So you’ve spotted the possible girl of your dreams at the local coffee shop—and she works there. Your immediate instinct is to hit on her. But she’s a barista—she gets hit on constantly, and her first instinct it to shoot you down. And then what do you do? You blew your chance—and worse, you still see her every day when you get your caffeine fix. So stifle your instinct and remember our basic rule—repeated exposure. After all, you’re going to see her every day; you don’t need to rush. She works there.
At least, you’ll see her every day if you know her work schedule. After all, maybe she’s just filling in for another counter girl when you first spot her. If you don’t see her the next time you get coffee, simply ask another barista—“Hey, where’s the cute blonde that was working yesterday?” The response will be along the lines “Oh, Cindy’s off today” or “Her shift doesn’t start for another hour” or “she’ll be back tomorrow.” (We baristas tend to be helpful like that!)
So now you know when “Cindy” is guaranteed to be there, a sitting duck for your suave moves. Resist making those moves. Repeated exposure, remember? Start with “hi” and idle chit-chat before moving on. Unlike pursuing a fellow customer, you don’t have multiple locations with their varying encounter opportunities. So you have to take your opportunities when you are at/near the counter. But chat during the business transaction, not when she’s actually making your drink. A distraction at that point and she could screw up your order, or worse, burn herself. Not the type of memorable interaction you want. When possible, sit at the counter. It lets you chat between customers, while she’s doing those little things that are part of the job—wiping the counter and tables, restocking counter supplies, prepping fresh pots of coffee, and so on.
However, counter girls don’t actually spend all their time at the counter. Sometimes they’re taking out the trash. Once you’ve established your regular presence as a good guy, you can offer to help carry it. Save her the drudgery and show you’re not afraid of unpleasant labor. And sometimes they’re taking a break. This, however, is not a good time to approach her. It’s her job to be friendly and she probably needs not to be for awhile. As the rule of repeated exposure comes into play, however, she might decide she’d like the company; so make yourself available, but not intrusive.
When dealing with counter girls as opposed to fellow customers, there’s one factor to keep in mind—she needs rescuing. Probably. One of the (now ex) boyfriends I got while I was a barista once told me he knew he had a shot with me because I needed to be rescued. He was right. And so does your girl. Let’s face it—counter girls (even when they’re called baristas) still make minimum wage. They need rescuing from poverty and the problems that go with it. The one thing you don’t do is offer her money—it’s crass and disrespectful, especially when you’re trying to get a date with her.
But you can provide other kinds of help. Is she going to school? Maybe you can offer advice from your own experience. Are you knowledgeable about one of her subjects? Maybe you can offer help in studying.
If she doesn’t have a car (or even if she has one but can only afford to use it for essential trips), but she would probably appreciate the offer of an excursion of some nature. Don’t place it in the date category. Maybe a shopping expedition. Maybe invite her along to an event you’re “already” going to. A street fair. A nature walk. Whatever. The point is to expand the relationship without the pressure of a date. You can even push it a little further toward date by mentioning things you enjoy and seeing if she expresses interest (or getting her to mention things she enjoys and express your interest). Exhibits, bands, concerts, theater, or whatever—find something of mutual interest that is taking place somewhere she normally wouldn’t be able to get to and invite her along. Come up with the right thing and don’t use the date word and it’s almost a certainty.
So there it is. Whether you’re interested in a barista or a fellow customer, a coffee shop is a great place to make a serious connection. It allows for the repeated exposure that produces relationships, without the noise, distraction, and immediate time pressure of the bar scene. If you play it right, you’ll make your desired pick up—it just takes time.