The Single Guy vs. the Awkward Email

The Single Guy vs the Awkward Email - AwkwardWe can all agree that it’s awkward when someone wants to set us up, right? Which is more awkward: to be set up with someone locally? or to be set up with someone on the other side of the state?

About a week ago, a coworker began telling me all of the wonderful qualities possessed by a friend of hers who lives in Richmond. “You really should email her!” she said as she handed me a Post-It with her friend’s address.

Now, I’m always curious about what leads matchmakers to believe that there will be a love connection between any two people. Being a cynic, I’m apt to think that they simply see two single people, assume they’re miserable due to their lack of relationship statuses, and maneuver those two like chess pieces until they join together like drops of water. I’m sure that’s not how people really operate. Most of the time. But what makes this coworker think that I’ll be a good match for her friend? Sure, we’ve worked for the same company for a couple of years, but I’ve only been working directly with her on a daily basis for a month. What does she even know about me?The Single Guy vs the Awkward Email - You Don't Know MeCome to think on it, it’s probably been over a week since I got this girl’s email address. I haven’t emailed her yet. I’ve been in local set up situations a number of times. It’s always uncomfortable. I can’t imagine, as a stranger, how one begins an email to another stranger. I mean, I’ve emailed people I don’t know before, but there’s been a clearly defined purpose for those emails. Those emails involved work or writing projects or complaining to Time-Warner Cable about all the things. But in this situation, I feel pressured by my coworker to generate a You’ve Got Mail style relationship out of nothingness. I can’t generate relationships with people I see face-to-face. She really needs to lower her expectations of me.The Single Guy vs the Awkward Email - Lower ExpectationsSo what should I say in this hypothetical email that will clearly never happen? I’m really asking here. Imagine the scene in A Knight’s Tale where William has input from his entire entourage as Chaucer writes a letter to Jocelyn. Except I don’t want an initial email to some woman that I’ll likely never meet to sound anything resembling romantic.

Here’s what I’ve got so far…

Dear Stranger,

It has come to my attention that you and my coworker have been talking about me behind my back. Who do you think you are? You don’t know me! How dare you?! How would you like it if I looked up your Facebook profile and started laughing at your status updates? Hurts, doesn’t it?


The Single Guy

Granted, I’m generally hoping for a good laugh with most of my status updates. Like this morning, I said, “I think the mistake that a lot of parents make is in not showing their children the movie Labyrinth and instilling a solid belief that, if they misbehave too much, the Goblin King will actually come and take them away and force them to listen to David Bowie music all the time.” Ha! That’s a good one. And maybe my email comes across as mildly antagonistic. But if any of you have better ideas, I’m all ears.The Single Guy vs the Awkward Email - You've Got Mail


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