Whether to Initiate Contact With Barista [duplicate]

Question

I frequent a particular coffee shop 3-4 times a week, and am pretty familiar with the baristas, as I see them often. I've noticed one of them, C, is flirty and playful with me, and seems genuinely happy to see me when I come in. I'm interested in getting to know her better, but so far our interactions have been limited to brief conversations over the register. I've tried to occasionally steer conversation away from work, but she's busy and on the clock, and I don't want to be the asshole holding up the line. Knowing that what little relationship we have so far is business/customer related,

1) Is asking her out at work likely to be unwelcome/irritating/too aggressive?

2) If it is, are there alternative ways to initiate contact that are less abrasive? E.g., would seeking her out on social media be appropriate, or just weird and creepy?

For social context, I am in a small town (<20,000) in the United States.

Answer 1

The answer is:

You don't.

Don't ask out your barista; she is there to work and is required to be nice to you. You'd make her really uncomfortable by asking her out. If you see her outside of work, you may perhaps try and ask her to hang out -- but never do so, when she is at work.

Don't wait for her to get off work either -- that's creepy and would scare her.

Don't follow her around your town either -- that's also creepy and would scare her.

The best thing to do is to just leave her alone, but on the random occasion that you two run into each other, outside of her work environment, you'd have your opportunity to ask her out.

Having said that, I'll share a personal story (for reference, I live in New York City): I recently became Facebook friends with a really cute girl that I liked - she worked at a nearby ice cream shop. After a couple of years of friendly, caring, professional relationship with her, I finally decided to give her my full name and number, written down on a piece of paper. She had outgrew her position and was leaving for a new job (still in New York), and I asked for her to keep in touch. She added me on Facebook the next day, and we've been having really nice conversation on Facebook messenger ever since :)

Answer 2

It depends

My advice is based on experience made in Russia, not US, so keep that in mind.

It is true that baristas and cashiers can be paid for being nice, or for having customers return to them. In this situation, if you ask her out, you can make her really uncomfortable, especially if you hold a long line for that purpose.

Trying to find a time when she isn't busy with her work (like when the customer flow is small) isn't a good idea: if she is just being nice because she gets paid for that, you will make her even more uncomfortable because she won't have an excuse to stop the conversation.

On the other hand, you can try to watch how she interacts with other customers (find a table near the cashier's desk). If she "flirts" with all of them, she is not flirting, she is just nice to them. If you think that her behavior was special with you, probably go ahead and try. Although you can still be wrong, so stay careful.

Don't stalk her, e.g. don't try to add her in Facebook, chase her in the city, "occasionally" meet her in a shop, in a swimming pool, and near a bus stop, etc.

You can politely pass your contacts on a piece of paper, as @D.Hutchinson suggests. It can be your phone number, or your Facebook address -- anything. But be prepared for a silent rejection. Or any kind of rejection. Yes, if she doesn't respond, it means a silent rejection and you should drop any attempts to go further. No, it doesn't mean that she has lost the piece of paper, if someone loses your contacts but wants to stay in touch, they try to get the contacts again the next time they see you. So if she doesn't ask you for your contacts the next time she sees you when she is not as busy as usual, stay back.

If she contacts you -- go ahead, that's your chance. :)