You're talking to a CEO at a business event.
You're charming the woman of your dreams.
All of a sudden… you go silent. You don't know what to say – it gets awkward.
You blew your chance.
How do you start a conversation? More importantly, how do you keep one going?
That's what we're covering, gentlemen. I'm showing you 15 easy conversation starter questions you can use any time.
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Starter #1. Who Do You Text The Most?
This gives you insight into the person you're dealing with. It's especially useful to learn about a potential date. Let's say she texts her mom often – it means that she's close to her family. Texting co-workers? She's career-oriented. If she texts her ex… that's baggage that you don't need.
Starter #2. What Is Your Dream Job?
I like this question because it's aspirational. It prompts the other person to think outside the box and consider their wildest dreams. This conversation starter question could make them consider ideas that they haven't in months… maybe years.
Starter #3. What Is Your Morning Routine?
Maybe the person has a rigid system in place when they wake up. They rise at 5 AM every morning, hit the gym, and are ready to work by 7.
Perhaps chaos rules them – they don't have a set time, they sleep in and take the day as it comes. You get a sense that they may not be the most organized.
Do they drop the “I've been meaning to do it” excuse? Then you know they procrastinate.
Starter #4. What Would You Do With A Million Dollars?
Let's face it – a million dollars isn't a lot of money. You can't take it and live happily ever after.
It is a SIGNIFICANT amount of money, though. It can start a business, pay off debts, invest in the stock market… even buy a house. How the person would use that money will help you understand how they'd manage finances.
Starter #5. Do You Believe In Love At First Sight?
This is a more personal question better-suited for somebody that already has a rapport with you.
I do believe in love at first sight. When I saw my wife for the first time, I knew she'd be the one. Other people are more skeptical – it hints ar a more cautious approach to relationships.
Starter #6. Do You Believe In Soul Mates
A soul mate is somebody ideally suited for another – compatible in every way. This is similar to question 5 but far deeper. Again, this is appropriate for somebody with a more established relationship. Don't open a conversation up with this!
Starter #7. Do You Believe In Luck?
This is an easy conversation starter question that opens the doors to more conversation. A person's view of luck is influenced by their life experiences.
Someone who suffered a slew of bad experiences could believe themselves to be cursed. On the other hand, a man who narrowly escaped a terrible accident might think they're blessed.
This may lead them to open up about those experiences!
Starter #8. Tell Me About Yourself
Ok, not technically a question – but it's too easy to pass up. It's a totally open-ended request. The other person can tell you anything, and this is valuable. Whatever they lead with is what is most important to them – whether it be a job, hobby, or current challenges.
Starter #9. What's Your Story?
Everyone thinks they have a great story. They have unique experiences that left them unique insights – and they're dying to tell you. This question invites them to indulge in themselves a bit by telling you some tales. `
The more you let somebody speak about themselves, the more they'll like you for it. All you have to do is listen carefully.
Starter #10. What Did You Do Last Weekend?
A very safe and shallow question is to ask how their weekend went. You can learn more about what they do in their free time. It's an opportunity to learn about the hobbies they pursue outside of work.
Starter #11. Do You Believe In Aliens?
Ok, I admit this is a curveball, but hear me out. This conversation starter question throws ANYBODY off. I like to use it in job interviews for that reason. It also hearkens back to childhood memories, when all of us had that sense of wonder and discovery.
You might even find out something interesting about the person. Perhaps they hold a strong belief in aliens after all!
Starter #12. How Is Your Week Going?
Another simple, easy question. They might tell you about having an amazing work week – packed with promotions, raises, and new experiences. On the other hand, this may open the flood gates to something deep. The person might be struggling with professional and personal challenges – this may push them to vent.
Starter #13. What's One Thing You Miss From Childhood?
This goes back to question 11 – that age of curiosity and discovery in everyone's childhood. They are bound to have memories they want to start over. It could be a friend they had that they lost touch with or grandparents that aren't around anymore.
You never know! Personally? I'd give anything to go back!
Starter #14. What's Your Favorite Restaurant Around Here?
This is a simple way to get a taste (get it?) of the other person's culinary inclinations. You can easily deduce whether they love a hearty steak or prefer Japanese cuisine. Our diet impacts us severely, so this is an essential piece of information!
Starter #15. Who Is Your Role Model?
People emulate their role models – making this an important question. If a man admires Harvey Specter from Suits, you might assume he strives to be as suave and well-dressed as the famous TV lawyer.
It's not always about celebrities, though. They can just as easily want to emulate a mom or a dad, meaning they put family high on the pedestal – that's good!
Conversation Starter Questions
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