Challenge

(minimum 45 minutes) -Begin interactions with "Hi, I'm (your name), I saw you and I wanted to introduce myself.” -You may also use a more direct approach and say, “Hey, I thought you were cute and I had to say hi.” -Each day, you must engage in one conversation that lasts for at least two minutes. (You can estimate the time, but it would be preferable to use a stopwatch or timer.) -Each day at home. Practice the provided free association exercise for at least 5 minutes.

Exercise: Complete a sentence out-loud, then create a new and unrelated sentence using a word from the previous sentence. (You can do this in writing if you prefer)

Example: 1. The universe has existed for billions of years. 2. I am 25 years old today, that’s half way to fifty. 3. Half of marriages end in divorce. 4. Marriage is known to be a cultural universal, which is weird because I heard that monogamy wasn’t natural.

Make sure not to tell a story, if you do, the exercise won’t be building your free association skills. Each sentence must use a word from the previous sentence, but in a new context, not to continue the previous thought.

Explanation

Striking up a conversation with a stranger can be anxiety provoking, keeping it going can seem even more difficult. Small talk like, “Nice weather, eh?” or, “Did you see the game?”, usually goes nowhere. So, how can you keep the conversation going?

If you were to analyze a good conversation you had with a friend, you would notice it was not a logical exchange of information, but something more like a free-association exercise.

Practicing the provided exercise will help you to make these kinds of creative connections naturally in all of your conversations. Not only will you be more engaging in conversations with women you meet, but more engaging in general.

Do not force yourself to free associate in conversations, as you practice this exercise you will start to do so automatically. Trying to force this is like trying to be funny on command, it’s ineffective, and can even be awkward.

If you are in a conversation but you are not naturally free associating, it’s okay to use a crutch to keep the conversation going. Memorize these basic questions so that you can maintain a conversation even if you can’t think of anything to say: What do you do? Are you from here? What are you up to today? What are you passionate about?

Based on her responses you can ask her further questions to deepen the conversation and get out of surface level talk.

Example:

You: What do you do? Her: I work as a waitress, but I'm going to school for business. You: What made you interested in business? Her: It's always been something I really wanted to do, I don't really know why, but it's always been a passion of mine. You: That’s cool, do you have a particular type of business you wanted to work in? Do you want to be a business owner or something else? Her: I've always wanted to run a non-profit that does something good for the world. You: What are some non-profits that you think are good examples of businesses that are doing something similar to what you would like to do? Her: .... (and so on)

Even if you can’t think of follow up questions to the four you memorize, the four questions should still lead to a two-minute conversation.

At first this challenge may be uncomfortable, and you might feel like you have nothing to say. But each day that you push yourself through this, talking to strangers will become more natural until you get to the point where having engaging and meaningful conversations with people you’ve just met becomes effortless.

Do this for at least 1 week and notice your conversational skills improve significantly.

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