You'll Never Guess (Really).

I'm pretty bad at conversation to begin with, so I really hate when people make it even more difficult for me. There are a few ways to make conversation harder with me. One of them is to put a sock in my mouth and cover it with duct tape. Alternatively, you can have a really exciting piece of news, and say "guess what!" Here's how conversations where someone tells me to "guess what" normally turn out...

Friend: Hey Brendan, guess what!
Me: You were molested as a child. I am the first person you've ever said anything to. Oh my God, it makes so much sense why I've never heard you speak of your step-dad before. Ok, your turn to guess what!

Friend: Um... No. I was going to say I have an extra ticket to a movie and was going to invite you, but now I feel sort of uncomfortable doing that. Also, I was never molested. And I've never mentioned my step dad because my parents are both alive and still married.

Me: Oh. Well, in case you were wondering, you were supposed to guess that I'm all out of clean boxer shorts as of yesterday.

But really, "guess what" is a pretty useless phrase, and only serves to sidetrack conversations. There's almost no way the person who is supposed to "guess what" could possibly add to the conversation. Also, what would happen if the person actually did "guess what?" Conversation would come to a screeching halt. Let's re-imagine that first conversation.

Friend: Hey Brendan, guess what!
Me: You were molested as a child. I am the first person you've ever said anything to. Oh my God, it makes so much sense why I've never heard you speak of your step-dad before. Ok, your turn to guess what!
Friend: Um. Yeah. That made this conversation easier. And judging by the way you're walking gingerly, I guess you're all out of clean boxer shorts. Was I right?

Me: Yup. Good talking, friend! See you!

See? The person who says "guess what" really doesn't want you to guess what. That would spoil the surprise. He just wants to create some tension. In that case, why not just say, "Hey, something exciting came up. Would you like to hear it?" Probably because that would be too easy and straightforwards.

There are other variations on this theme. One of them is "Guess who I just saw!" Sure, I'll try to guess who you just saw. Let me look around for a mutual friend, first. Then, if I see that mutual friend, I'll say his or her name. That way, I know I have a chance of being right, even if that's not who my conversation partner had in mind.

Friend: Hey, guess who I just saw!
Me: Did you see Chester on the sidewalk five seconds ago? Because I just did!
Friend: Oh. Um, yeah. I did just see him. I actually meant that I just saw Elvis, and he winked at me!

Me: Oh. Well, did you ask Chester about the cut on his face? It's a good story.

My personal (least) favorite is when people say "You'll never guess what..." Of course I'll never guess what! You could have done any number of things! But I could probably guess what you didn't do. That sounds like a way more fun game for me. "I'll bet you didn't just get laid, you annoying twerp," I would reply. But no, I could probably guess what if you gave me more hints though. I don't know about you, but life isn't a huge game of 20 questions to me. If you really want me to guess, you need to be more helpful in telling me what I won't guess. Maybe tell me something like, "You'll never guess how much money I found in my jacket pocket from last year!" That would be more fun for all of us.

Fortunately, there is a solution to this. The trick is the same as the fortune-cookie game. Just add "in bed" to whatever your conversation partner asks you to guess.
Eg.

Friend: Guess who I just saw!
Me: In bed?
Now I'm interested. Was it as good as I would imagine?

Friend: Guess what I just did!

Me: In bed? Ooooooh.

TMI if it's a guy. If it's a girl, I'm really interested.

Friend: You'll never guess where I was.
Me: In bed? Do I want to know?
I do guess that you are a slut, though! Bonus points?

So keep that trick in mind. If we are all obnoxious together, hopefully, everyone will stop using the phrase "guess what." But really, does this bother anyone else as much as it bothers me? Please let me know so I can tell if I'm really neurotic or not. Hope all is well!