The Ultimate Funny Online Dating Questions

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How many times have you met someone online, liked their profile, proceeded to start a conversation, and got the shock of your life because of their cringy opener? We’ve all faced those eye-roll-inducing pickup lines and looked for the “unmatch” button. Now, if you’re looking for some ultimate funny online dating questions to start a conversation on dating apps, you needn’t look too far. We’ve got you covered.

Yes, the success of your online dating journey depends on the kind of questions you ask your dating app match. Since you are not meeting face-to-face, these online dating questions are your only shot at making a great, first impression. With a simple yet funny icebreaker question, you’ll be texting back and forth in no time.

Since we are looking to have fun and strike a connection, what better way to do that than by using humor as our aide. So, without further ado, here are the ultimate funny online dating questions you can ask.

15 Ultimate Funny Online Dating Questions

There’s no denying that online dating is gaining in popularity. Currently, there are about 66 million Tinder users in the world. In a report, 48% of dating app users say that they use these apps for fun, above anything else. However, that’s also to say a fair majority of these people end up in committed relationships if they strike a connection online.

If you’re wondering what are some funny deep questions to ask while texting someone online, you have to keep in mind that the key is to ask funny questions to get the ball rolling. You want to be different and out of the box, but you also want to carry on a conversation.

From personal experience on various dating apps, I can tell you that I always connected with people who had a great sense of humor and brought a good conversation to the table. So here are some funny random questions that you can ask your online date.

1. If you had to pick a superpower, which one would it be?

Who doesn’t wish they had a superpower as a kid? This is definitely a fun question to ask on a dating app. Especially if the person you’re talking to is a Marvel/DC fan, this can be the start of a very interesting conversation.

Who knows, you might even discover your mutual love for a particular comic book hero no one else knows about. Just like that, a fun online dating question has already got you two talking about things you love. Although, if you’re a guy, make sure you don’t answer with “X-ray vision”, it’s only going to get you ghosted. Congrats, you managed to get a superpower after all! You’re now invisible to your crush (ouch, sorry).

2. Ask some “would you rather” questions

“Would you rather” questions may not seem like the most interesting thing in the world, but these can actually turn into a gold mine of funny questions that will make your date laugh. They are funny random questions that will definitely lighten up the conversation, without really talking about anything in particular.

The fact that these simple yet intriguing questions continue to instigate conversation tells us that overthinking what you should send that Tinder match is something you should actually never be doing. The next time you’re putting off replying because you want your text to be supremely interesting, just send them any one of the following fun questions to ask on dating apps:

  • Would you rather have true love or a million dollars?
  • Would you rather have half of your head shaved off or one eyebrow?
  • Would you rather live without pizza or sex for a year?

The possibilities are endless, you can make these as funny or as flirty as you want. These are definitely the ultimate funny online dating questions you can ask, but try not to go overboard. After a while, you’re going to need to ask a few meaningful questions instead of just inquiring about whether they value sex more than pizza.

Related Reading: 101 Best Pickup Lines For Guys

3. If you were king/queen of X, what would your first decree be?

“If you were queen/king of this dating app, what would your first decree be?” This is sure to get a giggle out of your match. This question can be a funny online dating question, as well as one you can ask in person. The questions you thought would only work on dating apps work IRL as well and are great conversation starters on that awkward first date.

This can spark off the funniest conversation and you get to know a lot about the person you are talking to. If they reply with something humorous, you know you’re in for a good chat. All it takes is a bit of effortless humor to get things going.

4. So, what are your thoughts on pineapple on pizza?

funny online dating questions to ask him: Pineapple on pizza?
Do you consider pineapple on pizza blasphemy or bliss?

This controversial question can be a great conversation starter and will also tell you a lot about the other person’s life choices. Okay, maybe not everything about their life choices, but a lot about just how compatible you two are going to be.

Trust us, if they say they like pineapple on pizza, it might be time to unmatch (just kidding). You might love it too and have now found common ground. Funny dating app conversation starters can end up making you two figure out what you have in common and your combined hatred (or love) toward pineapple on pizza will give you two something to talk about.

5.  If you won a trip to go anywhere on Earth, where would you take me?

Now, this is one of the more uncommon questions you can ask. This can be funny as well as flirtatious and is sure to make them smile and contemplate. Right off the bat, you’ll show this person that you’re confident and amusing at the same time.

In fact, one of my friends struck gold with this question while using Bumble. She asked a guy what his dream destination with her would be and a year later, they were both backpacking across western Europe. So, you never know when you’re going to find the person who you would like to travel the world with someday. If you came here looking for funny online dating questions to ask him, you’ve got all you need.

6. What is the most ridiculous way you’ve hurt yourself?

This is a fun question you can ask on a dating app. You can even start this off by telling your date the stupidest way you’ve ever gotten hurt, and follow it up with a, “What about you?”

This will put them at ease and they will be more willing to share their amusing story with you.  Before you know it, you’re hearing about the time they fell on stage during a school assembly, embarrassing themselves in front of everyone. This is definitely a funny icebreaker question.

7. What would the title of your autobiography be?

I think mine would be called “A series of unfortunate events” and I’d be lying If I said I haven’t used this fun online dating question myself. Ask your date this question with a follow-up question about why they picked the answer they did. Not only will you get an anecdotal summary of their life, but you’ll also be able to quickly assess what this person might be like.

You can make this as goofy as you like, your answer will inspire your match to make their answer just as quirky. This question could very well be the epitome of funny online dating questions. Even though this will probably work on every dating app platform, since Tinder is notorious for not giving out too much information about someone beforehand, it could work especially well there. So, If you are thinking of funny questions to ask on Tinder, this is the only one you need.

8. If you had to spend 10 days wearing the same pair of clothes, what would you pick?

This humorous question will definitely make your date think hard. We all have favorite clothes but could we really spend ten days in them without changing? The answer they give will tell you a lot about their personality. Do they value comfort over style or are they just not ready to ever be caught wearing their joggers out in public?

If you’re trying to figure out whether you’ve got a fashionista or a PJ’s rocking girl on your hands, this funny online dating question to ask her will tell you all you need to know. P.S. if she says she’s going to be wearing Versace for 10 days, we’d suggest wearing your best clothes to the first date.

9. If you had the power to conjure up one thing and always be stocked up on it, what would it be?

This is one of the weird questions that will also tell you a lot about the other person. Whatever their answer is to this question, is the one thing they probably cannot live without at all. While we’re at it, ask yourself this question. What’s something you wish you always had in abundance? Makes you think, doesn’t it?

Your match is probably never going to expect to be hit up with this question, so ask away and watch him/her respond with excitement. This is not just a funny online dating question, it’s also a small insight into their life.

Related Reading: 100 Romantic Questions To Ask Your Girlfriend And Make Her Heart Melt

10. If you could only use only one Harry Potter spell, which one would you choose?

If the person you are talking to is a Harry Potter fan, this question will work like a charm! It can be a great conversation starter for you as well. 

Kathy, a friend of mine, and a die-hard Harry Potter fan told us that she loves the movies so much that she’s mentioned it on her Bumble bio. Obviously, she says she develops stronger connections with guys who talk about Harry Potter. 

11. Eliminate one: Game of Thrones or Star Wars

These two have got to be the most famous fantasy series of all time and chances are that your date has watched at least one of them.

Having to pick one is definitely not an easy task, but will tell you a lot about their preferences. This one isn’t really a deep funny question, but it does tell you what kind of a person they are. If they have not seen either, then ask them to suggest an alternative.

12. What is the most hilarious/crazy thing you’ve ever done?

fun questions to ask on dating apps: ask about drunk stories
Drunk stories never fail to lighten the mood

You can tell a crazy drunk story starring yourself before you ask your date. Brace yourself to hear a wild account of some drunken night they had while vacationing in Europe. This question scores a 10/10 if you’re looking for some entertainment.

If you’ve come across a teetotaler, however, it doesn’t necessarily mean they won’t have a good answer to this question. The idea is to break the ice as early as possible and get comfortable with sharing amusing stories with each other. This is definitely one of the fun questions to ask on dating apps.

13. What background track would you choose if you were about to get into a fight?

Heavy metal? Intense Hip Hop? Some Imagine Dragons maybe? Music sure says a lot about a person. Plus you also get to imagine a dramatic scene with your date walking ahead and bombs going off in the background.

Add even more dramatic music and voila, you have something out of an action movie. Make sure you create a fun scenario like this while talking to your date. Fun questions to ask on dating apps are all about how absurd the questions can be since a goofy question is what is going to elicit a goofy response.

So instead of asking the overplayed “What kind of music do you listen to?” give it a little twist and ask the question in a unique way.

14. If you had to live inside the mythical world of a game/TV show/movie, which one would you pick?

You get to know their preferences when it comes to games or TV shows and you also get to find out whether they pick a post-apocalyptic world or a world full of magic. This is a random funny question to ask your online date for an intriguing conversation.

Related reading: 7 Men Reveal The Cute Things Their Drunk Girlfriends Do

15. If there were a Zombie Apocalypse tomorrow, what would you do? 

This can work as a role-playing activity. You can discuss what happens if the world ends tomorrow with your date and create a scenario in which both of you are battling out zombies together. Can you suggest a better bonding exercise?

There are a million weird questions, uncommon questions, and funny random questions that you can ask online. That’s the beauty of online dating, the possibilities are endless. That is why 59% of the dating crowd thinks it’s a convenient place to meet people and, hopefully, build connections.

We hope that with this list of funny online dating conversation starters examples, your dating game is now going to be crazy good. However, as you dive into the conversation and strive to build connections, there are a few things you should keep in mind.

Points To Remember While Asking Funny Online Dating Questions

It’s great fun to ask the questions we gave you but when you are actually using these questions to know someone better there are some things you have to keep in mind:

1. Always be appropriate when asking online dating questions

You may be cracking jokes or hitting them with one of the aforementioned funny online dating questions, but you must remember to be appropriate at all times. You must always take note of the direction in which the conversation is heading.

There is a fine line between flirting and being inappropriate, and you don’t want to cross that unless you’re looking to get unmatched. I can’t even count on my fingers, the many instances in which my friends have told me how their new Tinder/Bumble/Hinge match started being totally inappropriate and they had to unmatch them. You don’t want to end up being that kind of guy to avoid on Tinder.

2. Let the conversation flow naturally

Personally, I hate forced robotic conversations. They can drag on which seems unbearable since you know there’s no real connection. So, don’t try to force these funny questions into the conversation. Let the conversation flow and use them to enrich the conversation when you feel the time is right.

3. Customise these funny online dating questions

Remember to not use all the questions verbatim or else you might sound too formal. If you want to make your date laugh, you must rephrase the question and weave it into the conversation in a suave manner.

4. Ask questions/make funny comments related to their bio

Apart from these questions, if you’re really looking to make an impression, it is vital that you ask questions related specifically to them. Their bio is a good place to start. Sometimes, instead of racking your brain for fun questions to ask on dating apps, all you have to do is take a look at their bio and ask them about that coffee place where they took their photo.

5. Build on what you already know

You know a thing or two about your online date thanks to the previous conversation, through their bio or social media profile. They might have told you that they like dogs and traveling etc. Build on these bits and pieces of information that you already have.

Related Reading: Online Dating Profile Examples To Attract Men

6. Keep things lighthearted

It’s best to keep online conversations lighthearted and not deep dive into serious topics too soon. This is when these funny online dating questions come in handy.

7. Don’t overshare

For the love of God, read the room and refrain from oversharing. No one likes to know too much too soon. It’s alright to share slowly and gradually, especially after you’ve been talking for a while. However, refrain from telling them about the scarring experiences of your life straight off the bat.

8. Keep your expectations low

Now, let’s be real, this person is probably talking to at least 5 other people on the same dating app. You cannot expect them to be fully dedicated to you, especially in the initial stages. Sure, after you decide to be exclusive the dynamic changes. But until then, don’t expect them to reply to all your messages instantly.

So, there you have it folks, the ultimate funny online dating questions coupled with the dos and don’ts of online dating for a smooth ride in the online dating universe. Online dating can seem easy but intimidating at the same time. The best thing for you to do, is to not try too hard. Instead, be your own charming self and you should be able to find what you’re looking for!

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