At the age of 18, I decided to change my life. I had no friends, no close relationships, and life was unfulfilling. I went to the library in the self-help section and read as much as I could about social skills. One of the topics that showed up across many books was open-ended questions.

Conversation, to those who are socially inept like I was at 18, may seem like an impossible task at times. There are so many things to consider: How do you start them? How do you keep them going? What do you talk about? How do you transition from conversation to making a friend?

We can’t cover conversation in one article, but we can cover a very important concept: ask open-ended questions.

Why ask questions?

Questions are important in conversations because they lead to responses from the other person. You could simply make full statements one after the other, but it may mean the other person never feels like they are part of the conversation, but rather, more of a lecture.

Questions can also be useful because you can make a question about the person’s life, beliefs, religion, or interests, and that shows your interest in them, which usually leads to them feeling warmer to you.

Open-Ended vs Yes/No Questions

There are two types of questions: open-ended and yes/no.

A yes/no question is when the answer to your question is yes or no.

Examples: Do you like cooking? Did you watch the movie Avatar?

An open-ended question is when the answer to your question requires more talking.

Examples: What dishes do you like to cook? What did you think of the movie Avatar?

With a simple modification of the questions, we can turn them from yes/no to open-ended. More importantly, we’ve created a much more solid foundation for a conversation by inviting the person to add more to the conversation than a simple, one word answer.

The best followup questions: WHY? HOW?

Once you’ve asked the open-ended question and have gotten a fair response, you can easily follow it up with another question including a why or a how.

Why and how are both important words. The reason is that why and how, in many cases, will look deeper into the answer and possibly, into the person answering.


“Do you enjoy cooking?”

“What types of dishes do you like to cook?”
“I love to make Chinese food.”

“Why is that?”
“I studied in Beijing for a semester. While I was there, I met some Chinese students who taught me how to cook dishes from their hometowns. I loved the smells, the flavors, and I loved how delicious the vegetables tasted, which is important because I’m vegetarian.”

The beauty of how and why is that you can continue the conversation and possibly have a person reveal some interesting information about themself. In the above, we learned several things: this person studied in China and they learned how to cook from Chinese friends. They’re also a vegetarian. Not everyone will share so many details, but when do, not only are you developing rapport, but you now have several tangents you can lead the conversation toward. Do you want to talk more about food? Do you want to talk about traveling and studying in China? Do you want to talk about vegetarianism? Welcome to the wonderful world of generating conversation.

Yes/No questions are like open-ended questions to talkative people

If you are socially inept, you will be glad to be talking with talkative people. They will carry the conversation. They will often share things about their lives openly. And they treat your yes/no questions like open-ended questions.


“Do you like cooking, Janice?”
“Oh my goodness, I looooove cooking! Just last week, my boyfriend and I made this beautiful stew that his grandmother gave him the recipe for. It was delicious and the recipe had just the perfect mix of herbs and vegetables.”

Recognize talkative people and when you do talk to them, understand that they’ll talk more than you will. Just inject questions whenever there’s a pause or answer when they ask you a question. Talkative people love talking, and they’ll like it that you’re listening to them talk! These are the same people that will say “you’re a great listener” even though you might be day dreaming during the conversation.

Open-ended questions are like yes/no questions to people that don’t talk much

At the opposite end of the spectrum is the person that doesn’t talk much who you’ll run into here and there. Whether they’re tired, introverted, shy, socially inept or simply not interested in talking with you, you’ll realize that this type of person will be difficult to talk to, for you as a person with subpar social skills.


“Do you like cooking, Dustin?”

“Why is that?”
“I just don’t”

“Do you have hobbies then?”
“Video games”

“What’s your favorite video game?”
“Super Mario Brothers”

The above actually sounds much like how my conversations were when I was young and people tried talking to me. Actually, they weren’t so much conversations as they were interrogations. That’s a harsh word, but that’s exactly how conversations seem like when you run into a person that only gives one word answers does nothing to add to the conversation. And if you are guilty of the above, then make more of an effort! Elaborate! Ask the same questions back!

As a person who is developing their social skills, I would recommend that you stay clear of these types of people. You want to practice social skills with people who have normal social lives to get to a par-level of social skill. You cannot get there by having limited conversations with people with subpar social skills. Two wrong don’t make a right and two socially inept do not make a social butterfly. Trust me: as you develop your social skills and become more comfortable in social situations, you will one day look back and run into a socially inept person and think “Wow, work on your social skills, bro! Try an open-ended question!”