Whoa, that's awkward.

You know those people who can go up to anyone, strike up an interesting conversation, and become really good friends within a few minutes? I am so not one of those people. Instead, I opt for the really awkward conversations. When starting a lifelong friendship, there’s nothing as effective as an awkward conversation. I find that the weather provides ample conversation starters for those lifelong friendship endeavors.

Me: Hi, it’s been pretty cold lately.
Person: Yep
Me: It wasn’t as cold last week.
Person: Yep
Me: Did you know that it rained twelve times in Portland yesterday?
Person: Only twelve?

See how interesting that is? It’s moments like those that make me proud of my ability to start conversations.

Here’s a conversation I recently had:

Me: Hi, my name is Ryan, my sister, (her name), gave me your phone number a few months ago. She said she’d gotten it from you and said I should call you, so I finally am.
Her: (repeated my sister’s name)? I don’t know anyone by that name.
Me: Uh…
Me: Well, this is awkward.
Her: haha!
Me: You met her when you were home from school for the summer…
Her: OH! Yeah I know who you’re talking about now.
Me: ha! I guess that’s what happens when you get a phone number and wait a few months to call.
….later in the conversation…
Me: Would you like to go have more awkward conversations in person, this Saturday, over ice cream?
Her: I have a boyfriend.
Me: Oh right, haha. Well then. This is another one of those things that happens when you wait several months to call someone after getting their number.
Her: haha, yeah. We could still be friends though.
Me: Right, do you or your boyfriend like to dance? (note: what on earth was I doing? asking them both on a date?!)
Her: I pretty much avoid dancing at all costs.
Me: Oh, I’m pretty much the opposite.
Her: Well it was really nice to meet you, I’m flattered you called.
Me: Yep, well nice to meet you too.
Her: bye
Me: bye

I learned/re-learned a few things from this conversation:

  • Acknowledging any awkwardness makes it funny and gets rid of it
  • She seemed genuinely impressed/pleased that I'd called. I had no reason to feel awkward. Well, except that whole "I waited 2 months to call her" thing.
"It's easy to regret your awkward conversations but hard to regret the ones you didn't have." - xkcd (quote comes from the title text when you hover over the comic)

Even though I have a lot of awkward conversations I’d much rather have them than no conversations at all. They don’t always work out, but they’re worth it either way.

What’s an awkward conversation you had? Did anything come of it?

Conversations, Awkward


  1. Manda Yo, bro!! What?? I’m glad you finally called her… ummm… I’m sorry you didn’t do it sooner and that she had a boyfriend. Ummm… her mom didn’t ever mention that to me. Awkward.
  2. Ryan haha, yeah I did. I thought I’d told you. I guess I didn’t! No big deal, it was my own fault for waiting for so long.
  3. kerflop You, my dear, can find the hidden silver lining in ANYTHING. I’d be too busy dying of mortification to “learn” anything from an embarassing situation. (see: the time I mooned the fed ex guy)
  4. Ryan

    ha! Dying of mortification is justified in the fed ex case. I’m not sure anyone could find any silver lining in that!

    Then again, if he wasn’t already married with children, he probably gained an appreciation for what women go through while raising kids . I suppose that could be useful to him in the future… as long as it doesn’t keep him from getting married in the first place.

  5. Beth Hey - you’re blog is all different now. I can’t find my way around! ;)
  6. Beth I really do know that I should’ve written “your” and not “you’re” but I have two excuses:
    1. It’s monday 2. I went to Bingham
  7. Ryan

    Both excuses are completely valid, so I’ll let you off the hook…

    … this time.