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…
Her: …
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?