Hands down one of the easiest ways to keep a conversation going is to ask questions. It’s simple because you’re taking a lot of the work out of that exchange. When you have interesting and funny questions to ask a girl ready to go they can be used as excellent conversation starters that can feel effortless.
It’s important that you don’t just rapid-fire questions at your date. Instead, just weave them into your conversation if things start to slow down. In case you’re stuck for great funny questions to ask, we’ve got you.
I’m about to give you 405 great questions for you to fall back on. To make sure you’re covered no matter the situation, I’ve even broken it up into 14 different types of questions — don’t say we don’t look out for you!
If you’re in a hurry, check out the topics below and jump straight to the section that fits your current situation. Different environments call for different questions but most importantly, go with whatever fits your personality.
Like many things in the dating world, your delivery is far more important than the words you use. Before we get into the list of funny questions, let’s talk about how to implement these questions in the first place.
Playing 21 Questions can be interesting in some scenarios. But for the most part, you want to avoid asking a bunch of questions back to back.
If your exchanges start to slide into a question-and-answer vibe, it can feel very dry and forced.
Rather than asking these questions to evade an awkward silence, use them to kick start a fresh topic.
As an example, when you ask her a funny “would you rather” question, her answer can lead you on a long, interesting tangent. Particularly if you’re familiar with the idea of conversation threading and can pick a part of her answer to run with.
Imagine she answers your question by saying “Option A. Because I grew up in New Orleans and my family would always do xyz. . .”
It’s so easy to keep a conversation going based on her answer alone. You can talk about New Orleans, a similar thing your family would do or even why you’d choose Option B.
Already, this hypothetical question and answer has given you three tangents to run with. Once you get a little practice with conversation threading, that one question can launch an entire evening’s worth of conversation.
This is important to make sure your delivery comes across as fun and interesting rather than feeling like an interview. I like to keep my dating conversations light and fun regardless. It lets me be cheeky on occasion and get away with a lot more than if I was very serious all the time.
Remember, these are funny questions to ask a girl. They’re meant to be fun and exciting!
If you can keep these tips in mind, you’re going to get the most out of these questions and the two of you will have a great time. Remember, the best way to look dorky with these questions is to make it serious and dull.
You’re better than. I know it and she’s about to see for herself too.
One of the best compliments you can receive on a date is that you’re “funny”. Humor is such a powerful thing and can be a great way to break down those initial walls. When you can keep your date laughing, you’re both sure to have a great time, even if things don’t go as planned.
If it starts to get a little dry on your date, these questions might be all it takes to turn that around. Intentionally silly and light-hearted, they can spark a totally new and fun conversation. And it is a great way to get to know someone.
A simple question to answer with a definite dad-joke ending. Good for a cheap laugh and a serious question at the same time.
This is serious business, obviously. You can’t just go eating a PB & J all willy nilly.
Nobody enjoys the awkwardness of sitting there while everyone sings. This question might be a tough one.
A little more risque, it can be a non-threatening way to bring sex into the conversation as well as an interesting answer.
Pickup lines are classically cringeworthy. Time to see what her sense of humor looks like.
If you’ve already been on a date, feel free to switch this one up a little. Either way, you just never know when those zombies are coming for us.
If you think about it from the outside, humans have some pretty weird rituals, huh? Walking the same route every day for no reason? Hmm.
Obviously she’s taking you — you’re great! The question is, do you both share the same taste in travel destinations?
This question usually brings about an interesting storytime. Ridiculous injuries rarely have a boring story attached.
Chocolate? The bank account? Supplies at the local homeless shelter? Which direction will she go here?
This question leaves the door open for her to get a little risque too. Will she talk about some silly text message she sent a friend or her collection of nudes? That’ll depend on her personality and how comfortable she is with you.
With so many distinct voices to choose from, it’s always interesting to see the answers to this question.
Again, you just never know when this will become important. Is she the one you want by your side when it all kicks off?
This is a great way to see what she thinks of herself. Sometimes it’ll give you an insight into her best friend and the shenanigans they get up to as well.
Similar to the question above, now you’re about to see if you fit the mold for her usual taste in men. No matter the answer, this is a fun topic.
We all have that one thing we like to do to unwind, right? Terrible reality show? An unusual hobby? You’re about to find out!
This is just a goofy question but it’s sure to bring about some creative answers. We’ve all done some speed-vacuuming when we heard mom was nearly home, right?
The perfect segway into suggesting the next step in your date.
Another question that calls for a silly, creative response. Have some fun with this one!
We all have at least one answer for this, right? We thought it would be so different.
Another question that we all have a guilty answer for. Admit it, you fell into some hilarious trends growing up too!
Such a great prompt for a hilarious story. Just make sure you have your own answer ready for this one as well.
Are you about to relate on your hatred for hand-washing dishes? Who knows, maybe it’ll be something far more obscure. Only one way to find out.
I love this question because it asks for a small amount of vulnerability but it’s also fun and lighthearted. It’s also sure to deliver an amusing response.
This question is a great way to demonstrate confidence. You’re comfortable with the fact other guys approach her. She probably has a fun story attached as well.
We take so much of what we do for granted. The question is, what part of a man is she most curious about?
Does she enjoy the smell of fresh laundry or is a mild case of OCD about to be exposed?
Just about everyone loves ice cream. Now it’s time for you both to get creative with those flavors. Maybe a future date idea to see if you can create it at home?
For women in particular, this tends to be an easy question. Knowing her favorite scent can be helpful down the track too.
Too many David Attenborough documentaries perhaps? I say bring on the random facts.
As someone who never progressed their card game prowess further than “Snap,” I can always relate to these answers.
High school relationships were an interesting time, weren’t they? Bring on the cringey responses.
Chihuahuas? It’s chihuahuas, isn’t it? Maybe cats.
Make sure you follow up with a “why” on this one. There’s sure to be a fun backstory or trend behind it.
Party tricks and hidden talents are always a good time. Especially if she can demonstrate it on the spot.
This is just a good, clean and funny question. We’re all guilty of it so nobody is safe.
Why is it that we buy the most random things when we travel overseas?
Now it’s time to bring out her mischievous side. It’s a silly yet interesting concept and always gets a laugh.
Objects or herself, the story is sure to be a fun one. Sit back and enjoy the hilarity!
As someone who uses dating apps often, I love hearing about these. People do some weird things in dating but hey, at least it lowers the bar for the rest of us.
Online dating in particular seems to bring about the best stories. Maybe it’s the relative anonymity? Who knows.
For me, it was the mailman. Getting paid to drive around and pet people’s dogs? Sign me up!
You might learn a little about her personality type with this question. Fiercely independent? Cute and cuddly? Mostly though, it’s just an easy, funny question to ask.
For most of us, the early years of dating brought about some interesting decisions. It also meant some cringe-inducing mistakes — why not look back on them together and laugh about it?
This is another simple yet fun question. Not something we all think about each day, so enjoy figuring it out together.
We all have our pet peeves, huh? Why not exchange hilariously irrational hates? Who knows, maybe you both share the same ones.
Even if she says a habit that you’re prone to, this is a fun conversation. Like with most of these, there’s probably an amusing example that goes with it.
Pranks make for great stories and they’re rarely boring to either tell or listen to.
There are so many great options to choose from here. Maybe you’ll get some ideas as to where you two should go next?
Funny dating stories are always hilarious. This is also another way to demonstrate that you’re not the jealous, insecure type. Talk openly about her dating history, it’s not like it changes anything!
When you’re chatting with someone you like, getting to know them can be fun and exciting. One of the best ways to do that? Ask questions!
More specifically, funny questions help to keep this process interesting for both of you. The conversation that comes from each of these questions is going to tell you so much about her. There are also a lot of flirty questions to ask a girl that you should consider using as well if you want to take things to a more intimate level.
Perhaps more importantly, it’ll help her get to know you too. As with any conversation, there will be some back and forth and, inevitably, you’ll end up giving your answer for these questions too.
This is a great question because she’ll often follow it up with why that person is her crush. It can be an excellent look at what she values in a person. Remember though, this isn’t to be taken too seriously.
Getting kicked in the groin? The potential to go bald? So many things for us to fear.
Everyone has at least some kind of guilty go-to for those quiet nights, right?
It’s unlikely this question has come up before so the two of you can figure out the best one together.
What can I say? We’re a strange species. We seem to do things for no apparent reason. . .
A backflip? Running man? The latest TikTok?
With so many skills we could acquire, we all have some kind of answer for this one.
I find this question to be an interesting one. Some talents can be so helpful to everyday life.
Department store? Outdoor equipment? You just might learn more from this question than you expect!
Whether you find some common ground here or have a playful argument, it’s still a fun question!
61. What’s your weirdest deal breaker in online dating?
62. What do you wish was more common in the dating world?
63. What was your wildest Halloween costume?
64. Sandwiches or wraps, which is the master race?
65. What’s the most ridiculous thing you’ve ever done for minimal reward?
66. If you could go back to a time before anyone had smartphones, would you want to?
67. What’s a talent you have that no one knows about?
68. If you could choose one annoying but minor curse to place on anyone you choose, what would it be?
69. Did you ever have an imaginary friend growing up?
70. What’s the worst excuse you’ve ever used to call in sick from something?
71. If you could be any Disney character, who would you want to be?
72. Have you ever been irrationally scared of something?
73. If we could all read each other's minds, where would be the most awkward place to go?
74. If the world was ending tomorrow, what three things would you want to do before midnight?
75. What kid’s movie still scares you as an adult?
76. What movie or TV show did you like as a kid but realize as an adult that it’s kind of messed up?
77. If you designed a movie poster for your life, what would the caption say?
78. What’s the best dare you’ve ever seen completed in a game of Truth or Dare?
79. What flavor do you wish could be made into ice cream?
80. What phase are you most thankful to have grown out of?
Just like the above section, asking a girl interesting questions is an excellent way of getting to know her.
It gives you an insight into their life, their priorities and thought process without it feeling like an interview. Goofy questions keep your conversation fun and engaging but are just as effective at getting to know the other person.
The better you can be about casually weaving these into a conversation, the easier it’ll be. Over time, it’ll just happen naturally.
If you find the conversation is getting too serious, these questions also serve as an easy way of changing the topic.
Jumping straight in with the real talk — definitely not a first date question but a good one for getting to know her down the track.
Is she part of the ear-wiggling master race?
The environment is important to us all — how far have you gone to save it?
A polarizing topic, some people get very wrapped up in these opinions. Others couldn’t care less.
Some people are addicted to their phones, others take days to reply. Is she living for the ‘gram?
A silly question that’s sure to bring about some amusing conversation.
We don’t get a second chance to make new old friends. Sometimes old friendships can be a great sign of how she treats those she cares about.
No walking under a ladder while holding a black cat, okay?
Time to find out if she’s the adventurous type or prefers to play it safe. Which do you prefer?
Again with the real talk. Some school tests were tough, okay?
91. Where do you stand on dogs sleeping in the bed?
92. Who do you think would win a staring contest out of the two of us?
93. What three words would you use to describe yourself?
94. Can you do any interesting tricks with your tongue?
95. Can you hum while you plug your nose?
96. How do you go assembling IKEA furniture? Are you a pro or should you be left alone for that one?
97. Can you say the alphabet backwards or are you bound to fail every sobriety test, even when sober?
98. How well do you handle compliments?
99. How well do you handle constructive criticism?
100. What wild conspiracy theory seems most plausible to you?
101. Do you prefer to spend time in the kitchen or do you prefer to eat out?
102. What’s the scariest experience you’ve ever been through?
103. What’s the most useless purchase you’ve ever made?
104. What was your favorite childhood toy?
105. Do you consider yourself a romantic?
106. What’s the most romantic thing you’ve ever done for someone?
107. Are you the person that shows up 10 minutes early or 20 minutes late?
108. What’s the most ambitious life goal you’ve set for yourself?
109. You just won a million dollars — what’s the first thing you buy?
110. Do you prefer clean-shaven? A full beard or somewhere in between?
When you’re in a relationship, it can be easy for things to fall into a routine. You begin to take your time together for granted and feel as though you’ve learned all you need to about the other person.
Even if that’s true, asking your girlfriend funny questions can be entertaining. Both sitting on the couch engrossed in Instagram and Snapchat? Why not mix it up with a funny question out of left field?
Since the two of you are already so comfortable with each other, this can completely change the tone for the night. Who knows where these tangents will take you. No matter what, it’ll be more fun than sitting there staring at your phone.
If you’re the dad joke type, you might have found your new biggest fan. Or a source of so many future groans.
There are two types of people in this world. What kind of monster bites their ice cream, right?
Stress is something that affects us all. Has she cracked the code?
This can be a difficult situation to navigate. Be ready with the follow-up questions to see how she dealt with it.
Some people just aren’t cut out for the kitchen.
Either option has to be better than 2020!
A jolly old man who gives presents or an obscure hermit?
Maybe she’ll give you a live performance some time.
The Tooth Fairy is a what?!
An even funnier question if you’re already bald.
121. Do you think I’m a goofball?
122. Do you think psychic abilities exist?
123. What’s the biggest decision you’ve ever relied on luck to decide?
124. Do you think you’re a good judge of character?
125. What’s the most obvious sign that I’m turned on?
126. Have you ever blamed someone else for something you did?
127. Have you ever fired a gun?
128. Have you ever tried (or succeeded) to learn a new language?
129. What’s the biggest kitchen nightmare you’ve ever found yourself in?
130. Have you ever performed in a talent show?
131. Did you ever skip school to go do something fun?
132. Have you ever used a pickup line or someone? How did it go?
133. Have you ever had to take a bathroom break in the woods?
134. Have you ever taken self-defense classes?
135. Do you love it when a Disney movie breaks out in song?
As we’ve mentioned above, funny questions can be an excellent way of getting to know each other. While most of them are easy, light questions designed for a bit of a laugh, they don’t have to be.
When the timing is right, you can also use some funny questions to get a little more personal. To learn things about her that you may not have found out otherwise.
These funny personal questions might not be the most suitable for a first date but maybe a second or third. They’re about pushing past the superficial but to do that, you need to have a level of comfort first.
Settle in for a wild ride if the answer is yes!
I’m pretty sure we all have at some point, it’s just the degree that varies.
Oof, time for a little reflection on this one.
The responses to this question are always hilarious. Uh-oh.
Do you believe in psychic powers or is it all an elaborate ruse?
Story time! There’s no such thing as a dull story about getting caught naked.
A very personal question, this one will bring up some deep conversation if she’s comfortable talking about it.
There’s at least someone we all wish we could have back, even just for a day, huh?
Every now and then you just have to mix things up. Sometimes you’ll even discover something you love.
Smoking? Drugs? Something more obscure?
146. Have you ever had a crazy ex? What’s the most “out there” thing they did?
147. Do you have any recurring dreams or nightmares?
148. Do you often remember your dreams?
149. Have you ever written a love letter?
150. Have you ever kept a love letter you’ve received?
151. How did you meet your best friend?
152. What’s one action you really appreciate from a partner?
153. How do you feel when people sing Happy Birthday to you in public?
154. Do you feel as though you handle stress and pressure well?
155. What’s a less common physical attribute you find attractive in a partner?
156. Are you the type to give second chances to a friend or just move on?
157. Have you ever stopped to help a random stranger?
158. Do you have (or have you thought about getting) any tattoos?
159. If you could have one magical power and nobody could know about it, what would it be?
160. If you were a billionaire, how do you think you’d spend your time?
161. Have you ever kissed a friend of the same sex?
162. Have you ever slept with a friend? Did you regret it?
163. Have you ever lived in another country or could you see yourself doing that?
164. If you were into a guy at the bar, what would you do about it?
165. What personal development are you most proud of?
Taking the time to learn who she is on a deeper level is so important to dating. Particularly if you’re looking for a relationship but even for hookups.
This might sound counterintuitive but I assure you it helps. It’s about building trust and comfort, which is far easier when you’re going beyond the basics.
By taking the time to ask these types of questions you’re showing that you’re more than just a one-trick pony. You’re capable of having a meaningful conversation and actually care about who she is.
If you’ve spent time chatting to friends about their Tinder experiences, you’ll know how refreshing asking deep questions can be.
Been there, done that. Do not recommend.
This is a very deep question but you just might get a bit of insight into her earlier life.
Physical attributes? Skills? Knowledge?
We all ought to be in the pursuit of happiness. Are you at your happiest point right now?
Do you think being the other gender would bring advantages to your life?
This one might stir some playful conflict!
I’d have to say the ability for captivating storytelling. Command the room with the simplest of stories.
Some of us have seen enough and it’s time to leave. Looking at you, Florida.
Hammock field tester? Maybe you’re in charge of playing with puppies every day. The possibilities are endless!
We’d probably all like to live forever. Does it count when it’s in robot form, though?
176. If you could trade places with someone for a day, purely for their benefit, who would you trade with?
177. Do you think people should be capped at a maximum net worth?
178. What’s a personal trait you wish you could change about yourself?
179. What part of your personal development do you struggle with the most?
180. What song or memory improves your mood almost instantly?
181. When you’re 80, what do you think you’ll be most proud of from your life so far?
182. When you’re 80, what decision do you think will bring the most regret?
183. What’s one thing you tried and refuse to ever do again?
184. Do you think most people are inherently good or bad?
185. What family memory makes you smile the most?
186. What’s your favorite thing to do when you need some “me” time?
187. What brings you the biggest sense of fulfillment?
188. When was the last time you truly took yourself out of your comfort zone?
189. As a child, did you ever run away from home?
190. Are you a structured planner or the spontaneous type?
191. At a party, do you want to be the life of the party or does that actually sound like a nightmare?
192. Do you think your life is better or worse now than it was 5 years ago?
193. Has religion ever been a big part of your life? Is it now?
194. What’s your favorite way to get exercise?
195. Do you know what your #1 love language is?
Silly yet thought-provoking questions can be another way to keep your interactions exciting. They’re simple enough that these questions don’t feel like work, yet they’re still intriguing.
They also maintain a level of humor that keeps the date fun. Like most of the funny questions on this list, they’ll also help you to understand how she thinks too. How does she approach these thought-provoking topics?
For some of you, these questions might even be the best fit for your personality type. I know that for myself, fun questions like these don’t feel out of place.
Yeah, I have no idea either. It seems like a strange choice.
How well do you really understand evolution?
Was there ever such a thing as a round boxing ring?
Just a little food for thought. Seems like a convenient coincidence, huh?
Some things we just take for granted.
No Googling allowed on this one.
Just like the UFO sightings. Was it aliens all along?
At least they wouldn’t have to travel far for a drink. I wonder if they get sick of water though.
The actual answer is kind of complicated and not too well known. Spoiler: Satan is actually just a Hebew word meaning “accuser” or “adversary”. The more you know.
206. Why do you think people are still willing to pay so much for diamonds?
207. If people from Poland are called Poles, why aren’t people from Holland called Holes?
208. You have to replace the handshake with a new gesture — what do you change it to?
209. If you passed out and somehow woke up in the year 2200, what would be your first question?
210. If you could jump forward 1,000 years, what would you miss the most from right now?
211. Why is it that we drive on a parkway and park on a driveway?
212. Who do you compare yourself to the most?
213. What important lesson did life teach you the hard way?
214. What do you wish you focussed more on 5 years ago?
215. If you had 10 minutes to speak to your 18-year-old self, what would you say?
216. What’s one book you think everyone should have to read in school?
217. What’s an important life skill you wish they taught in school but didn’t?
218. On your low days, where do you find inspiration to get things done?
219. Do you think tears are a sign of strength or weakness? What about in men?
220. What’s one thing you’ve been working on that you feel is keeping you from happiness?
221. If your best friend spoke to you like you speak to yourself, would you still be friends?
222. Do you consider yourself in charge of your life journey or are you more of a passenger?
223. What does a successful life look like to you?
224. What’s something important in your life that you’re looking forward to right now?
225. What can you do now that you weren’t capable of 5 years ago?
Getting to know women over text is somewhat of an art form in itself. Some days, conversation will go smoothly and you won’t have to think about it. Others, it’ll feel forced.
If you feel as though your text conversation is getting dry and boring, these funny questions are ideal.
Go ahead and drop one of these funny/interesting questions into your conversation and see how she takes it. Even if she laughs at how silly the question is, that alone changes the tone of your conversation.
Try it for yourself and see how easily it works!
It’s a simple question but the answer speaks volumes about how she views herself.
C’mon, dogs are unconditional love. Clearly they’re the superior choice.
What kind of monster likes smooth peanut butter anyway?
The perpetual Billy Madison or the legend himself?
Just when you thought “baby” was cringy enough. . .
It seems some actors just aren’t as great as their characters.
Random facts can be a great time!
Get ready for a fun story time. How did she feel when it happened?
Some people would still choose Netflix, just on a bigger TV and couch!
236. What’s the most ridiculous fact you’ve memorized?
237. What’s your most useless talent?
238. How did you hear the truth about Santa?
239. What do you value the most when it comes to choosing close friends?
240. When was the last time you laughed so hard you cried?
241. When you’re at home sick, do you prefer to be left alone or have someone there to care for you?
242. You’re cooking from a new recipe. Do you follow every step or use it as a loose guide?
243. What did you ask Santa for last Christmas?
244. Do you prefer bars and clubs or low key house parties?
245. What’s the last thing you ticked off your bucket list?
246. Are you a night owl or an early riser?
247. What was your favorite movie as a child? Do you still enjoy it now?
248. If you could ask 1 question and be guaranteed an honest answer, what would it be?
249. What’s the next thing you plan to check off your bucket list?
250. What’s the most “adult” thing you’ve bought recently?
Similar to the thought-provoking questions above, these trick questions can be an interesting way to change things up.
Whether you’re on a date, hanging out with friends or even texting, many of these fall into dad joke territory. That means, for the most part, the best response is a groan — perfect!
Again, this may depend on your personality though so that one is entirely up to you. I’m all about the dad jokes so for me, these types of questions get plenty of mileage.
A question that plagues me.
I expect this one will take some thinking.
I see what they did there.
A classic dad joke.
One of my favorite places.
So literal. Well played.
Also feels. You have to watch out for those.
This one’s been a-round for a while.
Well, assuming it’s the right time of day but let’s not be pedantic.
Yeah, English can be complex.
261. What’s always coming but never arrives? (Tomorrow)
262. What gets wetter the more it dries? (A towel)
263. A person fell off a 50ft ladder but didn’t get hurt — how? (They fell off the bottom rung)
264. Is it legal for a man to marry his widow’s sister? (No but he won’t mind, he’s dead!)
265. What can be broken but can’t be picked up? (A promise)
266. What never asks a single question yet always gets answered? (A phone)
267. What has a head and a tail but no body? (A coin)
268. What can you hold without touching it? (A conversation)
269. What starts out tall but grows shorter the longer it stands? (A candle)
270. What has a neck but no head? (A bottle)
271. What starts and ends with an ‘e’ but usually only has one letter? (An envelope)
272. What gets bigger the more you take away from it? (A hole)
273. What goes up but can never go down? (Age)
274. What word is spelled incorrectly in every English dictionary? (Incorrectly)
275. We see it once in a year, twice in a week, and never in a day. What is it?
First dates work best with a particular type of question. You’re both there getting to know each other better but you also don’t want things to feel too serious.
What you’re really aiming for on that first date is to prompt some story time (both ways). Why? Because it makes for easy conversation that allows you to infer so much about each other.
Think about it this way — if she asks you where your last vacation was, the answer is simple, right? That basic question also gives you a host of tangents to talk about. What you did, what you saw, fun adventures, etc.
That’s the type of response you’re looking for with these questions too. Easy!
If you haven’t, you should. You’ll either be great at it or have a great time laughing at yourself!
With over 2.5 million apps out there, you might come across some great ones.
We all have that one relative, right?
There are creative people and there’s the rest of us. Which one is she?
Enough dad, we’ve all heard this story before. . .
Peeling ginger. So many nooks and crannies.
Time for an interesting vacation storytime, no doubt.
Let’s keep on the vacation train. They make for easy and interesting conversation.
Exploring beyond the tourist traps is the best way to see and try new things.
This is a great way to find out what kind of impression you made.
286. What type of music can you absolutely not stand?
287. What’s your favorite ethnic food?
288. Which country did you enjoy traveling to the most?
289. What job do you think you’d be horrible at? Why?
290. What was your first impression when you saw me compared to my profile?
291. What’s the most spontaneous thing you’ve ever done?
292. Did you ever get hooked on a book series growing up?
293. What do you spend most time in outside of work? Heels, sneakers or flip flops?
294. Who is the happiest person you know? Why do you think that is?
295. Have your parents ever tried to set you up on a date with someone?
296. If you had to move to another country next week, where would you move to?
297. What random topic are you really passionate about?
298. What country have you always wanted to visit but never got around to?
299. What’s the best compliment you’ve ever received?
300. How would you react if I kissed you right now?
The classic “Would You Rather” scenarios. These really are just designed to be funny questions for an easy laugh. Less about getting to know her in a serious manner, they do a great job of keeping up that level of humor.
The thing I love about funny questions like these is that they can be used in just about any context. Mid-way through your first date, walking to your next location, text message — everything goes.
They’re just silly throwaway questions, which makes them so versatile. Go ahead and get creative with them. You can even throw in some sweet things to say while you're at it.
This is actually a hard question. Aren’t dogs already perfect?
Either one would be so intriguing. Do humans ever move to another planet?
Think about it — no more traffic ever again? Sign me up!
1,000 years is a long time. Too long, perhaps?
Taking that earlier question to the extremes. Both are possible if that’s your thing.
Red lights seem to love me, so I know which one I’m choosing.
Some people just aren’t cut out for the big wide world. Others go stir crazy spending too long in one spot.
Now this is a tough decision. Both would be so helpful to daily life.
Sorry, what was your name again?
They’re kinda the same thing in a sense. The question is, which would be worse?
311. Would you rather only eat meat or only eat vegetables?
312. Would you rather have a Texas accent and live in New York or a New York accent and live in Texas?
313. Would you rather be an average person today or a world leader 2000 years ago?
314. Would you rather live in a house on the beach or a cabin in the mountains?
315. Would you rather have a dragon or be a dragon?
316. Would you rather nobody show up for your wedding or your funeral?
317. Would you rather have a golden voice or a silver tongue?
318. Would you rather your own mode of transport be a giraffe or a donkey?
319. Would you rather always be the funniest person in the room or the smartest?
320. Would you rather be dumb and attractive or smart and ugly?
321. Would you rather spend the rest of your life on a sailboat or in an RV?
322. Would you rather always be 20 minutes early or 20 minutes late?
323. Would you rather always speak your mind or never speak again?
324. Would you rather search engines were taken down or all social media?
325. Would you rather lose your best friend or lose everyone but your best friend?
Sometimes, the best way to shake things up in a conversation is to throw in some weird questions. Something that comes out of left field that she may not have been expecting.
These are far from the deep or thought-provoking questions above. Instead, they’re about changing the tone of your conversation and making her laugh.
The other great thing about these questions is they keep you well and truly safe from the mundane. If you sat there asking cookie-cutter questions the whole date, that feels boring and forced very quickly.
Instead, it’s unlikely she’s heard any of these before, which is a major help in itself. Have fun with them.
Oh boy, this date is about to get interesting.
The Office or Friends? It’s usually one of the two.
That’s right, you didn’t realize your cat was keeping tabs, huh?
Pay attention to this answer. It’ll help decide on a movie to watch together.
Again with the important questions.
Time for her inner deviant to come out.
There’s so much we still don’t understand about the world. This could get interesting.
Besides you, of course.
Damn nature, you scary!
336. If you could have any animal as a pet (and it was ethical), what would you choose?
337. What movie or series do you quote the most?
338. What are you best known for amongst your friends?
339. What song are you playing to death right now?
340. What’s something I should try at least once this year?
341. What wild experience have you done that surprises people?
342. After a big day, do you prefer alone time or socializing?
343. If you had to get a quote tattooed on you tomorrow, what would it be?
344. What’s the best restaurant experience you’ve ever had?
345. Where do you spend your time when you’re not at home or work?
346. If you could live to be 100 would you rather your mind or body stay the same as it is at 30?
347. What’s the strangest thing you’ve ever eaten and actually enjoyed?
348. If you never had to sleep again, what would you do with that extra time?
349. What household task do you hate the most?
350. What current phase do you think we’ll laugh about in 20 years?
These random funny questions are also going to serve you well on your dates and texting afterward. Any time you feel like the conversation is getting boring or you don’t quite know how to respond, drop one of these in.
It can be a funny change up and just what your conversation needs to go from low priority to engaging. We’ve all been there before, right? You’re texting a woman and it’s starting to feel like a real chore to respond?
You never want to be that guy in any situation. Keep these random funny questions up your sleeve.
For real. Is it even possible to like both equally?
Ugh, popcorn. One does not simply have one serving and call it a day.
Sounds very inconvenient. Imagine those big meetings at work?
You’re about to hear a hilariously terrible crush and it’s fantastic.
There are endless ways this one can go. It might also tell you a little about what she enjoys doing.
Bring on the nostalgia.
The ability to really communicate.
Not tequila. Please don’t say tequila.
There’s no wrong answer here, we all have our struggles and goals.
This might sound like a joke but it’s important to know!
361. Do you prefer a stable, consistent job or one where your income is tied to your performance?
362. Where was your favorite vacay destination growing up?
363. What’s the biggest thing that’s changed about you since high school?
364. What expensive product do you buy that’s worth every cent?
365. What’s your most embarrassing story from your school years?
366. What’s one job you think everyone should have at some point in their life?
367. What’s your favorite comfort food after a bad day?
368. Have you ever had to do any public speaking? How did it go?
369. If you could only eat fast food for a month from one store, which would you pick?
370. What’s the most amusing fact you know?
371. Have you ever been to a Meetup event?
372. If you saw a friend from high school tonight, would they recognize you?
373. Do you take regulation vacations or save up your vacation time?
374. If you could change one type of food or drink to be healthy, which would you choose?
375. What’s the strangest way you’ve made a new friend?
Last but not least, some funny dares to ask a girl. Once you’ve established some comfort between the two of you, these low-commitment dares are a fun task to throw into the mix.
They’re simple enough that she’s likely to complete them. If she’s the type, this just might start a back and forth of fun dares — what a great way to pass your time. That hardly sounds like a boring date, huh?
The key to using dares in your date is to keep that balance between fun and “too far.” If it’s too much, she’ll probably back out. If the dares are boring, it kind of defeats the purpose.
It’s a great look, for sure.
Your date is about to escalate in the best kind of way.
Such a great way to see what works for her.
Just how much of a deviant can she really be?
How cute. Better make sure it’s a good pic!
What a classic yet harmless dare.
Pleeeeease don’t make it valley girl.
There’s no way this one is anything but hilarious. Ready your best Gordon Ramsey impression.
It’ll go great with that Sharpie’d tooth.
New artist? What do you mean?
386. Do 60 seconds of intense salsa with a broom
387. Dial a random number and chat to them for 2 minutes
388. Write an important secret on your body in permanent marker
389. Record yourself singing a made-up song and send it to me
390. Do a sexy dance on one leg
391. Draw yourself a unibrow and take a cute selfie
392. Film yourself doing the chicken dance somewhere visible — send me the video
393. Let me give you a 10-minute makeover
394. Tell me about your biggest sexual fantasy
395. Send me a link to the last thing you watched on YouTube
396. Record your best celebrity impression and send it to me
397. Send me the least flattering photo you have of yourself on your phone
398. Give an inanimate object a lapdance for 60 seconds
399. Draw a handlebar mustache on your face with a permanent marker
400. Take a screenshot of your search history for the last 2 days