Free Association

If your mind goes blank, use a technique called free association to generate a response. These are words that immediately come to mind upon hearing something. For example, if someone talks about cats, practice free association with the provided exercises, and you’ll be able to come up with answers more quickly and easily. Conversation as a whole is just a series of interrelated responses and stories, so free association is practicing conversation flow.

Regardless of who you’re talking to, you’re likely to be asked the same set of generic questions. These include what do you do, how was your day, and others like these. You’ll want to have two separate answers prepared for such questions, one of which is interesting and unique (the layman explanation), while the other is more informative (the expert explanation). Being too esoteric upon first meeting someone isn’t always helpful, and can confuse and render others speechless.
Finally, learn to give good compliments. This is also deceptively easy. Compliment things that people have control over, or made a choice about. Don’t choose genetic qualities like height or eye color; instead choose things that people actively put effort into. People feel comfortable and flattered, and then start to open up.

Practice Free Association

There are times when it doesn’t really matter how good a speaker you are, or how interesting or engaging you might be as a person—or for that matter, how interesting and engaging the person you are speaking to is. Sometimes conversations just get stuck. It’s no one’s fault; it just happens.

We can get stuck in topics we don’t care about, or a conversation can turn into what feels like an interview, making it feel shallow and awkward. We might discover that we have very little in common with the other person. When we try to think of different things to talk about, it becomes difficult, like trying to climb out of a hole.

When we find ourselves in a conversation where we’re tangled up in a tough or impossible topic, we end up feeling frozen and trapped, which creates anxiety and frustration. The more we try to get out of the rut of the conversation, the more stuck we feel.

So let’s simplify conversation.

Conversation is a series of statements, stories, and questions. After one person contributes one of those elements, the other person responds in kind, either on the same exact topic, or a topic that is in some way related to the original one.

That’s where free association comes in. This is the practice wherein you say things that immediately come to mind when you hear something without trying to filter it in any way.

Isn’t conversation just a series of free-association exercises?

For example, if someone says something to the effect of, “I love cats soooo much!” and you know nothing about cats, you might find it difficult to contribute anything to the conversation. If you absolutely hate cats because a cat blinded your right eye when you were a child, this might just be a conversation killer, or it might launch you into a bitter rant that will also murder the conversation.

You might not have anything to say about cats, but what if you took away the statement and context and focused on the word and concept of cats?

With simple free association, you can find a way to quickly and efficiently breathe new life into the conversation, regardless of how deeply stuck it may feel.

Just free associate five things about cats. In other words, blurt out five things (nouns, locations, concepts, statements, feelings, words) that flashed into your brain when you heard the word “cats.” Allow your mind to go blank and zero in on the word “cats.” Stop thinking of the word “cats” as a trigger to past experiences and memory. Instead, start looking at it as a fresh concept unconnected to what you’ve experienced before. Play a word association game with yourself. What does “cats” make you think of? We’re just talking about purely intellectual connections.

It doesn’t matter what you feel, what your emotions are. It doesn’t matter what your experiences were, whether you were traumatized or not. It has nothing to do with that. This is just a purely intellectual challenge to try to rapidly fill out a list of what “cats” as a concept can be tied to.

For most people, when the word “cats” is mentioned, they think of kittens, cuddles, sand boxes, cheetahs, lions, fish, sushi, fur, dogs, allergies, the musical, etc. Keep in mind that there is no right or wrong answer here. It’s all free association. What’s important is that you’re rapidly filling out that list of things that you can intellectually connect with the word “cats.”

You’ll notice that doing this is much easier than coming up with a responsive statement or question to the declaration, “I love cats sooo much.” Yet, your task and challenge is exactly the same—where do you go with what the other person said? With that framework and perspective, it’s much easier to disassociate from the actual statement and free associate with the subject matter.

Doing this will train your brain to think outside the (cat) box, approach conversation in a non-linear way, and see the many possible directions one simple concept or word can take you.

For instance, you may respond to the statement, “I love cats sooo much” with any of the following replies:

“I’ve always wondered whether cats enjoy cuddle time as much as dogs seem to do.”

“Have you heard of these hypoallergenic cat breeds?”

“So would Cats, the Musical be something you’d enjoy watching?”

Now suppose that someone proclaimed their love for car racing, and suppose that you know nothing about that either. What are the top five or six free associations that come to mind for car racing?

For me, it’s a mixture of (1) NASCAR, (2) gas, (3) tires, (4) The Fast and the Furious movies, (5) Japan (don’t ask me), (6) Mustangs. Here’s the magic part—each of these six associations are perfectly normal topics to switch to that are still in the flow of the conversation.

“I love watching car racing! It’s so fun!”

“You mean like NASCAR, or illegal street racing?”

“I always wondered what kind of gas mileage those cars get.”

“Do those cars have specialized tires? I don’t think my car’s tires could take that!”

“So are The Fast and the Furious movies your favorites?”

“I heard they do some kind of drift racing in Japan—do you mean like that?”

“I always imagine car racing happens with huge, powerful Mustangs. Is that the kind of car races you watch?

Try free association with the words “coffee” and “trains” and think about how much easier it is to construct questions and generally converse about something once you can form a mental map of the subject and its related topics.

You just feel unstuck.

Of course, the best way to do this is not to try it the first time when you’re in an actual conversation. Free associating is the easy part, but utilizing the things that come to your mind in an ongoing conversation can sometimes be tricky. Practice free association consciously several times throughout the course of a week. The more you do it, the better you get at it.

Here’s how to practice: on a piece of paper, write five random words. They can be anything—a noun, verb, memory, or even an emotion or feeling. Suppose the first word you write is “napkin.” As quickly as possible, write three associations for that word. Take the last word you came up with, and then as quickly as possible, write three associations for that new word. Repeat three times, and then move to the next set of words.

Napkin -> table, spoon, fine dining.
Fine dining -> France, Michelin Star, butler.
Butler -> Jeeves, white gloves, Michael Jackson.
And so on.

Practicing free association is an excellent foundation for good conversation because conversation is about relating unrelated ideas, making connections, and going with the flow of topics. Next time you’re struggling for something to say, take a step back and tap into your previously practiced free-association skills.

Just as with anything else that has to do with conversation skills, you can only master it if you try it enough times. The best part of all this is that you can do it instantly. You get caught in a stream of consciousness flow. Always remember there is no right or wrong answer. If you believe there is, you’ll be putting unnecessary pressure on yourself.

In case you find yourself in a hole with the free-association technique for any reason, one alternative you can fall back on is to simply ask the other person to elaborate about what they said. So if someone claims to love cats or racing, nudge them to speak more about it. This will give you more material to work and free associate with. For example, common reasons for liking cats include them being cute and independent compared to dogs. If someone cites these reasons, you now have more things to free associate from—cats, cuteness, and independence. Use this abundance to come up with good responses. Flow achieved; silence averted.