Ask Bex

Ask Bex- Retail Rendezvous and Twitterpated Tweeting

Ask Bex

I have a crush on a barista at a café I frequent. He seems potentially interested in me – always remembers my name and my order, asks me how my day is going, and continues to make conversation with me even after I’ve ordered/paid/sat down – but I’m not sure if he’s just being friendly because it’s his job to be friendly. How do I make a move without making things awkward?

Sincerely yours,
Confused, Crushing & Caffeinated in Canada

Here’s the thing CCCiC, I’ve worked in customer service for over 8 years, and any sort of flirty dynamic between a service person and their customer is complicated. There’s an inherent power dynamic in your relationship, the person working is literally being paid to be nice to you (and, particularly in food service or sales environments, may be relying on being charming to get tips or sales) even if they don’t want to.

baristaI’d recommend starting by looking for your typical indicators of interest, which it seems like you’ve done already. The fact that he remembers you and goes out of his way to continue conversation well after he would be required to are all really good signs, but it’s still entirely possible that he’s just very good at his job. That said, he faces much higher risk by making a move than you do. If he asks you out he not only runs the risk of being turned down, but also of being accused of harassing a customer and being inappropriate. You run the risk of some embarrassment and maybe some cold coffee. If you want something to happen, you’re going to have to make the move.

Typically I don’t recommenced giving someone an “out” when you are asking them on a date (or asking them to do anything you want, frankly). It is read as insecure, and makes the person hearing it wonder if there is a reason they should decline- it puts the idea into their head. In this case though, it is important to make it easy for the person to decline, because they are in a situation where it may not feel safe to do so. Are you the kind of customer that will throw a fit at their job if they say no? Will you go to their boss saying they were rude? Service people are in a headspace where they are doing everything they can for a customer, and suddenly having to say “no” can be much more jarring than it would be in a different situation.

A simple “Hey, you seem cool, I’d like to give you my number, is that okay or is it against policy or something?” gives him a built in excuse, whether he’s not into you, nervous about the idea of dating customers, or it really is against policy. Now comes the really important part- if he does use that built in escape clause, don’t make it weird, casually accept it and move on. This is someone you’re going to see regularly and you don’t want them to cringe every time you walk through the door. Good luck!

What can I do to escalate things with a Twitter crush if we’ve never really been explicitly flirty or sexy in our communiqué? Is there a “chill” way to be like, “Hey, we should totally go for drinks sometime and/or have a whole bunch of sex”?!

Sincerely,
Touchy Tweeter in Toronto

The easiest way to navigate social media flirting is to think about it the same way you think about flirting at a party. You wouldn’t walk straight over to that cute stranger across the room, grab their arm, and drag them into a closet to speak alone. Likewise, don’t slide into the DMs of someone you’ve never met and expect to woo them right away, instead start engaging with them in more public mediums.

Reply to their tweets (not all of them please), send them things that will interest them (like, actually relevant things), make sure they actually respond and you’re not just spamming them and making them uncomfortable. Once you’ve become a positive presence in their public social media existence, you can comfortably move to their DMs.

Slide Into Your DMsA first DM should be relevant to your other conversation (and not blatantly sexy please) while still having a reason for moving private. Did you want to continue a long conversation that isn’t relevant to the public? Send a link to something they might find interesting (not porn), or ask a question that maybe didn’t need to be public (not a sex one!).

The thing about social media is it’s easy to feel like you’re much closer to someone that you are. If you follow me, but I don’t follow you, you might know all kinds of intimate details about my life while I barely recognize your name. You want to make sure the person is actually familiar with you before you just appear and start inviting them places. Social media isn’t deliberately made for dating, so most people, especially those socialized as women, need to establish a bit more trust before they go out with someone from Twitter than they might for someone from Tinder or OKC.

When you are finally ready to invite them out, invite them on a specific date, not just a vague “we should do a thing”. Saying “Hey! I saw you talking about Guardians of the Galaxy, want to go see it together?” tells the person exactly what to expect, and shows that you put some thought into what they’d actually like. If you’re feeling particularly bold, opening with “I’ve really enjoyed talking to you, I’d like to take you on a date” is a great way to make sure your intentions are known!

Have a question you’d like me to answer? Email me at BexTalksSex (at) gmail with “Advice” in the subject line and I’ll answer it in a future column!

About Bex

Bex talks about sex, a lot, and feels this is the only way to reduce the stigma and lack of education surrounding it. When they're not trying to save the world, talking about sex to strangers, typing frantically, or sticking things in various holes they are usually indulging the other facets of their geekery.

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