Conversation tips: Ask these 5 questions

conversation, Asian man and woman sharing meal and talking

Have there been times in your life when you immediately felt at ease when talking to someone, especially someone you were meeting for the first time? On the contrary, can you recall a time when you felt awkward or uncomfortable in a similar situation? What was the difference between the two experiences? Sometimes, it’s difficult to keep the momentum going. After the “It’s nice to meet you” part, someone usually asks “So, what do you do for a living?” Once that’s cleared up, then what? This is where things get tough. Mastering the art of conversation will be easier if you keep five questions in mind. Asking any one of these questions can help spark interest and curiosity, and can also make the other person want to keep conversing with you.

Ask these five questions to keep a conversation going:

  1. What do you like to do for fun?
  2. What’s the best thing that happened to you this year?
  3. Is there anything special you’re looking forward to these days?
  4. What is one of your all-time favorite movies/books/songs?
  5. Who is someone you greatly admire?

Let’s take a look at each of these convo prompts

conversation, man holding book witting with woman wearing wine-colored cardigan and white scarf, trees in background

“What do you like to do for fun?” gives the other person a lot of wiggle room. An answer might be concise and to the point, such as “I like to go hiking”. On the other hand, a person can use this question to share a great deal of personal information. If the response you get lists several items or goes into detail about a particular interest or hobby, you’ll know you’re off to a great start. If the person asks you the same question, it’s a good sign!

“What’s the best thing that happened to you this year?” This question is good because it focuses on the positive side of life. Even if someone has been going through a really tough time, there’s bound to be something good that has happened in his or her life, as well. When you give someone the opportunity to share a happy memory, it brings joy to the conversation.

Similarly, “Is there anything special you’re looking forward to these days?” encourages the person with whom you are conversing to focus on the bright side of life. The answer might be something as simple as “I’m looking forward to my day off this week” or “I’m looking forward to sleeping in this weekend”. Then again, someone might have something BIG to share, such as “I’m looking forward visiting Europe” or “I’m looking forward to the launch date for my new business”.

You can learn a lot about a person by knowing what stories, movies or songs have had a significant impact on them or have influenced their lives in some way. Asking what a person’s favorite movie or book or song is can open the gates for an entire evening of conversation!

Finally, “Who is someone you greatly admire?” is a question that provides insight into someone’s personality. Depending on the answer and where the conversation leads, it might also give you a glimpse of what’s important in his or her life, what attributes he or she respects in another person and what he or she aspires to in life.

A good conversation flows easily

two men standing, three women sitting

It’s typically easy to tell if a conversation is going to go well after a few moments. It’s also possible, though, to have an awkward start, then find common ground and start to feel at ease. Especially if you’re nervous or shy around a particular person, don’t worry if it takes a little while to feel at ease with each other. Keeping the five questions mentioned in this post in mind can help you work your way through an awkward beginning. Before you know it, hours will have passed and you’ll still be shootin’ the breeze!

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