The Benefits of Being Witty

Can you conversationally think on the fly?

Can you make jokes that play off the conversation, what others are saying, and what some others are feeling, in the moment?

Yes? Good stuff.

No? Then you need to practice talking with people in which there is a felt tension at play.

Wittiness and its emergence often arises in times when there is a playful tension, in which your status is tacitly being challenged - but in a fun, social way.

If you cold-approach a girl, and your "worth" is being tested (since she does not know you, she will test this “worth” to gauge if she is interested and attracted to you), it helps to be witty in real-time about the conversation you're having.

Can you joke about what's happening in the conversation? 

Can you tie elements of the interaction together in a playful, interesting and funny way?

Can you playfully "one-up" this situation of playful tension - be it a person that's challenging you, or the interaction as a whole?

If a guy is playfully challenging your status in the room, to determine where you stand socially and how you feel about yourself, can you, likewise, reciprocally, playfully one-up the fun and yet interesting tension of the situation?

If you can, it disarms people and allows them to endear themselves to you.

Think of a great stand-up comedian or talk-show host at their best - how they play off the conversation with their guest and the vibe of the crowd. They are at their best when they playfully say the roughly perfect thing that breaks the tension - causing the crowd, and sometimes guest, to reflexively laugh. 

What they say (when they do it well) cannot be contrived, nor can it be too try-hard.

Rather, it needs to be fun-natured, relatively natural (not overly planned out or robotic), relevant, and playful (not something that comes from the ego or is somehow personal).

There are exceptions to some of the things I say of course -  for example, a stand-up comedian can indeed take a heckler personally and say something funny to one-up that scenario with wit - however, most of the time, the stand-up comedian is the most enjoyable, funny and witty when he does not take the heckler personally. The crowd (or people if you’re in a social scenario or picking up women) enjoy the person when he is playful and fun with his wit, not upset, angry, in his head, etc.

For example - Look at how Bill Maher handles the tension building in this interview - starting at 49 second mark (if you want to watch the tension build a little, you can tune in before that):


And look at how Jerry Seinfeld handles the audience during The Tonight Show’s Q&A Break ^ 

See them work off the point of focus (the conversation/interaction), intuitively calculating the observations and feelings of the guest and/or the crowd, and saying something witty to break the tension (all in real-time)?

In the real, social world, you can also cultivate this ability.

It is an incredible skill that can be cultivated through the general practice of socializing and also picking up women.

[Note: Women, I believe, are the reason that this also works in the general practice of socializing - male wit is intrinsically tied to male-female components of social interactions, even if women are not present. Indeed, I think that men who care about sex are constantly adjusting their social perspectives and behaviors, angling these behaviors in order to gain greater attraction from women).

However - paradoxically, as are much things which are in the world of socializing and meeting women - wittiness cannot truly emerge, function and be useful if one has an agenda, is not having fun, is thoughtfully calculating,  or is "in his head". One can only truly be witty when he is letting go, having fun and enjoying the moment. So, despite this observation, it does not necessarily help in becoming a witty person - it is just interesting.]

It takes time to cultivate an intuitive sense for when to be witty and how to be good at being witty.

Some are born with greater innate wittiness than others, however anyone, including you, can become vastly more witty than the majority of people you come across, should you consistently practice socializing and meeting women.

So, the moral of the story is - being witty is really fun, enjoyable, allows you to connect to others - and is also practical. You can become witty too, no matter who you are, provided you go out there and truly practice socializing and meeting women on a consistent basis.

Get out there!!