Entertainment Entertainment Dating

My barista gives my heart a caffeine jolt

Dear Anna,

I have a crush on the barista that works in the coffee shop near me. How can I convince her to go on a date with me? Aside from small talk and asking about Wi-Fi problems, I’m at a loss. —Cuppa Joe

Dear Joe,

You mean to tell me that you opened with a foolproof Wi-Fi connection pick-up line and she didn’t leap across the counter and into your lap? Are you sure she’s not a robot, like in the adorable family sitcom “Small Wonder” from the ’80s?

I’m just joshin’ ya, Joe. Talking to girls is hard, and talking to girls while they are supposed to be doing their jobs is even harder. But unless you can somehow segue from asking about why the Wi-Fi password is SparkleMonkey to asking about her hopes and dreams (who didn’t want to be a sparkle monkey when they grew up?), you might need to have a better follow-up question/conversation-starter ready.

Also, I am slightly concerned that you can’t keep a conversation going with this gal in the first place. It might speak to her disinterest, or mean that perhaps she has a boyfriend, doesn’t like boys in general or even that y’all just don’t have a rapport. But, on the off-chance that none of that is true and you simply are painfully shy, here’s my advice.

As we talked about recently (see “How to compliment a woman you’ve just met”), it’s best to engage a cute stranger by commenting on something she has control over, e.g. “That’s a wicked necklace/tattoo/scarf. Is there a story behind it?” Or “Do you choose the music? I love weeping about The Smiths at 8 a.m.” If you notice a particularly rude or memorable customer, you also could try empathizing or commenting about them.

If you’ve worked in the service industry, even better. Supply your own crazy tales of uppity or mean customers, to which she’ll probably relate and offer her own examples. My first job was waitressing at a retirement home (at the amazing rate of $5.25 an hour with no tips) and in the past I’ve regaled people with tales of being chased by an old man with a walker while he barked at me like a dog. That story hasn’t gotten me laid yet, but I remain hopeful.

After you’ve succeeded in some getting-to-know-you-type convos, you can move on to a more direct approach. “Hey, you seem like a cool girl and I’d love to hang out with you when you’re not obligated to wear that smock. What do you say?” Whatever you do, avoid cheesy lines about how she “perks you up” or is “hotter than a cappuccino,” which will not garner you any points. However, asking her if anyone has ever used a cheesy pick-up on her might also be a good conversation starter.

Good luck, Joe. Here’s hoping you have a steamy future.

For more on flirtation, see this previous column on how to tell if someone is flirting with you.

Want to ask Anna an anonymous question about love, sex or dating? Email your quandary to redeyedating@gmail.com. Need to give your dating life a boost? Sign up for RedEye Dating.

Copyright © 2015, RedEye
Related Content