20 Questions to Ask a Guy You Like: Funny and Interesting Questions for Getting to Know Someone

Updated on June 26, 2017
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Jorge's relationship advice is based on experience and observation. He's seen many people—including himself—get seduced and hurt by love.

Questions to Get to Know a Guy

Part of the fun of getting to know someone new is the mystery involved. You don't know much about him, so every little detail that you discover is something exciting and novel.

Occasionally, you might run out of things to talk about, though, and you may not know what to ask next. If you really want to get to know a guy, then consider asking him some of these 20 questions. It will be fun to hear his answers, but each of them will also give you a bit of information about his personality:

Question #1: Have you ever been in love?

This question is a pretty common one and will help you get to know his stance on love. If he's never been in love before, you might be dealing with a guy who isn't too romantic (or who is perhaps too young to have experienced love).

For some people this isn't a problem, but if you like all of the mushy and romantic aspects of a dating relationship, then you might want to take his lack of interest in love into account.

Getting to know a guy can be as easy as wandering around and asking him the right questions.
Getting to know a guy can be as easy as wandering around and asking him the right questions.

Question #2: If you could only have one possession, what would it be?

This question will tell you what his values are when it comes to material possessions. What's most important to him? Is it his car? His clothes? Other random things?

Does he have a possession of sentimental value that means a lot to him? If so, this can actually open the door to a lot of other interesting questions. You might ask him what this possession means to him.

Question #3: If you could live on another planet, would you? Which planet would it be?

Is he very tied to this Earth, or does he have his head in the clouds? His answer to this question could also clue you in as to whether he thinks that he adapts well to new environments. Consider this if you ever want to travel outside the country with him.

Maybe he'd like to be your sexy astronaut.
Maybe he'd like to be your sexy astronaut.

Question #4: What is your idea of the perfect mate?

Naturally, this is a very obvious and leading question to ask a guy. If you already have a romantic vibe going, it will hint that you like him, no doubt.

If you're okay with that, go ahead and ask. Listen to his answer carefully, as this will give you clues about your possible compatibility.

Question #5: What is your most vivid memory from childhood?

Again, this is another way of finding out what's important to him. Oftentimes we remember most vividly those moments in childhood that affected us for the rest of our lives. How did that memory contribute to who he is today? This will give you some idea of what makes him tick and help you to get to know him better.

Question #6: What is the funniest dream you've ever had?

We all have weird dreams once in awhile. By asking this question, no only will you get a laugh, but you'll be able to peer into his subconscious a bit. We often dream about the things that are constantly on our minds.

Was his funny dream about school? Was it about sex? Was it about losing all of his teeth?

Ask for the details and offer your own funny dream memories in return.

Weird dreams can be a window to the subconscious.
Weird dreams can be a window to the subconscious.

Question #7: What's more important, finding the meaning of life or living a happy life?

This is another interesting question to ask a guy that can lead the conversation down all kinds of rabbit holes. The key here is to figure out if your values align. You might also want to ask yourself if you prefer to know painful truths, or if you just want to be blissful in your ignorance. These are two different styles of being, after all.

Question #8: If you ever met an alien who could speak English, what would you tell him?

Another seemingly funny question that has a deeper meaning, this one will let you know how he feels about people and creatures that he considers "other." Is he welcoming of the aliens? Does he come in peace? Does he want to tell them useful information, or does he want to lead them into a trap?

Question #9: What is your funniest memory from college / high school?

Reminiscing can be fun, especially if it's about our wackier escapades. Ask him about the crazy things that he did in school, and you might just learn all kinds of things. It will give you a deeper sense of what he finds amusing and what kind of risks he was willing to take in the past for a laugh.

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Question #10: What are you most afraid of?

Is he afraid of spiders? Snakes? The idea that his life might be meaningless? Maybe he's afraid of his mom, like many people.

Talking about ones fears can be oddly relieving for a lot of people. It will also help bring you closer together because you're sharing the intimate details of your mental landscape.

Question #11: Have you ever been in a fight? If so, why?

You might be curious if the guy you like is disagreeable or prone to violence. This is a good opportunity to ask, in a non-judgmental way, if he likes to fight people.

Some guys will beat their chest and say, "Yeah, all the time."

Others will mumble about one or two instances and preface it by saying that the fights were stupid.

There's no reason to necessarily be alarmed if he relays a few stories in his past where he got into meaningless fights. Most guys get into at least a few when they're teenagers. It's part of being hormonal, confused, and pimply-faced.

On the other hand, if he seems particularly brutal and callous about hurting other people, these are red flags.

Some people are paralyzed by their fears, even the irrational ones.
Some people are paralyzed by their fears, even the irrational ones.

Question #12: What is your silliest phobia?

This is similar to asking about his fears, except you're asking specifically about his dumb ones. Is he afraid of ghosts, even though he thinks that they don't exist? Is he irrationally afraid of clowns? Does the possibility of germs on random doorknobs make him sweat a little?

If he seems hesitant to answer, offer a few of your own irrational fears first.

Question #13: What is the bravest thing you've ever done?

This question will give the guy you like a chance to brag, which he'll welcome if he likes you, too.

You can also get even more information about his values depending on how he answers. Did he relay a story about his physical prowess? Did he talk about how he went skydiving? Did he make up a probably bogus story about how he saved a dozen children from a burning orphanage? Or did he mention overcoming an obstacle that was more mental, like breaking a life-long addiction?

Question #14: If you could change one thing about your body, what would it be?

This will let you know how he feels about himself physically. If he says that he wouldn't change a thing, ask him why. He could be bragging and trying to hide his insecurities, or he could genuinely be unconcerned with his physical appearance (which is rare).

Question #15: What is your most important quest in life?

If we're going to assume that life is a grand RPG, then what is his singular most important quest? This will help you to get to know this guy's mission. It will give you some insight into where he is headed in life.

Question #16: Coffee or Tea?

You have to know of course. If he picks the wrong one, it could be a deal-breaker. Tea lovers and coffee lovers don't mix; you may as well be from different political parties. Just give up right there if his answer is wrong. Dump him. Get to know another guy.

If you're not a fan of caffeine one way or the other, then you could always ask if he's into beer or wine.

A polarizing topic.
A polarizing topic.

Question #17: How do you envision yourself as an old, decrepit man?

This says a lot about his future plans and his own self-perception. If he keeps moving along the path that he's in now, where will he ultimately end up? If you're looking for a long-term relationship, this can be especially relevant.

Question #18: What is the first thing you think about in the morning?

Usually, the things that float around at the top of our brains when we first wake up is a clue to where we spend our mental energy during the rest of the day. This question will give you some insight into what he really cares about on a practical, day-to-day basis.

If he just answers with, "That I have to pee," then ask him what he thinks about after he pees.

Question #19: If there was a zombie apocalypse and there were no other humans on Earth, what would you do with your time?

Weirdly enough, this question will help you get to know the core of his passion in life. If there's no reason to work for money, no reason to please others, and no one in the world to interrupt his progress, what would he do?

Question #20: Would you rather be immortal or have super powers?

Finally, this question will let you know a bit about his style of living. Does he favor a slow and steady approach, or does he want to blast his way through challenges? Does he want to seek a longer, healthier life, or does he want to have more power? On the other hand, it might also give you some insight into whether or not he's afraid of death.

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Questions & Answers

    © 2017 Jorge Vamos

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