There’s this guy at work that I like. He gave me his number and I gave him mine, but I don’t know how to start off the first message. Should I say “hey it me form work” or something else?

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Pushing through awkwardness used to be a skill that only guys ever really had to develop. And the ones that developed it would always have an advantage over those who chose not to.

But now it’s time to democratize all the social skills! You too can now feel what it’s like to communicate with others before it feels ‘safe’. And lots of times, it won’t be safe! Anything you say can and will be judged! Isn’t this fun?

The basic idea that I use is, if I have time to sit and think about it, always provide ‘safe ground’ to retreat back to. Safe ground is a convenient fiction that provides a surface ‘reason’ for why you two are talking to each other. We will call this a ‘conceit’.

If the conversation turns awkward, let’s say he gets inappropriately sexual too soon, or you start oversharing your band camp experiences, either one of you can simply refer back to the conceit, the nominal reason you guys are talking, and that’s usually the cue to exit stage left.

Think of the conceit as the ‘safe word’ for the dangerous consent minefield of taking an interaction outside of its usual context. As you both get comfortable with this Brave New World of not having the bumper rails of the workplace keeping you both in line, you can concern yourself less with safety and more on relaxing and having fun.

I don’t know if you remember that whole pick-up artist scene, but it used to be a thing that if a guy saw a lady he was interested in, he’d just walk up to her and strike up a conversation! IT’S SUPER AWKWARD!!!! Take everything about this particular situation, calling someone you already know from work, and turn it up to like 37. The quality of the conceit you provide is often a make-or-break factor. Just having the ability to say, “oh hey I gotta get back to shopping for my grandma, ya the one with Alzheimers, did she like frosted shredded wheat, I can’t remember, nice to meet you!” is the only thing keeping you from falling apart into a puddle of mush. Of course it never comes out that smooth until and unless you practice in a mirror like fifty-three times. Not that I ever counted or anything.

So I’d go with something simple like a question you have about something. If you’re feeling froggy, ask him for help with some small thing, nothing like helping a young lady out to get his ego moving. Bonus is you get to catch a little glimpse of how traditional he might be. He might start raising red flags right away, or you might have to dig them out of him.

You can step out on a limb and go purely personal, or you can play it safe and refer back to work. But basically speaking, you start the conversation to accomplish this one thing, then when you’ve gotten the matter out of the way, the conversation ends, and you come up with another reason the next time you reach out, until you’re both puking your guts out together after drinking way too much and trying out those scooter things you’ve both heard about but don’t live close enough to the city to try.