Over time, I've spent a lot of time in coffee shops and have learned a lot about existing in that environment. What follows is a loose guide to connecting with people in that environment but, to some extent, this is also a guide to being friends with people. The short version? Minimize annoyances.
Initial- Feel free to try talking to coffee employees. Making coffee gets boring and opportunities to interface with others is usually welcome.
- Familiarity breeds trust so being present at roughly the same time of day/week can help.
- If necessary to create a bridge, tell SHORT jokes. I wouldn't lean on that as it can be a little off-putting.
- Learn names.
Walk away
- Pay attention to body language - for example, if they're not looking at you for more than 5 seconds, might be time to walk away.
- Verbal cues are also important. For example, it's okay to ask "how are you?" but if you get a flat, non-committal answer, maybe move along.
- Don't try talking to employees when there's a line, when someone looks like they might be walking up to order, or when they seem stressed out / annoyed.
- If one of the employees continually avoids you or doesn't say much to you, make sure you give them plenty of space. I've had some folks who just don't want to talk to me and that's okay.
Avoid
- Asking about tattoos or piercings, unless it's new. The only way to bring this up is after having known the individual. Expect the topic has been beaten to death for this person.
- Talking about the weather and traffic. They affect everyone but they also bore everyone. These topics have been exhausted.
- Reading name tags. Ideally, you should ask their name.
- Asking out employees unless you feel comfortable they are single and interested. Coffee employees tend to flirt with customers for tips, so you'll have to filter that behavior out as the best you can. Strange as it sounds, I've only ever heard of Baristas asking out with customers, not the other way around.
Ordering
- Ideally order drinks that are easy to make. If you ask for something a little harder, try to be gracious about it. Try to order the same thing or from a short list. Trust me that for some coffee shop employees, you will always be the "double decaf caramel" guy/gal and that's okay.
- It goes without saying but you should always tip. I try to aim for in the $1 range. Eventually you will start getting discounts on drinks, but this never *really* pays for itself.
- Feel free to tell someone if they made the drink and it was especially good.
Hanging out
- Busing tables (cleaning) a little bit can help. Dishes are usually the most boring part of the job so you can endear yourself by making their jobs easier.
- Other (very minor) maintenance tasks also help like cleaning up your own mess and fixing something that's broken.
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