How do you get both of these things done? You use a great ice-breaker question. But you need a big repertoire of icebreaker questions, so you can choose the best one for the person you have just matched with. Why can’t you use the same one? Because if you have read through their profile and already know a bit about them, you want to tailor those dating icebreaker questions to what you already know. For example, if you know that your date binges on mystery novels, you wouldn’t be asking them about characters from sci-fi books or movies. Or if they are an agnostic or an atheist, you wouldn’t be asking for the type of music they believed would be played in Heaven and Hell. But if you don’t have enough information, you may just have to go in the cold.
Never fear. There are loads of good icebreaker questions to choose from that would work for anyone in general and be great conversation starters.
Taking a Look at First Date Icebreaker Questions
First things first. You want to choose an icebreaker question that not only starts a conversation and elicits interesting answers. You want one that seems a “fit” for the personality of the date but also tells something about you, even if in a veiled way. If, for example, you really like to sing at karaoke bars, then you might ask, “What would be your ‘go-to’ karaoke song?” You get the idea.
So now, let’s take a look at some great dating icebreaker questions that will both engage your date and give you some insights into their personality.
What’s the Best Vacation You Have Ever Had?
First, you will get some insights into what your date likes to do for leisure time and the types of travel they do. If, for example, they love Las Vegas, or their best trip was mountain climbing in the Carpathian Mountains of Eastern Europe, then you know a lot. If you are a bright light kind of travel person, perfect. If mountain climbing will never be your thing, then you know to move on to someone else. And online dating makes that easy to do. Back out diplomatically and don’t hurt their feelings.
What Conspiracy Theories Do You Believe to be True?
Your politics may be really important to you. And you will never date someone who does not share your political beliefs and values. This is a quick way to find out if your politics are aligned. If they are, then you will feel comfortable moving forward with a second date and beyond.
On the other hand, if you are not a political animal, there are plenty of other conspiracy theories – aliens among us, for example. Don’t ask specifically about political ones – let your date take the reins here.
Are You at Your Best in the Morning or at Night?
If you know anything about these two types of people, you will get lots of insight into your date. A night owl tends to be more creative, a risk-taker, an adventure-seeker, and can be impulsive. An early bird is more down-to-earth, organized, and highly focused on their work and achievement. Sometimes, opposites attract and complement each other, making a partnership that is very successful. On the other hand, a person may want a partner that is just like them. That’s an individual choice.
What is the Craziest Thing You’ve Ever Done?
Now you get the chance to see how adventurous or full of fun your date is. If you want someone who is kinda “crazy,” this will let you know. If your date has a tough time coming up with something crazy, or the craziest thing is some silly dorm prank that was really not “out there,” then your next conversation may need to be a soft goodbye.
On the other hand, you might be looking for someone more conservative to balance out your “crazy” tendencies and a more “down-to-earth” person will get bonus points in your eyes.
What Is One Food That You Will Never Eat Again in Your Lifetime?
This is just a fun topic to begin a conversation. You won’t get much insight from the answer, but follow-up questions can include you sharing your hated food, and then moving on to other things you love and hate – some latest fashion, for example. You can even make a bit of a game of it. “Name an animal you love and one you hate.” “Name a movie you love and one you hate.” As you play this game, you will gain more insight into personality, and it’s just fun banter.
How Do You Spend Your Free Time?
This is one of the best conversation starters of all because it will reveal so much about the person you are dating. What a person chooses to do in their spare time will let you know pretty quickly whether your date is someone you want to spend more time with. If your spare time consists of gaming, the gym, and hitting a few bars, you may not favor someone who visits art galleries and reads.
What is Your Spirit Animal?
Now here’s one of those funny icebreaker questions that will get someone thinking, if they haven’t chosen a spirit animal before. There can be awkward silences before answers are given. They may be serious (“I’m a lion because they are strong and fierce”), or they may be creative and fun (“I’m a hummingbird because my life is so hectic, and I have to eat 3X my weight just to keep my metabolism on high” or “I’m an anteater cuz sometimes I stick my nose where it doesn’t belong”). This question is a fun way to start a conversation about our strengths and faults.
If You Could Make Something Illegal that is Not, What Would It Be?
This is another fun way to spark further conversation. Maybe the answer is something like taking more than 5 minutes to place an order at the drive-through. Maybe it is strolling down the center of a shopping aisle so that people in a hurry can’t get by. These kinds of funny icebreaker questions can set you on a long conversation about your biggest pet peeves and the fines that should be given to irritating and annoying people.
What is the Most Embarrassing or Worst Thing You and Your Best Friend Have Done?
This is one of the best conversation starters because your date will be able to tell you about their good friend and recall an event that they now look back on in either horror or laughter. And the details of that embarrassing moment will tell you lots about their personality. You can then share the most embarrassing thing you did, and both have a good laugh.
What is a Fashion Trend You Would Outlaw?
We all have styles we think are ridiculous or that look ridiculous on certain people. How about men or women in bikini swimsuits with bulging stomachs hanging out? How about 8-in high heels that could be used as weapons? How about wearing pajamas in public shopping places? It might be ear gauging, mullets, puffed-out lips that look like fish, grills, hammer pants, etc. This can easily start a conversation that can turn into something hilarious, leaving both of you laughing. You can also go back to your high school years and dis on fashion trends that you now see as absolutely hideous.
Do You Have a Celebrity Crush?
Okay. So this one isn’t all that unique and creative among ice breakers. But it can lead to more conversation starters. If there is a celebrity crush, then there are reasons for that – what are they? And do you have one or more and why? This can lead to movies you each like and more. Remember the whole point of these ice breakers is to get to know someone but also to start longer conversations to reveal more about one another.
When was the Last Time You Really Got Angry? And Over What?
We all have triggers for anger, but real anger should probably be over important things, not trivial matters. It’s one thing to have anger over being betrayed or sorely mistreated. It is quite another to have road rage over being cut off on the road or someone forgetting your birthday. The larger issues can be start points for more conversation and sharing.
What is Something You Buy Too Much Of?
This can be a hilarious conversation starter. We all have obsessions we can’t resist. It might be shoes, books, hats, plants, fitness equipment, paintings, candles, and such. When you share these things and laugh about them, you share a funny flaw you have in common.
If You Had to Give a Speech Right Now, What Would Be the Topic?
Now here’s a good conversation starter and the chance to find out something important. If your date can immediately give you a topic for an impromptu speech, that topic is something of deep interest to them – they obviously know a lot about it. What about you? How would you answer the same question?
What’s the Weirdest Habit You Have?
This is just a fun question that may get you just as funny an answer. People do have weird habits – having conversations with themselves when they are thinking about something, eating the least food on a plate first, turning off the microwave 1 second before it finishes so as not to hear the beep, talking to their pets like they were people. You’ll come up with your own too, and reciting them to each other can be a pretty happy conversation.
If You Were Ever Arrested, What Crime Would You Have Committed?
Now here’s an ice breaker that could go in many directions, and be sure to have your own answer ready too. Most people will not answer with crimes of violence (if they do, maybe back out of this match), but there are some “crimes” that are meaningful and not as serious – protesting, painting on publicly-owned walls or sidewalks, etc.
What’s the Best Advice You’ve Ever Been Given?
While this won’t show a lot about someone’s personality, it will show a bit about their values. There’s a huge difference between advice that honors and respects others and advice that promotes selfishness and narcissism. Listen carefully to what that advice is, and you will gain some insight.
What’s the Weirdest Food Combination You Like?
Again, this is just a simple fun question to ask when online dating. It will probably lead to a conversation on a lot of weird food combinations – you’ve had these before with others. Still, while not the best conversation starter, it can add a bit of humor.
Describe Yourself With Three Adjectives
Before you ask this question, make sure that you have three adjectives in mind to describe yourself, because you know where this is headed. In fact, you might want to have 3 adjectives that are more serious and three that are a bit more creative and humorous. If you get a response that is serious (e.g., kind, respectful, organized, etc.), and you want to continue the conversation, then use your serious list. If you get quirky, funny adjectives, then use your other list.
What’s the Silliest Thing You Own?
This question can get people talking about their “things,” but those things can reveal more. For example, one reported answer was a bottle opener that had the head of Pinocchio with a long nose. That answer led to talk of where they had each traveled, because the bottle opener was bought in Italy while the person was on vacation in Europe.
If You Could Invent Something, What Would It Be?
This one could take some thought, but you might see how creative your date can be. Usually, that question is answered in terms of what would make life easier and more comfortable or efficient. There are common and sort of boring answers, like bathtubs that would automatically clean themselves cereal bags with zip tops, etc. But you might find a creative soul who wants slippers with LED lights to avoid stepping on girls bumping into things when they get up in the middle of the night.
Summer or Winter?
This can be just the first of several pairs you fire off and ask your date to answer very quickly. Come up with a list in advance – mountains or beaches, pools or lakes, orange or apple, coffee or tea, vanilla or chocolate, red or white wine, and so forth. Then ask your first date to fire some back at you. You will learn a bit about each other in a fast-paced and fun way.
If a Magic Genie Gave You Three Wishes, What Would They Be?
Here’s a first-date question that will give you lots of information and insight right from the start. For one thing, it will let you know if you are dating someone who is generally more serious or more playful. Serious stuff will be things like world peace or a cure for cancer (and there’s nothing wrong with such answers – they show concern for humanity). On the other hand, it’s fun to see what a more playful date might answer – snow and ice that melts in front of me as I walk, everything being sold for a price that does not include pennies, toilet paper that never runs out, etc.
If You Could Re-incarnate, What Would You Come Back As?
This is a great online dating starter question. Why? Because once an answer is given, that answer will lead to lots more conversation about why that choice was made. An answer might be pretty serious, but it also could be pretty funny. What if your date wants to come back as a tree or a giraffe?
How Many Things Are on Your Bucket List, and What Are the Top Three?
The Bucket List Family (@thebucketlistfamily) • Instagram photos and videos
Ernest Hemingway once said, “Every man’s life ends the same way. It is only the details of how he lived and how he died that distinguish one man from another.”
Everyone has things they want to do before they die. And this question about a bucket list is probably one of the more serious you will ask. The answers can be telling too. Where might they want to travel? What experiences would they like to have? Do they want to go skydiving or build a small cabin on an isolated island? You’ll learn things about their personalities.
If You Could Dance to Any Song, What Would it Be?
This is one of those ice breaker questions that show you as just a regular nice person. It’s not too intimate off the bat and the answer does not require deep thought or creativity. The other plus here is that you will learn something about their musical taste. Once the favorite song is revealed, you can begin a conversation about that genre of music, your favorite artists, etc.
What Do You Wish Would Be Free Forever?
Online dating should include icebreaker questions that are both serious and light, or that at least give your date the option to be serious or funny. This is one of those good online dating icebreaker questions that does just that. A person might respond with answers such as health care or education, answers that can lead to lots of follow-up questions. Or they might reply with something sillier like coffee or in between like flowers.
What is Something You Believed as a Kid that was Just Ridiculous?
Here’s a quirky question that will have lots of fun answers. For example, a person might say they believed that thunder was angels in heaven dropping potatoes. Or, as one person answered once, that umbrellas would act like parachutes which proved to be false when the close friend who told them that also convinced them to try it off the garage roof. Dating questions like these are the stuff of which hilarious conversations are made.
What’s the Most Distracting Thing for You Online?
Everyone has a guilty pleasure that will take them from their work at hand or eat up lots of their free time. It might be their favorite social media platform, YouTube videos of cats, etc. this is one of those first date good ice breaker questions for dating because it’s not too personal and can lead to lots more conversation. Online dating should not start out with intimate questions.
Dating Apps are Where It’s At Today
Online dating apps are not going away anytime soon. In fact, they are exploding as people look for matches before getting serious about in-person meetups. Getting to know someone means coming up with ice breaker questions for dating that will let both people explore each other in a safe and fun way. If you are struggling to find ice breaker questions for dating, this list should give you plenty of options, no matter what types of dating apps you are using. Get going and have fun.
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