Use These Deep Questions (To Ask a Guy) and Watch Him Get Serious and Personal With You!

If you’re looking for fun, lighthearted conversation topics well … you came to the wrong place. (Go here if you want fun questions to ask.)

If you want to get to know someone on a deep, profound level, then we’ve got exactly what you need.

Most people shy away from the deep stuff and as a result, most connections are surface level and superficial at best. The way to really connect and get to know someone is to go deep.

MORE: The Ultimate List of Questions to Ask a Guy to Get Closer

These questions range from personal to philosophical. Some may bring up painful memories, others are mind-benders that are just interesting to think about.

Just know your audience. If it’s a guy you have a crush on that you don’t know so well, you may want to go with some of the more neutral questions. If it’s someone you connect with deeply, then these questions can help you take it to the next level.

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This Or That Questions Game

Whether you want to get to know someone better or pass some time, this or that questions are a Loy of fun.

The questions are innocent enough that no one will feel embarrassed or uncomfortable. At the same time, you can learn a lot about someone! You can play it as a game with a group of people, or one on one with a guy you’re into. To play as a group, give everyone a coin (or anything that can be turned upside down) and have everyone put the coin up if they think it’s the first option, and down if they think it’s the second.

MORE: The Ultimate List of Questions to Ask a Guy to Open Him Up

To play one-on-one, just refer to this handy list of the absolute best this or that question and take turns asking each other. You can also try to guess what the other person will say. It’s sure to bring on a lot of laughs, and maybe even steer you into some interesting conversation.

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The Very Best Questions To Ask a Guy You Like

Talking to your crush is scary. You can freeze up and be reduced to a stumbling, bumbling fool and that’s not so sexy. On the one hand, you want to impress him. On the other, you don’t want to come across desperate or awkward.

Knowing the right questions to ask will make you cool confident and seem effortlessly charming. Why? Because people love talking about themselves! You don’t need to tell your crush about all your dazzling accomplishments. What will really win him over is if you ask meaningful questions and really listen to his answers. It’s as easy as that.

MORE: The Ultimate List of Questions to Ask a Guy to Get Closer

However, you need to take some precaution. You don’t want to seem prying or obtrusive, so I came up with the ultimate list of questions to ask your crush.

These questions are innocent enough, but will still evoke revealing answers that will help you get to know him better, breaking that barrier and forming a deep connection.

It’s best to keep the conversation positive and light. You don’t want to dig too deep into his skeletons and emotional traumas. There is plenty of time to get into all that stuff, but if you’re in the early stages of a relationship, or if this is a guy you’re hoping to be in a relationship with, then keep it fun and upbeat.

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Ever get the tongue-tied feeling when talking to a guy you like? Do you dread those awkward silences that tend to creep in and wish you knew fun, interesting ways to keep the conversation going?

Well, look no further! You’ve come to the right place. When getting to know a guy you like, it’s important and very handy to have an arsenal of interesting questions to ask him, questions that go beyond “So what did you do today?”

A lot of people have a hard time connecting in an authentic way. We hold ourselves back, maybe because we don’t know how to get in there or maybe as a protective measure, and a connection can hit a wall at a certain point as a result.

MORE: The Ultimate List of Questions to Ask a Guy to Get Closer

To help you break through that barrier and really get to know someone, we’ve come up with the ultimate list of cute questions to ask a guy you like.

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In the age of texting as a main mode of communication and using emojis and memes to express how we feel, it’s getting harder to build a deep connection. A lot of us are afraid of vulnerability and there are certain places we just won’t go … and few realize that this is the reason so many people have a hard time building genuine connections.

Asking the right questions can push past someone’s walls and get them to open up. You can learn a lot about one another and really form a deep bond and really get to know someone.

MORE: 225 Questions to Ask a Guy- The Ultimate List 

The following list includes all types of personal questions. Some are fairly mild and others really get in there. Pick and choose what you feel comfortable with, and what you think your guy will be comfortable with. The most important rule is to not push too hard. Know when to back off and let it go when he doesn’t feel comfortable answering something, even if you might really, really want to know the answer.

And with that, here are 50 personal questions to ask a guy to get him to open up:

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You will find tons of content on how to tell if a guy likes you here on A New Mode. The reason? It’s probably the number 1 question women have when it comes to dating and relationships.

We’ve all been hurt in the past, many of us have experienced the pain of wanting someone who doesn’t like us back. And it hurts. It’s hard not to take it personally.

MORE: How to Know If a Guy Likes You For Sure

Sometimes it’s clear as day when a guy likes you, other times it’s a little hard to tell. He seems like he’s interested, but it’s hard to be totally sure, and you don’t want to come right out and ask him and risk embarrassment or rejection.

That’s why we’ve created this handy list which includes every sign that a guy definitely likes you. You have to take the full picture into account. If he’s showing maybe 1-2 signs then he probably doesn’t have strong feelings for you, he may be somewhat interested. If you find yourself checking yes to most of these, then he definitely likes you.

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Texting is our main mode of communication these days- it’s just the way it is, so much so that when someone actually calls you think there must be an emergency.

Asking the right questions can really open the gates for a deep, profound connection. But there is a huge difference between talking in person and chatting via text. When texting, you can’t really ask questions where answers will be long detailed stories, or where there are a lot of nuances.

Texting also isn’t the right forum to have a heavy or deep emotional conversation because a lot can get misinterpreted or lost in translation.

MORE: 225+ Amazing Questions to Ask a Guy- The Only List You Need

Texting isn’t the time to get someone’s full life story, but you can still learn a lot about another person … when you know the right questions to ask,  questions that are little more creative than:“Hey whats up?” and  “How are you today?”

And with that, here is my compilation of the absolute best questions to ask a guy (or girl) over text.

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Conversations have a way of becoming quite dull- maybe it’s because the art of conversation has mostly been lost in the digital age of hiding behind our screens and communicating via gifs and emojis.

Asking the right questions is a powerful way to galvanize a conversation and create a connection. These fun questions cover a range of topics and are great for asking a guy you like, a guy you’re dating, a friend, a co-worker, anyone really!

MORE: The Ultimate List of Questions to Ask a Guy to Get Closer

Some questions will reveal shocking information that may surprise you, some will bring out a hilarious story or maybe an embarrassing moment, some may open the door for deeper conversations.

Either way, they will steer you into interesting new directions.

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Everyone loves to laugh, that’s just a given. Humor is a great way to connect with anyone- from a guy you’re seeing to a friend to an employer. It is one of the best ways to bond and just let loose and have some fun.

Being funny comes easily to some people, and is not as easy for others. And everyone has a different scene of humor. Some people are silly, some are raw, some have a dry sense of humor, some have a perverted sense of humor, different strokes!

You don’t need to be a natural comedian to be funny. Sometimes asking the right questions can lead to some belly-aching laughter.

MORE: The Ultimate List of Questions to Ask a Guy to Get Closer

To help you connect with a guy, or anyone really, using a little laughter, we came up with a list of the best funny questions to ask. They’re pretty universal, but you should also use your judgment and tweak as needed based on your relationship and the person’s sense of humor.

These questions are open-ended enough to spark some great conversation. You can either slip these questions into a conversation or tell him you found an awesome list of funny questions to ask someone online and why don’t you give it a try?
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The 21 Questions game is a fun and easy way to get to know someone. The rules are pretty simple. You just ask someone 21 random questions and enjoy finding out the answers. Then they can follow by asking you 21 random questions.

You can play it in a group, but I personally think it’s much better one on one, or maybe with three people max. If you go beyond that, it can get a bit tedious. The best way to play if you are going to do it as a group is to just go around the circle with each person having to answer one question.

But like I said, that’s not as fun. Games like Truth or Dare or Never Have I Ever or Would You Rather are much better suited for groups.

MORE: 225 Amazing Questions to Ask a Guy

21 Questions is the perfect game to play with a guy you like, I think it’s the ideal. It’s a great way to break outside the typical flirty banter and really connect on a deeper level.
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It seems like pulling off the “cute” look comes naturally to some women. For those who have a harder time with that particular look, it can be bewildering trying to figure out how they are doing it.

The reason it’s hard to pinpoint is that it’s not just about finding the perfect shoes or styling your hair a particular way. It’s a vibe you send out, and that begins with your mindset.

MORE: How to Be Irresistible to Men

Be yourself, even if there are parts of you that wouldn’t quite fit under the label of “cute.” In fact, some women recoil at the very idea of being “cutesy.”

But some women would love to be perceived as an adorable heart-melter. If this sounds like you, here are some handy tips for upping your “cute factor.”

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Some women naturally attract men, it’s easy and effortless for them. Others don’t no matter how hard they try. So what’s the secret?

It’s not a matter of looks. It’s not always the most traditionally beautiful woman that seems to effortlessly ooze charm. Copying her hairstyle or buying the same brand of mascara isn’t going to do the trick.

In fact, some gorgeous women take great efforts to beautify themselves and still find it difficult to bewitch men in the same way others can. This is because attracting another person goes deeper than that. It goes beyond your physical appearance.

MORE: Exactly How to Seduce a Man

And the good news there is that it means it’s mostly under your control! The mindset that will enable you to do this filters into various parts of your life. It’s not just a matter of changing your lipstick. It’s about a vibe and energy that is effortlessly transmitted.

To learn how to adopt the persona of an easily magnetic woman, the woman who can attract any man, check out the steps below.

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Flirting is one of those things that seems to be second nature to some, but is an entirely foreign language to others. Unfortunately, like with kissing, if you get too “in your own head” about it, it only becomes harder.

Try to remember that flirting is supposed to be fun. Don’t take it too seriously. If you award it too much weight, it becomes downright scary – so relax. (I know, easier said than done.)

A playful, flirtatious banter is like a tennis match. It can feel exhilarating when you get into a good groove with someone. If you’re interested in a guy who is a little nervous, some mild flirting can be the push he needs to make his move.

MORE: Foolproof Flirting Tips

Here are some savvy tips to step up your flirting game.

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The only people in life who don’t have a story about being rejected are unsuccessful, lonely people who have never tried at anything. Anyone who has succeeded in anything has also failed. This is just as true in relationships as it is in business, sports, or any other area where you have to put yourself out there.

Being rejected means you are in excellent company.

Despite knowing that rejection is a part of the human experience, it’s still really tough not to internalize it. It’s hard not to take it personally, even though when we have to reject others in life we hope they don’t take it personally. You can’t help but feel like it’s a reflection of your flaws.

MORE: How to Handle Rejection Flawlessly 

Rejection can come in small packages or grand lessons. It could be as simple as a guy not messaging you back on a dating app. Other times it’s as awful as a long-term partner telling you he doesn’t love you anymore.

Regardless of the cause of the rejection, you absolutely have to learn how to deal with it. If you don’t, you won’t be able to live the full life that you deserve. Here’s some advice on how to do exactly that.

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“You have to kiss a few frogs before you find your prince!”

How many times has that phrase been cheerfully offered after a bad date (or three)? Dating can be so stressful that it sometimes feels like you’re taking a year off of your life every time you put yourself out there. There may be many times when you’re tempted to quit. Times when you want to just call the whole thing off, where you resign yourself to the fact that maybe you’ll just end up alone.

You may commiserate with your single friends by swapping dating horror stories. While these can be comical when told to an audience afterward, living through them is boring, at best. At worst – it’s frightening and sometimes downright torturous.

MORE: The Truth About Playing Games and the Chase

We come up with positive clichés to pass around in the hopes of making the exhausting struggle seem commonplace. Sometimes this works, and other times it just feels more depressing.

But the truth is, there is a way to make dating more enjoyable and to gain from the experience, rather than feeling like you’re losing your dignity and your mind. With the right tips and the right things to keep in mind, you can actually learn a lot about yourself, and maybe even find that special someone.

Here are some tips for navigating modern dating.

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“It is the differences between men and women, not the sameness, that creates the tension and the delight.” – Edward Abbey

Men and women are, undeniably, different. While these differences are something to be celebrated, it can make communication a challenge. It takes empathy and a desire for connection to break through these barriers.

MORE: 5 Things Every Woman Needs to Know About Men

You can’t routinely expect a man to want to hear the same things as you do. What makes you feel happy and loved is not always going to be what does the equivalent for him.

If you’re feeling a little lost about what your man wants to hear, here’s a list of suggestions to get started.

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So you want to know how to get a guy to like you, how to be more interesting and appealing to the opposite sex.

I don’t blame you for any confusion you might be feeling. Most of the information out there on this topic is horribly misguided. It tells you to hide interest, to play games, to make him chase you. This isn’t an effective long-term strategy. Sure, it might pique a guy’s interest, but it isn’t enough to sustain it, and isn’t that the goal? Where did we get the idea that men want aloof women who play hard to get? It’s one thing to have a little mystery around you, but it’s an entirely separate thing to act distant and cold to the man you’re interested in.

MORE: The Top Signs A Guy Doesn’t Like You

Here is a key thing to understand about men: men move toward what feels good. If it feels good to be around you, he’ll want to be around you a lot.

Try to remember this when you are interacting with the guy you like. Being kind and lively is going to serve you well. Being an ice queen, meanwhile, will leave you lonesome. This is the core understanding that underlies all the points in this article.

But let’s dive a little deeper and look at what it takes to get a guy to really like you:

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Much of the time, when a guy likes you he makes it clear and obvious. That’s why it can be so perplexing when you think a guy likes you, but you’re not 100% sure. You don’t want to waste time pining after someone who’s not interested, but it really seems like he’s interested, so you can’t let it go either.

There are a few reasons a guy would hesitate to make a move. It could be that he can’t tell if you like him and he doesn’t want to put himself out there until he has some evidence that he won’t be rejected. Some guys are just naturally more shy and need more time than others to get the ball rolling. Additionally, it could be that he’s not in the right headspace for a relationship.

MORE: These Are the Biggest Signs a Guy Doesn’t Like You

If you feel like you’re getting mixed signals and need help deciphering them, this article will clear up the confusion. Read on for clues that a guy likes you, no matter how hard he might try to hide it.

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Is there anything more relatable than listening to a girl wonder aloud if a guy likes her? That particular human experience is universal. Everyone knows the vulnerability of liking someone. Just the very idea of confessing your feelings is alarming enough to make a team of energetic butterflies swirl pirouettes in your stomach.

MORE: Know Exactly How He Feels (Or Doesn’t Feel) With the 11 Biggest Signs He Doesn’t Like You

Just like women, guys want to do their best to avoid the crush of rejection. Eventually, one of you has to be the first to admit their feelings. To make this prospect a little less terror-inducing, guys will look for signs that you like them beforehand. Sure, sometimes signals can be misread. But a little evidence is better than nothing when summoning the courage to make your intentions known.

Here are the signs that he’s in the process of gauging how you feel about him.

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It can feel hard enough trying to figure out if a guy likes you, but even harder when it comes to figuring out how to tell if a shy guy likes you.

Kids have amusing ways of deducing whether or not someone likes them. These methods might include asking other friends to ask the object of their affection “who they like.” Let’s not forget the classic pulling of daisy petals – “he loves me, he loves me not.” Raise your hand if you also tried to count the petals in advance and rig your chances!

It seems that even as women grow older and wiser, the age-old question of whether or not a guy likes you remains frequently indecipherable. You ask your friends for help as you attempt to decode text messages, and then promptly wonder if you’re reading too far into things. People offer conflicting advice, and the confusion about what kind of signal you’re getting can be enough to make you freeze up.

MORE: 5 Telltale Signs He Likes You

All of this typical back-and-forth becomes even more bewildering when the guy you are interested in is shy. When a guy lacks the confidence to show you how he feels, sometimes you have to do some sleuthing of your own. At the same time, this can feel scary because what if you are trying to see signs where there aren’t any?

Here are some hints to look for when you are wondering if a guy on the shy side is into you.

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Having to navigate the waters of romantic texting is a relatively new predicament. Our grandparents may have occasionally dabbled in poetic letters, but that can’t quite compare to the unique set of challenges that come along with texts.

In some ways, it seems less intimidating to text a guy than to communicate in person. You have more time to think of sharp, witty things to say. If he says something you totally don’t understand, you can consult with your friends before giving an answer. You don’t have to be hyper-aware of your body language, or of reading his.

MORE: The Biggest Signs He Doesn’t Like You

But a lot of the time, texting just makes it harder. Those pesky body language cues are massively helpful – not only for understanding his intentions, but also for making yours known. Humor is harder to portray over text. Worst of all, if you say something dumb, it’s forever in writing. You get to stare at it in panic as you wait an excruciatingly long time for him to text back.

Here are some guidelines to help you text your crush to get the conversation going:

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When a friend asks you for an opinion as to whether or not a guy likes her, it’s probably not too tough for you to formulate an opinion. It’s much easier to gauge this kind of thing when you’re looking at it as an objective third party.

MORE: The Top Signs He Doesn’t Like You

Of course, when it comes to deciding if your own crush likes you, the formerly simple notions blur into a muddling mess. You doubt your own powers of deduction, and for good reason. It is significantly harder to examine a situation fairly when your own emotions are part of the equation.

To make this daunting process a little simpler, here are some key signs that your crush likes you.

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“Being deeply loved by someone gives you strength, while loving someone deeply gives you courage.” – Lao Tzu

Anyone who’s been in love can relate to that flicker (or tidal wave) of panic at the idea of being the first one in the relationship to say it. You know, those three powerful words. You’ve heard them said out loud so many times that they almost lose their meaning. So why are they abruptly terrifying when you try to make your own mouth utter them to a special someone for the first time?

MORE: The Biggest Signs He’s in Love With You

Loving is the most vulnerable thing we do. For something that happens to everyone, it’s surprisingly unique to each person experiencing it. You feel like you’re charting undiscovered territory as you navigate falling in love. Once you feel it, you get the urge to scream it from the rooftops. At the same time, if you haven’t said it to your person yet, even whispering the words seems a task far too daunting for a mere mortal.

To summon the courage to admit your feelings, observe your partner. There are tangible signs that a man is in love if you look for them.

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Unless you’re a secret mind reader, you’ve spent a little time – okay, maybe a whole lot of time – wondering if a guy likes you. Every girl has.

Just like women, men fear rejection. There are many possible explanations for why a guy who likes you hasn’t admitted it yet.

MORE: This is Exactly How to Know if a Guy Likes You For Sure

Being patient when you like a guy can be tricky, but do yourself a solid and take the time to make some observations. Once you have a better idea of whether or not he likes you, then you can decide how you should best proceed.

Read on for the signs that a guy likes you, as well as some advice on what to do about it.

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You and your boyfriend broke up and to add to your pain, he’s dating someone new. Is it for real, or is he in a rebound relationship? (And you desperately hope it’s the latter!)

The world is full of varying and conflicting opinions. What’s one thing everyone can agree on? Easy. Breaking up with someone sucks.

Whether you are the one initiating the breakup or the one being left, it’s just undeniably painful. This universally agreed upon suffering is amplified when you see your former flame in a new relationship. There’s no good way to discover this information.

Scrolling through your social media and coming across a picture of them together is awful enough to make your mouth dry and your cheeks flush. Sometimes it’s a knowledgeable friend that fills you in. Hopefully, you don’t endure the much worse scenario of learning the shocking news by running into the new couple somewhere (and usually it will happen when you’re makeup free, greasy haired, and wearing your old stained sweats because of course, that’s how it would happen!).

MORE: This is How to Get Your Ex Back in 5 Steps (With Testimonials)

Regardless of how you uncover the scoop, you’re bound to be curious about it. Even if you don’t want to get back together, it’s only human to want to know. Are they serious? Or is it a typical rebound relationship? And if you do want to get your ex back, that’s also easier than you might think, even if he is seeing someone new.

Here are some signs that the relationship is not going to go the distance:

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Breakups are awful, and what can make them even worse is when he’s moved on but you haven’t. It may feel like you’re in a rut, stuck in the same place. It may feel like you just need more time to heal. But maybe you’re rationalizing things and deluding yourself into thinking you’re over it when you aren’t even close. If you suspect you haven’t quite fallen out of love, you likely haven’t.

If you think you’re not over him, you may still need further confirmation of that so you can figure out what to do next.

MORE: How to Get Your Ex Back in 5 Steps Guaranteed

Being honest with yourself is the first step. Only after that can you figure out where you’re at and where you want to be so you can begin moving forward.

Here are the signs you’re still in love with your ex.

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“I fell in love the way you fall asleep: slowly, and then all at once.”
Love is strange and mysterious: it can happen in the blink of an eye before we know what hit us, or it can envelop us slowly.
Because it’s not always the same for everyone, a lot of people don’t understand what love truly is. They mistake infatuation and obsession with true love because they can feel the same sometimes. The problem is that when you confuse infatuation with real love, it can mean getting overly invested when you shouldn’t, or spending too much time with the wrong person.

Why would you mix up infatuation with true love? It’s not always easy to tell the difference. Fears and insecurities can get in the way and cloud your judgment. If you’re busy worrying that he doesn’t love you back, or that he’ll never commit, or that he’s going to leave you, you’ll be in your head so much it will be impossible to be in your heart.

MORE: 11 Undeniable Signs He’s In Love With You

Even if you’re not feeling insecure, both infatuation and love cause chemical reactions in us that change the way we think and behave, and that can also cloud our judgment.

Some people say, “you just know,” but that simply isn’t always the case. Sometimes it helps to think it through and know the concrete signs that it’s more than infatuation. If you’re wondering if it could be love, look for these indicators.

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“Nothing ends nicely. That’s why it ends.” – Tom Cruise

Who has ever had a friendly, lighthearted breakup? One where both people calmly and without emotion decided it was time to make a clean break? Closure tied up in a pretty bow?

Not anyone human. Or, at least, not any human coming out of a relationship that held any meaning for them.

Since breakups can be a whirlwind of confusion, betrayal, and heightened emotions of all kinds, figuring out how to proceed afterward can be just as tied up with angst. For the first week, you don’t even recognize the person you are. When you share your life with someone, some of your identity becomes intertwined with them. When they are gone, your whole reality shifts.

What can make that process even harder is when your ex decides to muddy the waters by showing signs he wants you back. You’re left to wonder if he’s just going through the same turmoil of the breakup you are, or if his actions are legitimate.

MORE: How to Get Your Ex Back in 5 Steps Guaranteed (With Testimonials)

If he does truly want to get back together, is that really a good idea? How do you know when, or if, you should act on some of these potential “signs?” Are they even real signs?

For advice on identifying these clues (and what to do about them), read on.

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It’s hard to admit when a guy isn’t serious about you, especially when you really like him. Usually, you’ll feel it in your gut but you’ll avoid facing it. When you’re hopeful about things it’s just easier to make excuses for his behavior and focus on any shred of evidence that he likes you enough to take it to the next level.

The thing is, he can like you but not want to be in a serious relationship with you. This is why so many women get confused.  Just because he wants to spend time with you … he keeps asking you out … he stays in touch and sends you sweet texts every day … this doesn’t mean he’s serious about you. These things mean he’s into you, but they don’t necessarily mean he sees a long-term future with you.

The only way you can tell if he’s serious or not is to be objective when it comes to your love life. This is a tough skill to learn, but it’s very important and can save you from endless heartache.

MORE: 5 Signs He’s Never Going To Commit

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