Here's a little mini-course on how to be funny:
First, go read "Comedy Writing Secrets" by Helizer. And while you're at it, watch some good stand up comedy routines like Chris Rock, Eddie Murphy and Robin Williams. Listen for how they use word play, double meanings, exaggeration, and misinterpretation to create humor.
It's time to get yourself a set of standard things that you say for some of the most common situations.
Here's a list of some that I use personally and how you can use them:
1. Whenever someone has an emotional response to something, say "How do you REALLY feel about it?" For instance, if a woman says "I just HATE it when people smoke around me!" say "How do you REALLY feel about it?" The sarcasm is that they've showed that they have VERY strong feelings, so the "How do you REALLY feel" creates a joke on them that they're overly emotional.
2. Say "Anyway" and look away quickly after making a wise crack. For instance, if someone says "That girl over there is ugly" say "Oh, I thought she was you-anyway" (look away quickly). The looking away and quick "Anyway" trying to get off the topic creates a funny moment.
3. Misinterpret what women say. Always listen for opportunities to misinterpret words like it. If you say "Let's go over to the bar to have a drink" and the woman says "Let's do it," turn to her and say "Let's do it? You mean right here? I think the line for a bathroom stall is too long, and I'd rather have a drink."
4. Look for sexual innuendo in everything, and use it to accuse her of trying to seduce you before you even know her. If she says "Well, I'm getting tired, and I think it's time for bed" say "Bed? I mean, I don't even know if you know how to kiss... and you're trying to get me into bed? What happened to the old days where you could make friends first?"
5. Exaggerate. If a woman walks by that's overweight, say "What would you guess? 900 pounds?" Or if a woman complains about part of her body or her clothing (I love these opportunities)
exaggerate it. For instance, she says "My hair looks like hell today" you say "I didn't want to say anything." Ohhhh this is funny stuff. You'll usually get a hit on the arm (for which you can spank her on the ass). Then you can go on all night making fun of her hair, talking about how everyone is looking at it, how you're embarrassed to be seen with her because of it, etc.
6. Connect things around you current affairs in a funny way. If a woman with a huge butt walks by say "Hey, Jennifer Lopez is in the house." If a woman starts talking about how she just bought herself a new car, say "I like the effect that the Independent Woman song is having on you." (These are, of course, currently funny. Next year it will be a different set of things)
7. Don't smile too much, and don't laugh at your own jokes very often. When you smile or laugh, it releases the tension. If you can keep a straight face, the joke stays funnier longer.
OK, there's a list of basic things that I've learned about how to be funny. I'd recommend that you start studying humor, read books about it, go to comedy clubs, and learn more advanced skills.
Also, start reading Maxim and Stuff magazines. Read how they always use reversal humor. This is some good funny stuff.
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