Struggling to Meet New People? Use 11 of Our Favorite Thought-Provoking Questions to Spark Instant Connection

We’ve all found ourselves in the situation of meeting someone new, whether it be at a party or even on a first date. You’re trying to get to know the person across from you and engage them in a meaningful conversation. You also don’t want to talk about yourself too much and give the impression that you’re not a good listener. 

Then it happens: The awkward lull in the conversation…

You struggle to come up with something to get things back on track, but you’ve already asked what they do for a living. Maybe you ask about the local sports team, only to find out they don’t follow sports. Then it goes from bad to worse: How about this weather we’re having? You cringe as soon as it leaves your mouth!

Your mind screams out at you: What have I done? 

You see the light dim in the eyes of the person you’ve been talking to as they mutter about how crazy the weather has been. They shuffle their feet in that way that tells you they’re looking for an escape strategy while you look down at your drink sheepishly. Before you know it, they’re excusing themself to get a refill, and you’re left to contemplate why you couldn’t ask anything else.

Well, the good news is, we’re here to help you take your conversation skills up a notch.

How Do You Have Engaging Conversations?

Everyone wants to be a brilliant conversationalist, but it definitely comes easier for some. Whether it be general shyness or even social anxiety, meeting new people can be a nerve-wracking experience. A lot of that anxiety comes from the fear of not having anything to say and losing the interest of the person you’re talking to.

Conversations are like social job interviews: You want to present yourself in a way that makes the person you’re talking to want to have you around. Much like selling yourself to a prospective employer in an interview, you feel like you have to show why you’re awesome when you’re meeting new people, too.

But there’s a secret that turns this expectation on its head: It’s not about you! 

Meaningful conversations are built on a good back-and-forth that provides both participants with opportunities to ask, listen, and talk. We fall into the trap of trying to do too much in meeting new people. We don’t actively listen because we’re worried about what we will say next. Most of all, we dread that awkward moment when it feels like we’ve run out of things to talk about, so we’re trying to think of the next thing to say to avoid that moment at all costs.

Having an arsenal of thought-provoking questions in your mind can keep the conversation flowing. But it’s important to remember that everyone has a story to share, so don’t ask questions just to ask them. Actively listen to the answers your conversation partner is giving you.

Just one question can open and carry a conversation if it’s a good one. Luckily, we have eleven of these questions that you can use to keep any conversation going.

#1: What’s Your Story?

Everyone has a story to share, and they want to share it with you. Asking this question will probably shock the person you’re talking to, but once they start answering it, you’ll see how great it is to spur conversation.

Asking a person what their story is gives them the opportunity to open themselves up as much as they want. They can tell you absolutely anything about themselves: hopes, fears, dreams, successes, challenges, and more. The conversation can literally go anywhere from this one simple question.

#2: What’s a Fun Thing You Did as a Kid?

Most everyone has fond memories of growing up. It was a magical time when the entire world was in front of you and the possibilities were endless. There were no expectations, and the responsibilities of the world were nowhere around.

Asking about something fun your conversation partner did as a child can bring a smile to their face as they remember the good times of their youth. It also helps the discussion move toward learning more about each other, as childhood memories can lead directly into talking about your life so far.

#3: When’s the Last Time You Failed at Something Spectacularly?

Now, this might seem like the type of question you might not want to ask someone you’re trying to get to know, but it’s all about how you ask it. You’re not asking the person to share their biggest failure. You’re asking them about comically failing at something. 

Each of us has that story that feels like an episode of I Love Lucy where everything we tried just failed epically. This question can lighten the mood and get both of you smiling and laughing at the absurdity of the situation. If everyone has a story, then everyone could certainly use a good laugh!

#4: What’s Your Favorite Book/Movie/Show/Music?

We put these under the same question because they’re all variations of the same basic thing. Asking someone about their favorite media is great because it lets them talk about something they’re passionate about. No one feels indifferent to their favorite of anything.

Not only does this type of question get a passionate response, but it can also give you new things to experience. If their favorite book, etc., is something you’ve never checked out, you may have missed out on something great.

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#5: If You Could Go Anywhere in the World, Where Would It Be?

Asking someone where they would like to travel is a great way to build a meaningful conversation. Talking about destinations can open up discussions about different locales and give you both ideas of places you might have never thought about traveling to.

Thinking about vacation spots also helps people ease into a conversation. It helps put you in the mindset of being relaxed and excited to experience something new. It can also help deepen your connection if you find you both have similar tastes in destinations. Who knows, maybe it can lead to having a travel buddy.

#6: What Are Some Things You’re Willing to Spend a Little More On?

The answer to this question can tell you quite a bit about the person you’re talking to. Even if it’s something as simple as a good cup of coffee, it tells you what the person values and sees as worth it.

Their answer can also give you an idea for potential get-togethers in the future. Whether it be a date or a simple hang-out session, knowing what a person’s indulgences are gives you an opportunity to show that you paid attention to what they told you and considered them enough to treat them to one of their guilty pleasures.

#7: What’s Something You Used to Believe in That You Don’t Anymore, and What Changed?

This is a deeper-level question that can give you a lot of insight into your conversation partner. It allows you to get an idea of what they value now and what led them to those beliefs. It can also tell you a lot about how open they are to change.

Talking about a change in something that was a fundamental belief also helps build trust between people. This isn’t a topic a person might always feel comfortable discussing, but if they do, it’s a good sign they feel a connection with you. 

#8: What’s the Biggest Challenge That You’ve Overcome? 

Everyone wants to feel successful and accomplished. Asking someone about a challenge they were able to overcome helps them feel good about it all over again. It also tells you about what obstacles they’ve successfully faced in their life.

This question can also allow you to show how supportive you are. Perhaps you can give them your perspective on how you would’ve tried to overcome the same challenge. It’s a wonderful chance to show your empathy and deepen your connection.

#9: What Matters Most to You?

This gives you insight into what drives the person you’re talking to. Do they cherish family or friends? Maybe they’re driven by achieving more from their career. They might want to experience more of the world by traveling.

Discovering what a person holds most important tells you so much about them. It also leads the conversation to what both of your hopes and aspirations are and what you’re doing to achieve them. Discussing what you’re passionate about always deepens a conversation and connection.

#10: What Do You Value Most In a Friendship?

Asking someone what they value most in a friendship gives you an inside look into whether you and the person you’re talking to are compatible. It not only tells you what they look for in a friend, but it also leads you to assess if you have the qualities most important to them.

The biggest challenge in asking this question comes in their answer, though. When looking to connect with someone, you can be tempted to try and conform to their answer. Remember that while you’re trying to make a friend, you want to remain true to yourself. Don’t be tempted to misrepresent who you are just to appeal to someone else’s ideals!

#11: What Do You Want Your Legacy to Be?

Another thought-provoking question to ask someone is what they want to be remembered for. This is similar to asking: What do you think someone would say about you in your eulogy? While that question can come across as a bit dark, asking what they want their legacy to be is more upbeat.

Everyone wants to feel as though they’ve left an impact on the world, even if it’s just on their family and friends. Asking this question can make them think about their accomplishments or what they’ve done to enrich the lives of the people around them. It also gives them a chance to assess if there’s more they want to do or achieve.

Deep Questions Lead to Deep Connections

Approaching someone with thought-provoking questions can lead to incredible conversations. As we’ve said, everyone has their story, and they want to share it. Asking some of the questions we’ve posed here can help you break the ice when meeting new people and give you better options than the standard small talk.

You’ll never find yourself awkwardly asking about the weather ever again. Now you can confidently engage new people in conversations that help your connections embody Greatness!