh thanks I'll tell you it another time. Hopefully you can come up with a more plausible story which will intrigue her. Then walk away without finishing it. go back another time and say I'd like to finish that story over lunch or if she asks you to finish it (demonstrating value), say its quite long, are you free for lunch?..

Good luck buddy!

Observations are the key. improvisation is the lock. Add wit and charm for a smooth finish