Weird Questions to Ask a Guy


Few things can bring two people closer together than a mutual goofiness. For many couples, learning to laugh and be playful with one another is a surefire way to fall deeply in love. Though sharing your weirdness with a partner can be scary at first, the reward of finding out that they share your oddball sense of humor can far outweigh the risks.

If you’re ready to introduce the goofy side of you to your partner, we have some advice. First, you need to understand why these types of conversations can bring you so close, and then you need to understand what kinds of questions are likely to have the best result. Below, you’ll find our full list of weird questions to ask a guy. You’ll also find information on how (and why) to ask them.

The Power of Conversation

There are a lot of things that can create intimacy and understanding in a relationship, including shared experiences and shared goals and beliefs. That said, there is incredible power in the art of conversation, and – for many couples – talking to one another is the best way to get closer. Even science will tell you that the couples that spend more time chatting tend to have fewer problems and stay together longer.

At the same time, many women lament the fact that they don’t have any sort of meaningful conversations with their partners, and fear they can’t turn the situation around. Luckily, it’s never too late to begin having more meaningful conversations with your significant other. Best of all, “meaningful” conversations don’t always have to be about serious topics.

What’s the Point of Asking Weird Questions?

Ask anyone with a weird side, and they’ll tell you that few things are as amazing as finding a partner that shares your odd passions and pursuits. For women, in particular, seeing a guy drop his “cool” exterior and be goofy is both endearing and sexy. Still, there are all sorts of other reasons to ask these types of questions. Such as:

They Can Be Flirty

If you’re still in the “getting to know you” phase of your relationship, you can use weird questions to spark more than just conversation. In a lot of cases, questions like these have a flirty component that will get your partner’s imagination revving. The best part is, you can control what direction the conversation goes in depending on your comfort level.

You Can Get To Know Each Other A Lot

Even if you’re romantically involved with a person, you never really stop getting to know them. That’s the beauty of questions like these. Whether you just met or whether or have been married for years, if you’ve never tapped into each other’s weird sides, you can still find out lots of surprising things about each other.

You Can Discover How Compatible You Are

While there are hundreds of different ways for a couple to be compatible, there’s no denying that asking a guy weird questions is a great way to find out if the two of you mesh. Now, if you start asking him questions on this list and find that he doesn’t share your sense of humor or get your references, it’s not necessarily a reason to break it off. Still, at least you’ll know!

You Can Spark a Lot of Conversation

As with all questions, the ultimate goal is to spark conversation. In a lot of cases, weird questions like the ones on the list below are a great way to start a discussion without having to get deep or “heavy.” In short, questions like these are just a fun and exciting way for you to interact with someone you like.

You Can Create “Inside Jokes”

Inside jokes are the glue of fun, long-term relationships, and can result in hours of laughter over months or years. By having secrets that only you and your partner understand, you can end up becoming much closer. With fun, weird, goofy questions like these, you are much more likely to spark the type of jokes you can laugh at forever.

Weird Questions to Ask a Guy

Now that you know the importance of letting a little bit of looney into your dating life, we’re going to go over some weird questions to ask a guy in your life. What will they reveal? There’s no telling until you ask. That’s the fun of it all!

Who Would Play You in a Movie About Your Life?

This example may not seem like a particularly weird question to begin this list. Still, the sheer number of conversational pathways this question can lead to make it an excellent discussion starter. Not only will you likely find out about your man’s favorite celebrities, but you’ll also discover how his knowledge of pop culture compares to yours, which can be a great indicator of how well you’ll do on future dates.

One of the best ways to keep this conversation going is to counter his portrayal of him with someone you find better. If you’re feeling particularly charming or playful, you can counter with someone you suspect he might find slightly off-putting. Either way, the more questions you ask, the more fun the two of you will have with this offbeat topic.

What Do You Miss the Most About Being a Child?

Though it might seem a bit odd (that’s the point, after all) to drop a question like this into normal conversation, the answer can provide immense insight into what your partner thinks about their life and the modern world around it. It also serves as a great “getting to know you” question, as you will almost undoubtedly learn loads about their upbringing and childhood in just a short amount of time.

What makes this question so great is that it can provide a glimpse into an overall philosophy about life and the universe without the conversation having to get too deep. It also allows the two of you to compare and contrast childhood memories, which is always an excellent way to get to know someone better.

What Three Things Would You Bring to a Desert Island?

Another classic date question, this is one can provide loads of insight into your partner’s likes, dislikes, and passions (not to mention their vacation preferences). For many, the idea of having to limit one’s possessions to three must-have items is fodder for excellent conversation. Of course, depending on the type of person you’re dating, they make the question to be more survival-based.

Topics like these, which have such open-ended interpretations but still require an answer, are always a great way to get to know someone better. It’s weird, but fun. Most people won’t hesitate at all if it’s brought up in any conversation, and it’s a top that can last the entire night!

Do You Believe in (Ghosts, Aliens, Bigfoot)?

So just how weird is weird enough? A question like this one can really put your relationship to the test. Of course, talking about the supernatural can lead you down some exciting conversational paths, but if you keep an open mind and listen to your partner, you can have a lot of fun with the topic. From ghosts and aliens to bigfoot and the Loch Ness Monster, everything is on the table for discussion.

The best part of this question is that it allows the two of you to be weird together, but it doesn’t introduce any judgment into the situation. That is – unless one of you has particularly strong opinions about the supernatural. It also allows for interesting “one time, my Uncle…” type stories, which can push the conversation on for hours.

With What Celebrity Would You Most Like to Get Trapped in an Elevator?

While celebrity questions aren’t necessarily weird in and of themselves, the bizarre situation of being trapped in an elevator with someone is almost always entertaining. Depending on the type of person your mate is, he might take a lot of different approaches to the question. Will he choose someone funny, a person who might help, or a person he thinks is sexy?

As with all of these questions, the ultimate goal is to learn more about how your SO thinks. Of course, you can also glean information and what sort of things interest them. Celebrities are “larger than life” people that almost all of us admire to some degree. Even if he isn’t the “celebrity gossip” type, he should at least have some sports heroes or singers he likes. Once you get talking about your favorites, the conversation can go on for hours.

What Would Your Last Meal Be if You Were on Death Row?

Sure, it’s a little morbid, but what subject has more potential to unite two young lovers than the topic of food? Finding out what your boyfriend’s preferred last meal would be can provide a lot of insight into who they are. Will they revert to childhood for their Grandma’s mac ‘n cheese? Will they opt for a sophisticated four-course sushi platter? Or, will they try to cheat with a never-ending buffet?

The best thing about this question is that it gets the two of you talking about a subject that everyone loves: food. By the time the discussion is over, you’ll know some of your beau’s favorite food items, and he’ll understand some of yours. From here, you can start planning more dinner dates, or even plan to cook for them at home.

What Meal Would You Never Eat, Even if Someone Offered You $1000?

Of course, knowing what someone loves to eat and knowing what someone hates to eat are just as valuable when it comes to getting to know one another. While $1000 isn’t a life-changing amount of money, it’s fair to say that it should entice almost anyone to take a bite of a dish, regardless of how much that person loathes it. So, what meal is just too nasty for your man?

Questions like these are invaluable when it comes to building a framework of your partner’s likes and dislikes, which is essential to the long-term success of most relationships. Best of all, they almost often lead to follow-up questions of the same variety. After all, what else wouldn’t your boyfriend do for $1000? Wouldn’t you like to know?

In What Time Period Would You Most Like to Live?

Everybody tends to romanticize specific periods in history, assuming that they might fit in better if they were born in the year X instead of the year Y. More so than almost any question on this list, this topic has the potential to result in long, deep, insightful conversations, all while being weird enough to allow for some goofy scenarios as well.

Perhaps your boyfriend sees himself thriving in the Old West. Maybe he’d rather be a Viking? Perhaps he’d like to go back and meet some of the world’s most influential religious figures? Regardless of the answer, you’re going to know a lot more about him when the discussion is over.

If You Could Meet One Person From History, Who Would it Be?

Similarly, to the last question, this one entices your partner to think of one person from history they’d like to sit down with and have a discussion. If you’ve ever wondered how intellectual your mate is, this is one of the questions that will provide an answer. Will it be tea with Abraham Lincoln or a beer with Teddy Roosevelt? The response may allow you to pick their brain for hours afterward.

What’s Your Favorite Part of the Female Body?

The brilliant aspect of this weird, unusual question is that it’s flirty enough to make men blush, but will seldom result in a sexual answer. Men are clever, and they’ll often make sure to surprise you with the type of response you’d least expect. From lips to ears to the small of a woman’s back, you’ll be chomping at the bit to find out what they pick.

As we mentioned before, being able to be weird and flirt at the same time is an essential skill in the dating world. After all, you’re not only giving your partner a look into your inner goofiness, but you’re also positioning yourself as a strong, confident woman who knows what she wants. Of course, as women, we love to hear the answer to this question for romantic reasons, as well.

What Country Would You Live In if You Could Choose Any One?

More so than ever before, people are dreaming of traveling to faraway lands and experiencing new cultures and societies. As a result, many people are also fantasizing about relocating to other parts of the world and living out their days as an entirely different version of themselves. Ask a guy this question, and the answer will provide you with endless insight.

This question is almost always going to result in a huge influx of information about your partner. In one fell swoop, you can learn all sorts of things about the type of political system they prefer, the type of culture they feel comfortable in, and likes and dislikes like food, climate, and environment.

What Is Your Weirdest Turn-On?

Here is another question that is nice and flirty without being too overt. In almost every situation, your guy’s response will be more playful and fun than it will be sexual. Perhaps he really likes it when a woman wears a white button-down shirt? Maybe he thinks it’s hot when a woman does outdoorsy stuff like hiking or rafting? The discussion will be fun, and the info will be invaluable.

Remember only to ask flirty questions like these if you’re confident in steering the conversation in that direction. At the end of the day, these questions are supposed to be fun, not pornographic.

Can You Make Any Impressions?

Keeping a conversation light and fun is essential to a good date, and this question certainly fits that criteria. No matter what the impression is and how good they are at it, this offbeat question is sure to get a conversation going and almost guaranteed to result in laughs. As a bonus, you could ask him to make an impression of you as well.

What’s Your Favorite Joke (Dirty or Otherwise)?

The great thing about trading jokes is that you discover a lot about what makes your SO tick. Not everyone is into the same type of humor, and this is an opportunity to see what makes your boyfriend double over with laughter while simultaneously showing him what you find funny.

Believe it or not, humor is a valuable thing to have in common. Not only does it help you choose movies that you both will enjoy, but it also allows you to attend comedy shows or improvs together – which can make for perfect date nights. On the other hand, finding out that your beau into dirty, inappropriate humor, while you like clean observational humor, will at least help you identify things to avoid.

Would You Rather Live Somewhere with Permanent Winter or Permanent Summer?

For instance, a winter person might love new-fallen snow, cuddling by a warm fire, and activities like skiing and snowmobiling. A summer person might love bumming around on a beach, drinking cocktails with umbrellas in them, and activities like swimming, surfing, and volleyball. However, you have to make them choose – there’s no honor in cheating!

What’s the Dumbest Thing You’ve Ever Done?

If the conversation that results from this question doesn’t end in laughs, you both need to work on your senses of humor. There are a lot of things that people define as “dumb,” but they’re almost always guaranteed to be entertaining if not a little embarrassing for the person doing the telling.

Seriously though, asking someone to bear their soul this way is a great way to get to know them while also showing them that it’s OK to be vulnerable around you. Best of all, you’ll get to make them feel less embarrassed by sharing some dumb exploits of your own.

What Piece of Technology Are You Hoping Gets Invented Soon?

We all like to daydream about ways our lives can be improved, which is why this question is a great way to spark some weird and wild conversations. While many Gen Xers are still waiting on their hoverboards, your guy might have many ideas about what inventions could prove useful in his day-to-day life. Of course, you should have some ideas of your own to keep the conversation going.

The beauty of this question is that it disguises a value conversation as fun, playful chit chat. By the answers that your boyfriend gives, you can discern what is important to him, and what things he’d prefer just to have done quickly (or done for them). While the question may seem superficial at first, it can offer a lot of insight into your partner’s personality type.

What Is the Strangest Fact You Know?

This is a question that’s almost certain to end in hilarity, or at least with the two of you trading weird facts long into the night. Most people have some pretty odd information rattling around in their brain, and chances are they rarely – if ever – get a chance to impress someone with it. So, if you’re the type of person who loves a laugh and some useless information, this is the question for you.

What Did You Learn?

Now that you’re armed with a laundry list of weird questions to ask a guy, all you need to do is go out there and ask them. Remember, don’t use them all in one night, and don’t push too hard if the conversation starts going into a sensitive area. Afterward, you can evaluate what you learned about your partner and – hopefully – feel much closer to them.

In the end, the goal of weird questions is to allow your partner to see your free-spirited, goofy side (and to see theirs as well).


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