Thursday, August 26, 2010

Advice: Sister set me up with a guy via email! Awkwardness ensues.

Pretty Gamer:

My sister has given my email address to a gentlemen that saw a picture of me at her apartment. They're very good friends and she's been trying to set us up for a while now. He emailed me a couple of days ago and I've been tearing my hair out trying to figure out what to say in these emails. It's really awkward and I have no idea if my emails are coming off as too brusque. I've tried to walk a fine line between informal and casual since we don't know each other well, should I ditch email and ask for his phone number instead? But if I do that, what if he same thing happens over the phone? I hate awkward silences.

-Socially awkward in Seattle


I think the first thing you should do is figure out exactly where the Awkward is coming from. Is it because you don't have enough information about the guy? You're embarrassed about being fixed up? You don't mention whether your sister had your permission to give this gentleman your email address. And at any rate, if they're "Very good friends and she's been trying to set us up for a while now" - shouldn't she have briefed you on this guy so you have something to chat about in email? And if not, good gravy what is she hiding? (Sorry, that's the paranoia in me surfacing.)

I also just realized that I'm answering your question with a question. =P Sorry about that.

There are three possibilities here:

  1. You're not interested but feel obligated to engage this gentleman because of your sister's involvement.
  2. You're sort of interested but have no idea how to proceed.
  3. You're interested and don't want to blow it.

And to answer your actual question - if you're more comfortable talking on the phone, you've got everything to gain by calling him instead. As far as the awkward silences, pump your sister for information about his hobbies and interests. People love to talk about themselves, so ask open ended questions such as "What do you like to do in your free time?" or "How did you end up in (city, industry)?" Email and online communication in general is difficult because there are no emotional cues aside from emoticons, which run the risk of being too cutesy or creepy depending on the context. It can be difficult to know exactly how to judge conversational flow and where to interject since additional vocal and tonal cues aren't there to guide you.

Lastly, don't rule out getting together in person to just hang out and get a vibe both on how you feel. First Thursday Seattle Art Walk is coming up Sept. 2nd, and ( whether you're into art is almost a non-issue; It's a public place, with plenty of room to cut the outing short or extend it into dinner. Plus, of course, art and people watching as built in topics of conversation. Hell, drag your sister along and make her bring someone else for her to talk to. That way it's a "group outing" and can help take the pressure (and Awkward) off.

Hey readers - what do YOU think Socially Awkward in Seattle should do? What would you do in this situation? Is it okay to take this interaction offline and *gasp* use the phone to actually talk to the guy?! Is this advice full of crap? Tell us in the comments!

You can submit your own questions in our handy advice form!

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