Conversation Questions

conversation questionsIf you’re looking for better ways to break the ice, learning some skillful conversation questions is where to start. Everybody loves to talk about themselves, and the more you can keep them talking, the less you have to worry about putting your foot in your mouth. If you want to become the one with the mojo when it comes to conversation, check out this course on How Communication Works. Whether you want to nab a date, impress the in-laws, or persuade the boss, being a conversational guru is where it’s at when it comes to getting ahead.

What to Ask

There’s never any harm to asking someone what they do for a living, where they grew up or what sorts of hobbies they enjoy. Those are all perfectly acceptable options, but if you want to get beyond the façade, try asking questions that are more revealing like:

  • “What are you reading these days?”
  • “Where in the world would you most like to visit?”

These questions give you a better opportunity for discovering if you and your date are on the same page when it comes to what you want out of life. Generally speaking, there are telling differences between peeps who read the New York Times and those who prefer the Wall Street Journal. Aim to find out what makes someone tick. If you’re in an online dating or speed-dating situation, make sure you’re the memorable one. Asking “What do you wish for when you wish on a star?” makes a way bigger impression than finding out who paid your date’s last paycheck. If you want to ace your next romantic encounter, try this five-star course from charisma coach Charlie Houpert. Charisma isn’t something you’re born with—it’s something you practice. Give yourself an edge for meeting people 24/7 by learning how to be awesome all day long

When asking questions, at an uncomfortable first meeting, the key is to make your companion feel more relaxed. If there’s an appropriate question that’s a quirky and fun, go there.

Consider these:

  • “What trophies did you earn as a kid?”
  • “What would be your perfect vacation?”
  • “What’s at the top of your bucket list (that is: things to do before you die)?
  • Law & Order or The Daily Show?”
  • “Who’s your favorite comedian?”
  • “Is vinyl really as good as all the hipsters think?”
  • “Are you into holistic health or modern medicine?”
  • “Miley Cyrus: Yay or nay?”
  • “What’s the first thing you would try to teach your children?”
  • “Are you a bargain hunter?”
  • “What sole possession would you take to a desert island?”
  • “Would you rather be on Survivor or Amazing Race?
  • “What would you choose for your last meal?”
  • “Do you have a favorite local restaurant?”
  • “Glamping or camping?”
  • “What’s the one thing you think is definitely worth the money?”
  • “Do you have a garden?”
  • “Modern artists: mind-bending masters or masters of hype?”
  • “Do you believe in talent or hard work?”
  • “In high school, I got voted Biggest Mooch. What were you?”

Yes, some are silly, but it’s all very telling. They key to being a good conversationalist is to make the people around you feel comfortable. That’s why you ask easy questions of opinion: there’s no wrong answer. Someone who loves twerking might not be right for you, but at least they won’t feel like you passed them up for not working at Google. On the whole, these types of questions don’t elicit judgment or censure, so it puts the person you’re conversing with at ease. And who wouldn’t want a second date with someone who makes them feel good?

What Not to Ask

For a literate, interesting person like yourself, it can be hard to stay away from political topics, but the old adage of never talking about money, religion and politics still rings true. It’s one thing to discuss an event like the sinking of the Concordia and another to discuss how you feel about Russian presence in Ukraine. At the same time, asking people about their future is great; asking about their past can be hazardous. “What’s your biggest regret?” forces your companion to remember a negative incident and they may end up associating you with those bad feelings. Help someone remember the positives and that halo effect may be just the break you need to get to second base. If you’ve got a difficult conversation you have to resolve, check out this course to help manage conflict before you get started


The difference between a pro communicator and an amateur is practice. The pros know that to succeed with your communication you need to prepare. Think of a list of questions that you can ask that are off the beaten path. “If you could have lunch with anyone, who would it be?” There’s a big difference between someone who wants to meet Angelina Jolie and someone who wants to meet Jonathan Franzen. Asking, “How would you spend your time, if you didn’t need to work?” will give you insight into someone’s dreams, aspirations and values. Whether preparing for a date or just trying to be a more interesting partner, asking those types of questions not only gives you more interesting answers, it makes you a more interesting companion. If that all feels too personal, try something like “How do you like to spend your Sunday?” As they say, actions speak louder than words. Getting someone to tell you what they do, or what they would do, is usually more reliable information than asking what they think. Your aim is to uncover habits, preferences, and values, without going overboard. “What’s your take on the death penalty?” isn’t where it’s at.

What to Respond

You know how you prep for an interview by preparing responses to possible questions? It may sound dorky, but canned responses are a great way to take the pressure off in a date-like situation too. Prepare a few stories that represent you well and you’ll be more likely more likely to make in-roads with your audience professional or otherwise. Of course, you should be able to answer any question you’ve posed to someone else. Even when your making small talk, try to be a story master by withholding some critical information until the end of your point. This keeps listeners captivated by what you’re saying. You don’t always have to end with a punch line or a twist, but if you can, you’ll be a lot more interesting to others. If you’re dating results have been slow, get the low down on how to talk to women with this course.

How to Say It

If you’ve ever fallen asleep in a lecture, you know that even the most scintillating content is a snooze with the wrong delivery. When you’re speaking, it’s not only what you say, but how you say it. A monotonous pitch will make you boring. You must vary your tone and inflection to keep listeners in tune. While you’re at it, make sure you’re speaking at an audible volume; soft speakers rarely command respect. If you think you’re voice has been holding you back, improve your delivery and confidence with this course for voice mastery.

At the end of the day, a conversation is about an exchange of ideas. Be open and candid about who you are and help the person across from you feel at ease. (If you want some tips for how to turn self-doubt into confidence, this course is for you.) Just remember, when you’re asking conversational questions, give your companion the one thing they can’t get anywhere else: YOU.