Timing of your actions is critical to many aspects of your dating life in general and dating any woman specifically. Timing of your actions is as important on your first dates as it is even earlier - when you just met a girl and you are trying to have that first conversation with her to figure out whether you will be interested in each other. Being funny and using humor in an attractive way is just as much about when you say something as it is about what you are actually saying. Many dating advice sources encourage men to be funny and use humor to attract women. I couldn’t agree more – humor is important to attracting a woman on so many levels. But few of these dating guys tell guys when you should be using humor for maximum effect.
The timing of being funny with women is critical. When you meet a girl for the first time, you want to make sure that after you break the ice with whatever you said to start your conversation with her you establish through your conversation that you are an original and interesting person before you are being funny. You should not be funny right away before you established that you are smart and interesting first, unless the circumstances make it clear that being funny or sarcastic is appropriate (such as in cases where the woman you started talking to has been having a funny conversation with a friend, and you interjected or you both are in a mood that makes sense for both of you to be silly and crack jokes with each other right away).
You want to show your serious side first, and then say something witty/funny in a non-chalant way, when appropriate and relevant. This is because a joke from someone who has already established himself as a smart and interesting person would have much more impact that the same joke from someone who has been goofy and acting too much like a clown before that. If the woman you are talking to has a sharp sense of humor, she might just burst out laughing, not only because what you said was funny but also because it was so unexpected in the context of how you were speaking previously.
Imagine a woman complaining about her previous boyfriend and how she wasn’t happy with him at one point in your conversation with her. You first tell her seriously that she should not be upset about the break-up but instead should celebrate the fact that she has been liberated from a relationship that she didn’t enjoy all that much and that she should be excited about all the opportunities she now has meeting and dating better men. Then, she tells you that one of the reason she wasn’t happy with her ex was because he wasn’t big enough below the belt, and he was very insecure about it. Then, you respond with a totally serious face: “Well, you have to be happy and grateful with what you have. I am perfectly happy with my three inches. Sure, sometimes I can’t find it, but that’s what microscope and tweezers are for” or something silly like that. Or you could make a sad face and say “that’s funny, because I just broke up with my boyfriend too.” That should be very entertaining to any woman, except the most uptight ones, who can’t take any joke, let alone a sexual one.
There is probably no more impressive combination of qualities in a man’s personality that being able to be serious and interesting while also being able to inject humor into the same conversation in a witty and entertaining way. Just make sure that when you are being witty and funny, you also don’t forget to be smart and interesting, as the former without the latter might make you look goofy or even worse – a clown, and this is something you surely want to avoid.