Talking to new people — whether friends, family, or complete strangers — can sometimes feel awkward or intimidating. But starting a conversation doesn’t have to be stressful or boring! In honor of New Conversations Day on July 12, I’m sharing 5 quirky conversation starters that are fun, unexpected, and easy to try anytime, anywhere. They’re the kind that bring a smile as you begin — and somehow, that smile makes everything else easier.

Whether you’re at a summer gathering, visiting family, meeting someone new at the beach, or just out and about in the world, these lighthearted openers can help you break the ice and invite a real connection.

As for me, I’d say I’m an ambivert — someone who enjoys talking but also treasures quiet time. I’m not shy, and often strike up conversations with strangers — in grocery lines, parks, bookstores — and to the visible embarrassment of my kids, even elevators! I don’t do it to be the center of attention; I simply enjoy the little spark of connection that comes from a friendly word or a curious question.

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So if you’re like me — or even if you’re not — and want to invite a little more warmth, fun, and conversation into your everyday moments, here are a few playful ways to get started:

Let the Talking Begin: 5 Fun & Quirky Conversation Starters

1. Ask a Silly “What If?” Question

“If you could have any superpower for just one day, what would you pick?”
This kind of question taps into imagination and brings out someone’s playful side. It’s fun, unexpected, and opens the door to creativity and personality.
Why it works: It’s open-ended and lighthearted — no pressure, just a bit of fun. And best of all, it lets people share something delightful about themselves right away. I have seen it work well, many times over, in classes, meetings, and more. And we learn things about people we thought we knew as well as make friends of strangers.

2. Invent a Silly Award for Them

“I’m officially nominating you for ‘Best Smile of the Day’ — what’s your secret?”
It’s a compliment, but with a twist. Giving someone a pretend award instantly makes them smile (and maybe laugh) while breaking the ice in a gentle, playful way.
Why it works: Quirky compliments feel personal and thoughtful — and they’re disarming in the best way.

3. Comment on Something Weird You’ve Noticed Nearby

“Do you think that statue is secretly watching us?”
Sometimes the best conversation starter is just… noticing something. Pick something odd, funny, or out of place — and wonder out loud about it.
Why it works: Shared humor and curiosity help people connect quickly, and talking about something external takes the pressure off both of you.

4. Use an Unexpected Icebreaker

Quick! If your life had a theme song right now, what would it be?”
People light up when they talk about music — especially when it connects to how they’re feeling.
Why it works: This question invites storytelling, emotion, and creativity, but keeps things playful. The “quick!” adds just the right nudge of spontaneity.

5. Ask for a Totally Random Recommendation

“I need a new snack to try — what’s your absolute favorite guilty pleasure?”
This one always gets a smile. People love to share their little favorites — and you just might discover something delicious.
Why it works: Food is universal, and asking for a recommendation feels natural. The “guilty pleasure” twist adds a sense of fun and honesty.

A Few More Easy Ways to Spark a Conversation

If quirky questions aren’t quite your thing (yet), here are five gentler ways to get the ball rolling:

1. Lead with a Little Wonder

“What’s something that’s been making you smile lately?”
“If summer had a soundtrack for you this year, what song would be on it?”
Why it works: Open-ended and softly curious. A simple way to invite someone to share what’s on their mind or heart.

2. Compliment, Then Connect

Instead of a quick “nice hat,” try:
“That’s a great hat — any story behind it?”
Why it works: Compliments feel good. Asking for the story behind it makes the interaction feel more personal.

3. Use the Setting

Whether you’re at a BBQ, bookstore, or beach:
“Have you been here before?”
“What’s your favorite thing to do around here?”
Why it works: The environment offers natural openings — all you have to do is notice and ask.

4. Share a Slice of You

Start with something about yourself:
“I’m trying to read more this summer — any book recs?”
“I’m on a new recipe kick — got a go-to summer dish?”
Why it works: When you open up first, it makes others feel safe to do the same

5. Don’t Fear the Pause

Not every second has to be filled. Let the moment breathe.
Why it works: Silence isn’t awkward when you’re comfortable. It gives space for thought and helps the conversation flow naturally. And while I am kind of like Rosina in this quote below from Cutting for Stone, I have learned over the years that silence speaks as well, and have learned to relish it.

“Rosina took silence as a personal offense, and spoke into empty rooms and chattered into cupboards. Genet, almost six years of age, was showing signs of taking after her mother, telling herself stories about herself in a singsong voice, creating her own mythology.” – Cutting for Stone, Abraham Verghese

So, Conversation Starters…

Conversations don’t have to be complicated. Sometimes, all it takes is a playful question, a curious thought, or a simple compliment to open the door to something real. Whether you’re connecting with someone new or rekindling an old friendship, these starters can help.

So this New Conversations Day, and every other day as well, let’s be a little braver, a little more curious, and a little more playful with our words. Who knows? That random snack tip, silly “what if,” or compliment on someone’s shoes might just lead to laughter, connection — maybe even a new friend.

Bookish Five: Books That’re Great Conversation Starters & More

Of course, one of my favorite ways to spark a conversation — or deepen one — is through books. Stories connect us, give us something to talk about, and sometimes even teach us how to be a better friend, listener, or curious question-asker. So today, I bring you books around that – conversation sparkers/friendships and so on.

A book I finally got back to (after starting it earlier this year) is Six Days in Bombay.

(1 & 2) Book Beginnings and First Line Friday

BOOK BEGINNINGS ON FRIDAY is hosted by Rose City Reader. What book are you happy about reading this week? Please share the opening sentence (or so) on BOOK BEGINNINGS ON FRIDAY! Add the link to your blog or social media post and visit other blogs to see what others are reading.

Happy Friday and welcome to the FIRST LINE FRIDAY, hosted by Reading is My Superpower! It’s time to grab the book nearest to you and leave a comment with the first line.

3 Friday 56

THE FRIDAY 56 is hosted by Anne at HeadFullofBooks. To play, open a book and turn to page 56 (or 56% on your e-reader). Find a sentence or two and post them, along with the book title and author. Then link up and visit others in the linky. 

4 Book Blogger Hop

The purpose of THE BOOK BLOGGER HOP is to give bloggers a chance to follow other blogs, learn about new books, and befriend other bloggers. THE BOOK BLOGGER HOP is hosted by Ramblings of a Coffee Addicted Writer.  

How many weekly bookish posts do you put on your blog and/or social media? 

While I need to go back to posting more review posts (somehow lost that along the way), of late, I have been trying to join in weekly bookish memes – Top Ten Tuesday, Friday memes like the ones in this post, Six Degrees of Separation (monthly), and also include books for almost every other post in some way or the other. So I guess, almost a 100% of the posts I have on my week, whether one or more, is bookish in some way.

🗣️ 5 Quirky Titles That Spark Conversations

Picture books & middle grade reads whose titles themselves are sure to be great conversation starters!

1. We Don’t Eat Our Classmates by Ryan T. Higgins
   What happens when a dinosaur tries to make friends… by nibbling on them? This is a delightful, hilarious, and a tad outrageous story that is sure to get everyone giggling. Great way to open up chats about empathy, self-control, and being the new kid.
2. The Strange Case of Origami Yoda by Tom Angleberger
   I love Yoda, and I attempt origami (for I love it), so of course, how could I love this book (series, actually)!!! Is Dwight’s paper Yoda actually giving good advice? This fun and weird middle-grade mystery blends Star Wars with middle school drama. It is sure to get readers talking about social dynamics, believing in yourself, and whether origami can be wise.
3. The Day the Crayons Quit by Drew Daywalt
   I am sure you have heard of this one already, many times over. When I first saw this book, my first thought was, oh no!, and second one was, Why?!!! I love this story of how fed-up crayons write letters to their owner about unfair treatment — from overuse to neglect! A clever, colorful story that will spark both laughs and conversations about creativity, emotions, and seeing things from another point of view.
4. My Mouth Is a Volcano by Julia Cook
   I absolutely loved this title, and the many other books from Julia Cook on similar topics. Great for SEL sessions in the classroom or at home. In this one, when Louis can’t stop interrupting, he says it’s because his words erupt! A playful, relatable take on blurting out and learning patience — perfect for talking about listening skills and self-regulation.
5. The Book with No Pictures by B.J. Novak
   No pictures? All words? This book still makes everyone laugh — especially because the reader has to say silly things out loud. It’s an instant crowd-pleaser that turns reading time into a performance and sparks endless fun. For all that I adore about picture books, I am also about (well, you know that already) WORDS!! And this is a book I had to check out when I first saw it, and one that has remained a cool one to look at (read) every so often since.

And Now, the End of This Post

Dear reader, which of these books featured/listed here have you read/will you pick to read first? Any other suggestions for books about friendships and/or conversation starters?