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Meeting Someone For The Second Time Is The Most Awkward

Image by Snugg LePup

In two weeks, I’ll be heading to Utah for my company’s Grand Meetup, the one time a year when the entirety of Automattic meets in person (we’re a distributed company, so everyone works from home). This will be my second Grand Meetup, which means that I will already have met a significant percentage of the people who will be there.

Should be a great time, and definitely less pressure than the first Grand Meetup, right?

Mmmm, no.

Oh, it will be fun. Don’t get me wrong. At the same time, there are several things my over-thinking, over-analyzing mind will be freaking out about over the next… well, three weeks….

Last year, I mentioned that I’m an awkward hugger. A year later?

Yup, still awkward. So there’s that.

Now, for the record, I love meeting new people. I really do. I’m good at small talk, and I rarely have a problem engaging someone I just met in conversation. Sure, the hugging is awkward, but hey, that usually doesn’t figure into the first meeting, anyway (more on this in a minute).

Besides, I just let the other person initiate, and then the only thing I have to worry about is that people might think I’m stand-offish and don’t like to be touched. Well, better to be stand-offish than creepy-feely, if you ask me. (The photo above is totally staged, by the way, but it does represent my worst nightmare when I go in to hug someone.)

So yeah, meeting someone for the first time? Not a problem after all.

Now, you know what is a problem?

Meeting someone for the second time. That’s hard. And if you don’t think so, here’s why maybe you should worry about second meetings just a tad, too:

When you meet someone for the first time, you have everything in the world to talk about. Your relationship, whether professional, personal, or romantic, is essentially a blank state. You get a chance to fill that slate with all sorts of wondrous conversations.

And yeah, you rarely have to worry about hugging (assuming you’re an awkward hugger, like me). Handshakes are perfectly acceptable on the first meeting.

But when you meet someone for the second time?

Now, there are expectations (not the least of which is whether or not the other person has upgraded you to hugging level). Here’s a partial list of all the things that can take a turn for the disastrous when you meet someone for the second time:

And the list just goes on….

Am I way over-thinking this? Oh, definitely. But that doesn’t mean I won’t still commit some of the aforementioned second meeting faux pas. (Faux pases? Faux pi?) In fact, given the sheer number of one-on-one meetings I have coming up, odds are I will make at least one of these mistakes at least once during the meetup.

And as someone who prides himself on his social skills, I’m slightly saddened by this daunting inevitability.

Now, maybe you’ll understand why meeting someone for the second time will always be way more pressure than the first. Damned expectations.

If you’re an Automattician, and we see each other in two weeks… you know what?

Can we just agree beforehand that I’ll stand and wave at you indiscriminately from a distance? And you can come and say hi (and even hug me) if you so choose? I think that will be the least awkward for both of us.

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