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How to Have More Entertaining Conversations

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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.”

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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.

How to Have More Entertaining Conversations
How to Have More Entertaining Conversations
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