Interesting Conversation Starters

Your country is going to war. You bravely enlist. Soon after, you’re being shipped out to the frontlines, and your loved ones gather to say goodbye. Your best friend pulls you aside. You hug. This may be the last time you see each other. This might be your last conversation . . .

. . . and what do you say?

What’s up? How are you? How about this weather, huh? So . . . did you see the game last night? Welp, see ya later.

Not likely!

Great Conversations & The Seven Levels of Intimacy

Meaningful, deep conversations are the bedrock on which every great relationship has ever been built. You cannot have one without the other. Clichés—like the ones used in the absurd going-to-war example above—are like sand. Relationships built on clichés are doomed to crumble.

Our overreliance on clichés is a modern tragedy. We use them because they are safe, because they are comfortable, and because they avoid intimacy.

The thing is, the secret to incredible, inspiring, engaging, meaningful conversations is intimacy.

To illustrate just how important intimacy is for great conversation, I will be referencing Matthew Kelly’s The Seven Levels of Intimacy (assume all quotes below are from this work). In this book, Kelly discusses the layered nuances of intimacy—it is not just about sex, he notes, but instead it is the “mutual self-revelation” required for great conversations and deeper relationships.

The first level of intimacy, Clichés, which we’ve already hit upon, and the seventh level, Legitimate Needs, won’t be addressed here because—at both ends of the spectrum—neither make for great conversation starters (the former being too empty and the latter being too heavy).

The sweet spot for great conversation starters falls between levels two and six, depending on the situation. So let’s talk about it.

Facts: Did You Know?

The second level of intimacy is Facts. And while most facts are mundane, it doesn’t mean your conversation starters have to be.

“One of the redeeming qualities of facts is that they have the potential to stimulate us intellectually, to arouse our natural curiosity, and to teach us to fall in love with learning.”

While facts won’t help you really, really, really get to know someone, they can jumpstart an otherwise cliché-ridden and dull conversation (that can then eventually get you to the next levels of intimacy).

When to talk about Facts: If you must stick to facts, open with something surprising (even if a bit random). If you go beyond the weather, Facts can serve as great ice-breakers.

Interesting Conversation Starters:

  • Did you know . . .
    • . . . 10 percent of all the photos ever taken were taken in the last twelve months?
    • . . . there are more fake flamingos in the world than real ones?
    • . . . a duck’s quack doesn’t echo?
  • Tell me something about yourself that no one else knows . . .
  • What was the highlight of your week?

Opinions: The Danger Zone

Most relationships never make it past the third level of intimacy: Opinions. (gasp!)

Why are opinions so dangerous? Because they reveal ourselves more than clichés and facts. In order to have an opinion, you have to take a stance. And that stance might be different than someone else’s. Clichés and facts are passive and impersonal. Opinions are active and personal.

“Most relationships put one foot into the waters of opinions and then jump straight back into facts and clichés.”

Here’s the thing. A conversation will never be interesting until the first opinion makes its debut. If you want to get to know someone, eventually you’ll have to start drawing lines in the sand.

When to talk about Opinions: First dates (and during early courting), catching up with an acquaintance, or a casual conversation with a coworker. Be prepared to wade into the waters of controversy.

Interesting Conversation Starters:

  • What is the most beautiful song you have heard?
  • What does it take to be successful?
  • Do you believe in miracles?

Hopes and Dreams: Tell Me More . . .

Hopes and Dreams is the fourth level of intimacy. One of my dreams is to be a novelist. Unless specifically asked, I rarely share this with people—even friends. Why? Because it’s more than a fact. It’s a piece of who I am. A big piece. Instinctively, I hold onto these bits of me like they’re precious gold.

“Our dreams speak significantly about who we are, so they are a point of significant vulnerability.”

If you disagree with my opinions, I can live with that. If you laugh or scoff at my dreams, you are laughing and scoffing at me. That kind of rejection stings. But with high risk comes high reward . . . delving into Hopes and Dreams are some of the best conversation starters around.

When to talk about Hopes and Dreams: Hopes and Dreams are the best conversation starters. They are revealing, but usually not as controversial as opinions, and almost always lead to great conversations!

Interesting Conversation Starters:

  • What’s your dream job? What was it as a kid?
  • If you could go anywhere in the world, where would you go?
  • What’s one thing you always wished you could do well?

Feelings: Mining for Emotions

Yikes. As a man, I’m feeling this indescribable urge to skip this section. But for your sake, I will power through it. Feelings. The fifth level of intimacy. We all got ‘em, but—by my quick estimation—only roughly 50 percent of us actually like talking about them . . .

“Our feelings are the raw emotional nerve endings that very often reveal our brokenness, our humanity, our need to be held, listened to, and loved.”

Feelings can be tricky things to talk about. But with the right people, in the right places, at the right times . . . they can lead to incredible conversations.

When to talk about Feelings: Save Feelings for more established relationships—close friends, boyfriends or girlfriends, family members, or your spouse.

Interesting Conversation Starters:

  • Are you happy?
  • How do you feel most loved?
  • What makes you really angry?
  • When was the last time you felt pure joy? Why?

Faults, Fears, and Failures: Naked

Going through the levels of intimacy is kind of like stripping back layers of armor. Clichés are your iron breastplate, helmet, and shield. The sixth level of intimacy—Faults, Fears, and Failures—is the equivalent of being naked. The armor is off. You are exposed.

“When we are convinced that our significant other is dedicated to helping us become the-best-version-of-ourselves, we become willing to lay bare our faults and ask for help.”

Conversations this raw will be the most meaningful conversations you ever have—so make sure you are having them with the right people.

When to talk about Faults, Fears, and Failures: Reserve your brokenness for your primary relationships (like your spouse or parents), but if you’re feeling bold you can use some of these questions as conversation starters with friends and acquaintances.

Interesting Conversation Starters:

  • What is your biggest fear in life?
  • Tell me about your biggest regret or failure . . .
  • If you could change one thing about yourself, what would it be?

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There’s a reason freedom of speech is part of our first amendment. Conversations are the cornerstone of civilization. Without open, honest, and meaningful conversations, we’d have nothing. We’d be nothing. Can you imagine if America’s forefathers dealt in only clichés? Can you imagine if the great philosophers and leaders of world history dabbled in only the facts? Can you imagine if your grandparents never made it past a few controversial and opposing opinions?

Every great idea, every ancient and modern invention, every relationship on the planet was created by great, deeply intimate conversations.

Just think about that for a moment. No, don’t just think about. Find someone and talk about it. There’s no telling where your next great conversation will lead you.

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