I’m guessing that if you’re reading this article you don’t think you’re a very funny person. There’s no shame in that. In fact, there’s nothing worse than a person who thinks they’re hilarious when they actually not. So, I applaud you for seeking help and advice. The first step is to always admit that you have a problem. Luckily, in this case your problem can be cured with a couple easy steps. I’m here to help you out in the best way that I can. I’m no hilarious ladies’ man myself, but I can usually hold my own in the funny department.
First of all, you need to chill out. Relax. Deep breaths. The number one problem that people have who are worried about being funny around women is that they get nervous and uptight. I’ve never seen a nervous and stressed person be deliberately funny. I’ve seen them get laughed at (or worse, subtly ignored) but never laughed with. It’s hard to be funny if you’re trying to hard to be funny. So, first things first, lets just take a step back and gain some perspective. You won’t be funny all the time and not everybody will always think you’re funny. It’s not the end of the world if you bomb in an attempt to be funny. You just learn from the situation (heck, your failure in itself might be a funny story to tell some day) and you move on.
Now that you’re nice and relaxed, the next step is to start paying attention to the world around you more carefully. We live in a hilarious world. I mean, have you ever SEEN a platypus? Or a two year old eat pudding? It’s your job to learn how to become an astute observer of the events that unfold around you and to you. This is the mine from which you will be extracting humorous nuggets. No longer will you be trying to tell set-piece jokes you read on the Internet or knock-knock jokes you learned in elementary school. Instead, you’re going to elevate your humor game to subtle observational humor. That’s the kind that’s easiest to naturally work into conversations. Nothing is funnier than the person who isn’t trying to be overtly funnier. And nothing is less funny than the guy telling a joke he read on a website.
Now that you are full of amusing observations about your own life and the things you’ve seen, it’s time to start working then naturally into conversations. You have to stay relaxed and you have to wait for the right time to drop your little nugget of hilarity. That’s why the more observant you are and therefore the greater library of potentially funny asides or interjections you can make the better off you will be.
A possible strategy is to have a couple funny stories ready to go that you could possibly relate to the conversation. Sometimes it can be tough to be subtly funny and having a good story ready to go can be a life saver. However, you have to be careful. First, you have to be sure it’s actually funny. Nothing is worse than listening to a long story that’s supposed to be funny but isn’t. Second, you have to make sure that you never repeat the same story twice to the same person (unless you’re married to that person, and then you can do it as many times as you want).
My last piece of advice is a word of caution. Avoid relying on sarcasm too much. Many people think that sarcasm and funny are the same thing. They’re not. Occasionally sarcasm can be funny, but not if its overused. The truly funny person makes funny and true observations of the world around him.