Usually I say to always go for the joke. It's worth looking a little ridiculous if it's funny enough. However, there are a few exceptions.
1. When jokes cost money. Just like my friend's "I can't afford a $4000 joke" couch, sometimes jokes cost money, and spending that money is not worth the 30 seconds of laughter. There have been many a times when I wanted to purchase a book for someone as a joke. And not just a joke book, but a book that served as a joke. But then I think it through and realize I'd be spending $15 to $20 on a book, and then I'd have to wrap it, and wait for the person to open it. We'd have a good old laugh when they opened up, and then what?" First of all, I probably don't have another gift because I spent the alloted money on the joke. Second, now he has a book that just takes up room on his bookcase, and he has to explain to every person who sees it "Oh, it was a joke."
2. When jokes make you sound stupid. Sometimes I do this just for my own amusement. I ask the obvious, stupid question, because I think it's funny. When with people I know, they can see the look in my eye, and they don't answer. They let me have the moment. However, you can't pull this joke when you're not live or with people you don't know. Mary made this point just a few minutes ago when she wanted to tweet "It's funny Harry Houdini is trending. Did he just die?" Now, I know that's a pretty funny joke. But others might just assume she's a fucking idiot. She's not. It's not always worth making the joke when you have to spend the rest of the day defending it. Unless it's a really awesome joke.
Another joke related topic I was discussing with my friend Tootie was about overhearing other people's conversations. I was thinking about how often we overhear a snippet and roll our eyes at how dumb other people's conversations are. And then I worry about when they overhear my conversations. And I analyzed our particular brand of conversation, and how we often have flat out ironic conversations. An outsider wouldn't really know we don't actually feel that way about the topic. We aren't letting on with our words; instead we mean almost the exact opposite of what we're saying. We know it, but passers by wouldn't. Then I thought "what if I'm jumping to the conclusion that these other conversations are dumb too quickly. What if they're also having ironic conversations?" Tootie stared at me. "You don't think other people have ironic conversations?" No. She doesn't think other people have ironic conversations.
I'm not going to stop having them though, because to me, that joke is always worth it. Really, it's just the $4000 joke couch that might be out of reach. However, if I ever become really rich, then I will resume my belief that the joke is always worth it.
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