Last time I pointed out how coffee shops are a perfect place to hit on the type of girl you want a relationship with.  Now the question is how you do that successfully.

For our purposes, there are two basic categories of women—customers and baristas (or counter girls—the difference is the same as between executive assistants and secretaries).  I’ll talk about them separately, but note that even if you’re not interested in picking up the barista, establishing friendly relations with one can help in the pursuit of a customer.  So tip—well.  And don’t be obnoxious—to her or to other customers.

Sometimes a girl is in the coffee shop by happenstance (meeting friends, passing by when the need for caffeine strikes, or whatever), but usually she’s there because it’s her coffee place.  She’s a regular.  She comes here for coffee because it’s near her home, or her work, or her school (or if you’re unlucky, her boyfriend). 

So you need to become a regular too (if you’re not already) and time your visits to coincide with hers—but not too closely.  Coming and going at the same time she does becomes obvious—and creepy.  So time your coffee stops to overlap with hers.  And by varying lengths.  Here’s where a friendly barista comes in handy. You can just ask when that interesting customer tends to come in, and if she already knows you’re a good guy she’ll be happy to tell you.  In fact, she might even provide helpful information about her.  Baristas can learn quite a lot about their regular customers—and not just their usual order.   (And we’re not above doing a little matchmaking ourselves, especially if a customer we like expresses interest in another customer we like.)

OK.  You know who you want to hit on and you know when she’ll be present.  Now, how do you do it?  Exactly what you say is up to you, but the basic type of comment depends on the location.  And no, the coffee shop is not the location.  There are several types of locations within the coffee shop and each requires its own approach.  And remember the point of all this is repeated exposure.  You want to “meet” her again and again (just not all on the same day), so arrange to encounter her in different locations.  This will also allow greater variety in what you can say so you’re not repeating the same inanities every time.

The first location—literally—is waiting in line.  Everybody does it.  Everybody hates it.  There’s a commonality about the experience that makes people vulnerable and willing to talk.  Also, while waiting, people are usually between things that occupy their attention.  If they know what they’re going to order (and in a coffee shop they usually do), they’re mentally on hold knowing they’re going to have to place their order at any minute and not wanting to start something else until they do.  So they’re willing to strike up a conversation with a stranger—especially if it’s a stranger they’ve actually seen before in the same place.

After getting their coffee, people usually go to the cream station, even if only to pick up a swizzle stick or a napkin.  So you can wander over there on minor business while she’s there.  Smile and say hi.  Be helpful if the opportunity arises—or ask for help. But don’t be overwhelming or too intrusive.  If you get her flustered and she uses the wrong sweetener, she’ll blame you—and she’ll have negative memory of you the next time you say hi.  The cream station is not the place for extended conversation.  Just remember the point is repetition; individual encounters can be brief, just enough to remind her you exist.

If she is sitting at the counter when you get your order, you can sit near her—close enough to talk, but not breathing down her neck.  The point is to make her feel comfortable, not uncomfortable.  And that means don’t change your seat if you’re there before her.  The exception is if you can give up your table to a group in need of space and move to single spot at the counter.  This not only puts you in her proximity, it makes you look like a good guy.  Make conversation as though you’re just passing time, not as if you’re trying to pick her up.  It’s more credible—and will eventually lead to picking her up!

The most difficult situation is if she chooses an outside table when you’re already settled inside.  Your moving outside is obvious and too blatant, especially for an early meeting.  If you’ve had previous encounters, then maybe you can pull it off—if you have a good pretext.  The best course is just to finish up before she does, then stop for a quick hi as you leave.  Again, repetition not length of encounter is the object.  It’s all laying the groundwork for chatting, then deeper conversation at later encounters.

More and more coffee shops have comfy chair sections—easy chairs, sofas, etc.  They provide a more comfortable, sort of house party atmosphere where it’s easier to strike up a conversation.  The problem is not to make it look too obvious in joining her there.  But if you’ve prepared the way with simple hellos and brief comments in other locations on other occasions, then it becomes a natural escalation of a growing relationship.

Next time I’ll consider the slightly different process if the barista herself is your target.