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May 4, 2009
@ 1:00 pm
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My Most Awkward Conversation Ever

I have a friend, who we will call “A”.

“A” switched to a Mac after hearing me love mine, and loved it. I would routinely get text messages or emails talking about how much easier it was, etc.

“A” came over when I first purchased my iPhone and couldn’t wait to see it, and had talked about wanting to get one.

When the iPhone 3G was scheduled to come out, I was thinking of selling my original iPhone to replace it with a new one, and I wondered if “A” would be interested in buying it.

Here’s how the conversation went:

Me: “Hey, if I upgrade my iPhone I may be looking to sell mine. Would you be interested?”

A: “Sure, probably. Let me know.”

Me: “OK, will do.”

A: “I have a question for you.”

Me: “OK”

A: “If I get killed over in Iraq, will you be the one to tell my parents? I don’t want them getting the news from some Army representative.”

Did I mention that “A” is in the army? That’s probably an important thing to know.

Also important to know: I’ve never met A’s parents, and they live in Texas and I live up north.

But I don’t know if anyone has ever asked you that particular question before, but if they do, there’s no way to say “no” (not that I wanted to, except for a) the discomfort in the idea and b) did I mention I’d never met them before?)

If that isn’t the most awkward conversation I’ve ever had, it’s pretty close.

So. What’s yours?

  1. rachelarogers answered: confronting my former roommate about talking on the phone with and sending letters and stuff to my current boyfriend. Whole situation sucked.
  2. cleversimon answered: “Remember when I told you I was on birth control? I wasn’t.” “…”
  3. lidmo answered: Calling off my wedding at 22…
  4. inmi answered: Almost every conversation I have is at least marginally awkward, because I rock like that.
  5. stacey727 answered: Called a probationer to yell at for not being at school.He had just found his gmom(guardian)dead in bed.He hadn’t even called anyone yet.
  6. biorhythmist answered: Trying to explain how the toddler we were babysitting walked out the front door while my girlfriend and I were making out. Really.
  7. insooutso answered: I think your conversation might be my most awkward conversation.
  8. timestolen answered: Talk w/ my ex, who didn’t grow up where I did, told me he was dating a new woman who turned out to be my best friend friend from high school.
  9. talesofbeingtj posted this
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