One of the most enjoyable aspects of dating is getting to know someone new. But, as you progress beyond the formal, “Where are you from?” or “What do you do for a living?”, you can ask some fun and engaging questions that make your date even more memorable.
These questions aren’t just getting the information you need, they spark laughter, deep conversations, uncovering shared interests, and discovering the unique parts that make someone who they are.
So, are you looking to know what are some fun questions to ask when dating? You’ll want to check out our guide for some great pointers and the right fun questions to turn ordinary dates into cherishable memories.
Why Should We Ask Fun Questions On Dates?
The answer to this question is a no-brainer, really. But in an effort to make you realize why they’re so important, we’ll endeavor. When you ask fun questions, you break the ice between you and your partner.
Dates in the beginning can be awkward, where both of you are unsure of what to say or how to act and engage in long periods of awkward silences.
But when you ask fun questions on dates, they’re conversation starters that help ease those initial nerves. They also help display both of your senses of humor, which is a surefire way to tug at the heartstrings.
Fun questions can lead to unexpected deep conversations, which can reveal a lot about someone’s personal beliefs, values, and personality than a generic question like, “What are your hobbies?” would.
Whether you ask an online dating coach or your serial dater buddy, they’ll all tell you that fun questions are the way to go!
You’re not only sharing interest in the other person as you ask them these fun and thoughtful questions, but you’re also setting the tone for future dates and building a solid base for a deep connection.
Some Categories of Fun Questions
We can already sense that you’re curious about what kind of fun questions to ask on dates. Check out some categories of these questions we’ve compiled below so you can pick and choose the ones you feel most attuned to. Or ask them all gradually as your dates progress.
1. The Ice Breakers
Icebreakers are perfect for starting dates when you’re just getting to know each other. These are light and easy questions and get the conversation flowing without too much pressure on either person.
For example, you could ask, “What’s your favorite way to unwind on a weekend?” or “If you could have any superpower, what would it be?” These questions are not too prying and invasive, letting natural and organic exchanges take place.
Icebreakers lead the way for the rest of the date, and makes it easier and not awkward to transition into more in-depth topics.
2. Quirky and Creative Qs
Once the conversation is rolling, throw in some quirky and creative questions to keep things interesting and interactive. These can be playful questions and may lead to unexpected answers, which are great as insights into a person’s imagination and sense of humor.
“What brings out your creativity the most?” or “What’s the weirdest food you’ve ever tried?” are some questions which are great for showcasing your fun and playfully weird side. You’re also learning about each others’ unique tastes and experiences along the way.
3. Hypothetical What Ifs
Hypothetical questions are really fun because they let you in on someone’s creativity and explore different aspects of their personality.
They invite the other to imagine themselves in different situations, which can be entertaining and insightful and often lead to hilarious and memorable responses.
For instance, you can ask, “If you won the lottery tomorrow, what’s the first thing you would do?” or “Would you rather travel to the past or the future?” Both of these questions are completely hypothetical and pave the way for some really thoughtful, creative, and unique responses.
These can also lead to discussions about values, priorities, and long-term goals, which are important topics for any budding relationship. There’s nothing more rewarding than peeking into someone’s fun and unapologetically authentic self, and hypothetical questions let you in on that.
4. The Ones With Relationships and Values
As your dates progress, you’ll want to delve into topics that help you understand the other person’s relationship expectations and values. Don’t get us wrong—these questions are still fun, but they also give insight into how compatible you are in the long run.
Ask, “What’s your idea of a perfect date?” or “What quality in a partner gives you the ick?” These questions will help you gauge how aligned your values and goals might be and also deets on where you both draw the line, setting the example for a great relationship.
Tips For Asking Fun Questions On Dates
While we’ve given you various categories and examples of fun questions you can ask on dates, it’s only fair if we equip you with some tips so you can ask them the right way. We’re at your service!
Be Genuine and Curious
When you’re asking fun questions, make sure to be genuine. Ask questions because you’re truly interested in hearing the other person’s response, not just to fill the awkward silence between you two. Genuine curiosity is attractive and leads to more meaningful exchanges. Inauthentic curiosity is easily picked up and might shoot potential down before anything happens.
Follow-Up With Your Own
Listening to the other person’s fun responses to your fun questions is great, but make sure to follow up with your answers after they’ve finished responding. Conversations are two-way streets, and it’s important to keep the exchange balanced while also giving the other insight into your interests.
Adapt. Readapt.
While fun questions are exciting, never forget to read the room. If the other person seems uncomfortable, the setting isn’t quite right, or they seem a little thrown off by your question, it’s okay to hold off on certain questions. You could just say, “Let’s save that for the next date,” and effortlessly let them off the hook.
Adjust your approach and response based on how the conversation is going and how comfortable both you and your date are feeling.
Mix It Up
Variety is the spice of life, they say, so don’t stick to just one type of question. Throw in light-hearted, quirky, and deeper questions to keep the conversation dynamic and interactive. The best conversations are those where topics and subjects are all over the place, without leaving a trace of how you got there.
Mixing and changing things up keeps things interesting and lets both of you explore different avenues and facets of your unique personalities.
A Few Red Flags To Be Aware Of
Now, let’s give you some pointers to avoid when it comes to asking fun questions on a date. Because let’s face it, sometimes we can all cross the line without knowing we’ve gone over it.
- Don’t Force It: Understand that not every date is going to be filled with laughter and endless conversation, and that’s perfectly okay. Don’t force someone to answer questions they don’t seem eager about. If a question doesn’t land, move on to another topic gracefully.
- Too Personal! We know how tempting personal topics can be, but it’s smart to avoid overly personal questions on the initial dates. You can’t spring up asking about someone’s childhood traumas or political beliefs on the second or third date. It’s off-putting and idiotic.
So, stick to lighter topics until you have stronger rapport and back and forth.
- Non-Verbal Cues: It’s very important to pay close attention to the other person’s body language and tone of voice. If they seem uncomfortable or disinterested, it might be time to switch up.
When you’re attuned to non-verbal cues, you make sure that the date remains enjoyable for both parties. And being aware of these subtle elements can be a huge turn-on for your date and vice versa.
