When I hear icebreakers, it conjures up flashbacks to awkward youth group moments with hula hoops and relay races or running around. Unfortunately, the weird feeling associated with “getting to know you” stuff hasn’t faded with adulthood. If anything, it’s gotten even worse.
The best thing about a first date is that you have infinite places to start a conversation. But the worst thing about a first date is that you have infinite places to start a conversation! How do you choose, what’s too personal, what’s interesting, what requires follow-up—there’s just a lot to navigate.
Have no fear, your non-awkward icebreakers are here! This list of ten simple but solid questions will you start the conversation without getting too personal or too short on that first date.
A little conversational refresher
Before we head into the list, let’s pause for a quick reminder about what makes for a good conversation. It’s simple: Back and forth. A volley can’t happen if you’re asking yes or no questions, so try to ask open ended questions that could lead anywhere.
You can also use answers to build more questions . But be careful to remember that your first date (or second date!) isn’t an interrogation. Sometimes it’s easy to get stuck in the loop reminiscent of a therapy session or job interview. You find that instead of having a natural conversation, you’re answering everything the other person says with another follow-up question. If you’re in the loop, find something common in what they’ve shared and reply with a statement about the same topic, but with your life as the focal point.
10 comfortable icebreakers
What’s your favorite holiday?
There’s nothing wrong with going totally classic with your icebreakers, especially if conversation is just not flowing. Any favorite of any kind—food, music, travel destination, season of the year—is a tried and true icebreaker.
How do you like to celebrate your birthday?
What better way to make someone comfortable than reminding them of some of their happiest times on a day all about them? Plus, this is one of those icebreakers that has the bonus questions of how they celebrate now, or what their ideal celebration would be if money was no object.
What movie character have you always felt was secretly based on your life?
Sometimes it’s hard for people to talk about themselves. But with this question, you can crack open the shell by finding a fictional character they project themselves onto. It’s pretty safe to say that most of us identify with a movie character, and it can show a lot about how we see ourselves or wish we did.
If you were on a televised talent show, what would your talent be, and would it surprise anyone?
As far as light-hearted questions, this is one of those icebreakers that’s great. You’ll learn something unique and also flatter your date. A win-win if there ever was one!
What is the thing you could watch or read again and again?
I read once that The Office is the comfort food of television. That resonated with me because I’m an avid fan of the show. But I also loved the idea that we gravitate towards the same movie, TV show or book during times in our lives when we need to feel safe. Your answer to this icebreaker can probably say a lot about you.
When you were a kid, what did you want to be when you grew up? How did that pan out?
While childhood could be a sticky situation to discuss, this question is a safe way to share in the camaraderie. Because no matter how we grew up, the one thing we have in common is that we all were kids at one point, dreaming about becoming “grown ups.”
What weird thing did you believe when you were a kid and found out later wasn’t true?
Again, at one point we were all kids and we all believed something silly. For me, I thought my dad invented Dairy Queen’s Dilly Bars. But there are more universal childhood truths—like that leaving the light on in the car while your parents were driving was illegal. This is a great place to find common ground and share some laughter.
What superpower would you want? Or what superpower do you think is a total waste of a superpower?
This is just a fun question to get the conversation moving. It will show off your creative side and could even spark an interesting debate in the realm of fantasy.
What was the first concert you ever went to?
Usually, this comes with a story of how a person ended up at that concert, why they loved or hated it, and how their music taste has changed or not changed since that time. For example, my first concert was technically a children’s musician when I was a toddler. So my tastes have definitely changed. There is our segue to a new topic: music!
What’s the story you always tell at parties?
This is one of my favorite questions, because most people have a go-to story that they love to share with people. One that’s really hilarious or uplifting or surprising. It can be a good way to get to know something personal (but not too personal), and it can also usually get the conversation flowing because a story will break up the back and forth if you get caught in the dreaded interview volley.
Building blocks or puzzle pieces
It’s important to remember that dating modestly means revealing yourself slowly, bit by bit. That means essentially, it’s all going to be icebreakers for a while, or it may feel that way. As tempting as it may be to sit down with a list and spend all night talking getting to know one another, don’t rob yourself of the opportunity to draw the process out over time.
When you take the time to get to know someone, you’re using building blocks and watching what the structure becomes, little by little. If you jump into a line of questioning or interrogation, you’ll get all the same answers but it will be more like a puzzle you have pieces to that don’t seem to fit, which can be frustrating for everyone.
Even though they’re icebreakers, it’s really just the tip of the iceberg. There’s a lot more under the surface that God will spend your entire relationship revealing to you. Be patient, and don’t be nervous!
