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How to Have More Entertaining Conversations

How to Have More Entertaining Conversations

What if I told you that some of the best conversation exchanges are about things that never occurred and never will?

Say hello to the hypothetical statement – or hypotheticals as I affectionately refer to them. Probably the most entertaining type of statement in the conversation universe. A single hypothetical can launch a conversation into a world of fictional fun.

I was sitting in a coffee shop writing and someone came over and asked if the comfy chair next to me was available. I didn’t feel like talking because I was engrossed in my writing, but after I told him it was free, he sat down, got comfortable, and said, “If I start snoring loudly, just kick me.”

We both laughed. I responded, “I’ve got some ice left in my cup I could pour on you if that would work better.” He laughed again, and I went about my work. Either of us could have continued a conversation very naturally from there if we wanted, all about an imaginary event — falling asleep and snoring in a chair! There was nothing glamorous about the event either – but simply discussing the hypothetical possibility, within the context of a coffee shop – was very funny.

Hypothetical statements don’t require the imagination of an artist or the wit of a playwright. Many are quite simple and quick. Check out the following example:

“I’m going for a run, although I’ll probably faint in this heat.”

You could have just told your wife, “I’m going for a run,” but that wouldn’t be entertaining, would it? Adding some hypothetical scenario takes it to a whole new level. You could have added any number of hypotheticals about possibly being bitten by the neighbor’s vicious dog, chased by cops, etc.

Look at the World Without Hypothetical Statements

To quickly illustrate the power and range of hypotheticals, let’s look at some real examples WITHOUT and WITH a hypothetical component.

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Obviously, you weren’t privy to the actual conversation, but my hope is you can imagine how B-O-R-I-N-G some of these statements are without hypotheticals and how they completely transform the instant the hypothetical is added:

Without Hypothetical: Yeah, I was going to call you this morning to see if you were coming in.

With Hypothetical:Yeah, I was going to call you this morning to see if you were coming in. I wanted to make sure you weren’t stuck in a ditch or something.

Without Hypothetical:

JACK: I’m so glad they finally built the café down here.

JILL: Yeah, before this I was eating fast food every day.

With Hypothetical:

JACK: I’m so glad they finally built the café down here.

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JILL: Yeah, before this I was eating fast food every day. I must have gained like twenty pounds!

Without Hypothetical: I have to go give that presentation now.

With Hypothetical:I have to go give that presentation now. Anyone want to come see me embarrass myself?

The Hypothetical and the Exception

Hypotheticals often come in the form of an exception. Check out this example:

Your friend mentions the topic of making beer.

YOU: I’ve always wanted to have a home brewery in my basement. That would so cool! Except I’d probably end up throwing most of it out!

FRIEND: Maybe you should have a bakery instead. I think you would like making sweets even more than beer. Except you would probably end up eating everything before you had a chance to sell it!

What Might be a Possible Explanation?

The hypothetical can take the form of a playful explanation for why some event or behavior occurred.

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For example, you are leaving a neighborhood party when someone comments about your five-year-old.

FRIEND: Your son has been so good this whole time.

YOU: Thanks. It worked out well.

The conversation could end there. Or you could add a playful reason as to why your son behaved so well.

YOU: Thanks! We got lucky. Someone probably snuck him a few beers from the fridge.

Check out another example:

Your friends are talking about hair loss.

YOU: Yeah, it sucks, I’m sure I’ll be bald in about two years.

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FRIEND: Really, you look like you still have all your hair.

YOU: Yeah, well, not really.

Or you could also provide a hypothetical reason.

YOU: That’s because I’m wearing a toupee – a really good one. I glued it down.

The Almost Realm

Many great hypothetical statements exist in the realm of the “Almost” did/said/happened. This is often more interesting than the literal truth. It’s a very important technique in telling stories as well.

For a simple, but effective example, imagine someone asking: “How’d the event go?”

You reply “It was fun…the tent almost collapsed…but overall, it was a good time.” Or “It was fun…nothing burned down, so that was good.”

This gives the other person something else to connect to. “Well, I’m glad nothing burned down! That wouldn’t be good.”

Hypotheticals require a little imagination and a playfulness, which isn’t easy to replicate when you’re by yourself.  Regardless, it’s a habit that doesn’t come easily unless you make some effort. See if you can finish the following statements with a hypothetical statement:

  1. My team is playing tonight, if they ______, I’ll ________.
  2. I can’t stand mushrooms…if _________.
  3. Your beard is getting really long, you could ________.

A lot of times, just forcing yourself to add a “if…  it could…. it should… it would have… it might… I’ll probably… ” can help trigger some imaginative, entertaining statements!

More by this author

Gregory Peart

Gregory is the author of The Conversation Code: How to Upgrade Your Social Skills and Your Life. He regularly teaches adult social skills classes.

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Last Updated on July 3, 2020

30 Small Habits To Lead A More Peaceful Life

30 Small Habits To Lead A More Peaceful Life

In today’s world, true peace must come from within us and our own actions. Here are 30 small things you can do on a regular basis to increase your overall sense of harmony, peace, and well-being:

1. Don’t go to every fight you’re invited to

Particularly when you’re around those who thrive on chaos, be willing to decline the invitation to join in on the drama.

2. Focus on your breath

Throughout the day, stop to take a few deep breaths. Keep stress at bay with techniques such as “square breathing.” Breathe in for four counts, hold for four counts, then out for four counts, and hold again for four counts. Repeat this cycle four times.

3. Get organized and purge old items

A cluttered space often creates a cluttered spirit. Take the time to get rid of anything you haven’t used in a year and invest in organizational systems that help you sustain a level of neatness.

4. Stop yourself from being judgmental

Whenever you are tempted to have an opinion about someone else’s life, check your intentions. Judging others creates and promotes negative energy.

5. Say ‘thank you’ early and often

Start and end each day with an attitude of gratitude. Look for opportunities in your daily routine and interactions to express appreciation.

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6. Smile more

Even if you have to “fake it until you make it,” there are many scientific benefits of smiling and laughing. Also, pay attention to your facial expression when you are doing neutral activities such as driving and walking. Turn that frown upside down!

7. Don’t worry about the future

As difficult as this sounds, there is a direct connection between staying in the present and living a more peaceful life. You cannot control the future. As the old proverb goes, “Worry is like a rocking chair. It gives you something to do, but it won’t get you anywhere.” Practice gently bringing your thoughts back to the present.

8. Eat real food

The closer the food is to the state from which it came from the earth, the better you will feel in eating it. Choose foods that grew from a plant over food that was made in a plant.

9. Choose being happy over being right

Too often, we sacrifice inner peace in order to make a point. It’s rarely worth it.

10. Keep technology out of the bedroom

Many studies, such as one conducted by Brigham and Women’s Hospital, have connected blue light of electronic devices before bed to adverse sleep and overall health. To make matters worse, many people report that they cannot resist checking email and social media when their cell phone is in reach of their bed, regardless of the time.

11. Make use of filtering features on social media

You may not want to “unfriend” someone completely, however you can choose whether you want to follow their posts and/or the sources of information that they share.

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12. Get comfortable with silence

When you picture someone who is the ultimate state of peace, typically they aren’t talking.

13. Listen to understand, not to respond

So often in conversations, we use our ears to give us cues about when it is our turn to say what we want to say. Practice active listening, ask questions, process, then speak.

14. Put your troubles in a bubble

Whenever you start to feel anxious, visualize the situation being wrapped in a bubble and then picture that sphere floating away.

15. Speak more slowly

Often a lack of peace manifests itself in fast or clipped speech. Take a breath, slow down, and let your thoughtful consideration drive your words.

16. Don’t procrastinate

Nothing adds stress to our lives like waiting until the last minute.

17. Buy a coloring book

Mandala coloring books for adults are becoming more popular because of their connection to creating inner peace.

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18. Prioritize yourself

You are the only person who you are guaranteed to live with 24 hours a day for the rest of your life.

19. Forgive others

Holding a grudge is hurting you exponentially more than anyone else. Let it go.

20. Check your expectations

Presumption often leads to drama. Remember the old saying, “Expectations are premeditated resentments.”

21. Engage in active play

Let your inner child come out and have some fun. Jump, dance, play, and pretend!

22. Stop criticizing yourself

The world is a hard enough place with more than enough critics. Your life is not served well by being one of them.

23. Focus your energy and attention on what you want

Thoughts, words, and actions all create energy. Energy attracts like energy. Put out what you want to get back.

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24. Assign yourself “complaint free” days.

Make a conscious decision not to complain about anything for a whole day. It might be harder than you think and the awareness will stick with you.

25. Surround yourself with people you truly enjoy being in the company of

Personalities tend to be contagious, and not everyone’s is worth catching. Be judicious in your choices.

26. Manage your money

Financial concerns rank top on the list of what causes people stress. Take the time each month to do a budget, calculate what you actually spend and sanity check that against the money you have coming in.

27. Stop trying to control everything

Not only is your inner control freak sabotaging your sense of peace, it is also likely getting in the way of external relationships as well.

28. Practice affirmations

Repeat positive phrases that depict the life and qualities you want to attract. It may not come naturally to you, but it works.

29. Get up before sunrise

Personally witnessing the dawn brings a unique sense of awe and appreciation for life.

30. Be yourself

Nothing creates more inner discord than trying to be something other than who we really are. Authenticity breeds happiness.

Featured photo credit: man watching sunrise via stokpic.com

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