Women say it all the time: a sense of humor is a very desirable quality in a man. This gives hope to a lot of guys who aren’t confident in their looks, but are quick with words. The problem is that for most “funny” guys, their sense of humor is a defense mechanism. They’re insecure about trying to connect with women, so they keep things light and try to make a joke out of everything.  Don’t think that just because you’re making her laugh that you’re building any real connection. The more she laughs, the less she is focusing on romantic possibilities.   There is also a big difference between humor and wit. Humor is a hand grenade; wit is a sniper rifle. You want to demonstrate the latter quality instead of being the guy busting out joke after joke, or trying to be the life of the party. It’s better to pick your moments to make witty comments and observations.   If you possess a sharp sense of wit, you’ve got a great advantage with women. If not, the good news is that this is a skill that can be developed. The best way to do so is to listen and learn from your favorite comedians.

Notice the topics they riff on and the way they deliver their punch lines. Usually, the more “straight” their delivery is, the funnier they are. As you build yourself as a Mack and learn more about music, movies, books and current events, you will be able to make more clever observations about things.

Save the rapid-fire one-liners and raunchy stories for when you’re hanging with your buddies, and stay away from telling drawn-out jokes (i.e. “Three guys walk into a bar…”).  Just think of how uncomfortable it feels when someone you barely know starts telling a long-winded joke at a party: you’re all standing around waiting for the punch line, at which point you’re required to pretend it was hilarious, just to be polite. (Besides, the funniest pick up lines are usually the dirty or politically incorrect ones, which may offend her.)   Also, when you’re around women, don’t tell jokes at the expense of others. Don’t crack jokes about any of your buddies; not only is that being a lousy wingma, but it can create an awkward atmosphere. And if you’ve got a self-deprecating sense of humor, keep it in check. Your goal is to build yourself up in her eyes, not knock yourself down.

Remember that while the occasional well-timed line can make you look sharp and clever, your primary focus should be listening, guiding the conversation and strengthening the bridge. Really, one or two clever, funny comments are all it takes to show her you possess a sense of humor. No need to keep the jokes coming one after the next.