“I’ve been seeing this guy for a little while now and it seems like sometimes he’s interested and sometimes he’s not. I feel like I don’t really have him and I feel like I don’t know how to hold his interest and make him want me more.

I notice this the most when we’re texting. Sometimes he’s there texting back and forth with me, sometimes he disappears for hours or days or doesn’t really seem to engage in the conversation.

MORE: Exactly How to Get a Guy to Text You Back

There are all kinds of videos and articles about text messages that make him want you, but a lot of the advice seems unrealistic or ridiculous. Can you tell me what works to make a man interested over text?”

Creating a connection comes down to one important thing: questions.

And it seems in this digital age, the art of conversation has been lost and we don’t know how to ask the right questions to really get to know someone. And that’s what dating is … it’s a discovery process. And the best way to discover someone and to assess how compatible you are, is through asking the right questions.

There’s a time and place for the right questions … a time to keep it light and a time to go deep.

MORE: 225 Amazing Questions to Ask a Guy

This doesn’t mean you can’t ask serious questions when you’re first getting to know someone. There aren’t strict rules you have to follow because things like context and tone really matter. But you probably don’t want to pull out “When was the last time you cried?” on a first date (unless it somehow comes up naturally and you really get the vibe that he’s open to talking about it …)

Tone is key. Asking him “What is one thing you’re judgmental about?” can be either lighthearted or serious depending on the context, how it’s asked, and how he chooses to respond.

In this age of endless connection, we are more disconnected than ever and most relationships don’t go very far beyond the surface. Maybe it’s because we hold ourselves back or maybe it’s because we no longer have the tools to genuinely connect, like face-to-face and via conversation.

In order to build the foundation for a relationship, you need to create a meaningful connection, and this comes when you truly connect with who the other person is.

A little while back, I discovered this site called Thought Questions and I started keeping a list of some of my favorites. When my husband and I were still dating, I pulled up the list one night and suggested we play the “questions game.” We also mixed it up by seeing if we could guess what the other person would answer. It was a lot of fun, but also a very profound experience and we ended up learning so much about each other (and about ourselves!), which brought us even closer. To this day we make an effort to spend time asking each other deep, meaningful questions that go beyond ‘how was your day?’ And every time we do this, we discover new and interesting things about each other.

MORE: 225+ Amazing Questions to Ask a Guy

In his book “The Seven Principles of Making a Marriage Work,” famed relationship researcher John Gottman (the dude who can predict whether a couple will get divorced with something like 95% accuracy after watching them interact for only a few minutes) cites “enhancing your love maps” as the first principle. A love map is essentially knowing all relevant information about your partner’s life, from small things like the name of their first pet to big things like significant experiences that shaped who they are. He explains that couples who have detailed love maps of each other’s worlds are much more equipped to cope with stressful events and overcome conflict.

The point is, knowledge is power and asking the right questions can unlock the gates for a meaningful connection and deep understanding of one another. It doesn’t matter what stage of a relationship you’re in, it could be the first date or your 10th year of marriage, people are deep and complex and always evolving so there is always something new to learn.

To help you tap into the power of knowing, here is a list of my favorite bonding questions to ask your guy in order to get even closer and more connected.

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I know I am a woman of high value, worth and integrity. However, I tend to attract emotionally unavailable men and struggling what to do about this issue.

I have been told I am an alpha female and have toned down a bit since re-entering the dating scene. I think men are now attracted to me due to my recent career success, yet I think the right men are intimidated by me. Any insight?

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Breaking the ice with a guy you like can sometimes be challenging. It can also be tough to break past the typical flirty banter and really get to know each other.

I don’t know about you, but nothing is more painful to me (in a not physical pain sort of way) than awkward silences, especially on a date. And talking about the same old things can get tedious.

A little while back I started keeping a list of cool and interesting questions to ask a guy in an attempt to avoid awkward silences and generic conversation. Early on when I started dating my husband, we had a “questions” date night and it really brought us closer and helped us discover things about each other, and ourselves.

And this is something important to keep in mind about conversations in general.  Conversations aren’t meant to impress another person, but to discover them. Most people don’t take this approach and that’s why dating can feel so stressful and overwhelming. You can’t just be, instead you try to be what you think the other person wants. The best approach is to go in without an image of them, and without wanting to seem a certain way in their eyes. It’s to see them as a blank pice of paper and see how they fill in the blanks.

MORE: 20 Questions to Ask a Guy to Get Closer

And with that, here is my ultimate list of questions to ask a guy to bond, connect, and just have a laugh! Some are silly and lighthearted, others are deep and serious and will really force him to step out from behind the mask and share his true self… and that is what creates a connection and real intimacy.

I gave a little bit of explanation for the first 50 questions, just to show you why they are such good questions to ask and what they will reveal about a person. For the remainder, I just listed everything out.

All of these questions will open the gates to a deeper connection and bond, something so many people struggle with in this day and age. So enjoy the list, jot down your favorites, and have fun going through them with a guy you like.

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The Very Best List of Really Random Questions to Ask a Guy

A lot of people get stuck when it comes to face-t0-face conversations .., maybe it’s because it’s not what we’re used to and it just seems way more intimidating than talking through a screen.

MORE:225+ Amazing Questions to Ask a Guy

Asking the right questions can open the gates for deeper communication and help you really get to know the other person. We usually categorize our question articles but the following list is pretty random. These unconventional questions are pretty out of the box but can lead to interesting answers … which can lead to interesting conversations.

Try them out with a boyfriend, crush or a guy you’d like to be dating.

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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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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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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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So I’ve been seeing this guy for a few months now. At first, everything was amazing. We hit it off right away and during the first few weeks, he seemed super into me. He would text me things like, ‘I miss you’ and ‘Can’t wait to see you’ and on our second date he said he ‘never liked a girl so much after only two dates’. He was also super attentive and super sweet.

All this was great, but then he started to shift and lately has been acting really shady- he cancels on me last minute, he’s been acting distant, and I’m just getting weird vibes. At first, I thought he was just trying to end things, but then from time to time, he’ll text me something really sweet, like about how much he wants to see me, or that he’s been thinking about me, so obviously, he’s still interested or why would he do that?

Anyway, I’m really confused by his behavior, my friends say I should just forget him but I really feel like we could have something great and I’m not ready to throw in the towel just yet.

Am I deluding myself? Please help! Why are guys like this!?

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My boyfriend has become withdrawn lately. He’s really stressed with not working, his dog dying, best friend’s dad having lung cancer, and everything just adding up.

He’s been pulling away for a couple weeks and has recently started going a day or two without texting me.

Should I stop texting him all together, or will that be showing that I don’t care and that I’m not supportive? I want him to know I’m here for him and that I’m not going anywhere, even though it’s tough. What should I do? 

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Do you have any advice on how to tell if a guy loves you?

I’ve been seeing this guy for almost a year know and though he says he loves me, I just can’t tell if he’s just saying what I want to hear or if he really does love me.

He’s not the type of guy to gush with lots “romantic talk”, but it’s more than what he says that makes me worried… sometimes I feel like if I didn’t text him or set up dates, he’d disappear or forget I even existed at all.  Is it possible for a man to say he loves you and not actually be that into you?  How do you know if a guy loves you?

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“There’s a guy at work that I’ve been interested in for a while.  The problem is, he sends mixed signals and I can’t tell if he really is interested in me and flirting or if he’s just being friendly.

What do guys like in a girl?  What makes a guy want to date a girl versus not seeing her as “girlfriend material”?  What do men want in a woman that makes them see them as a catch?”

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My ex broke up with me last month after being together for over a year. The last few months were rough because his grandmother passed away after being in the hospital for a few months. I tried to be there for him but he totally withdrew and would reject my advances and we started fighting a lot because of it.

He told me he loves me, but felt like I was smothering him and he needed to find himself. I told him I would give him space while he figured things out but he said he couldn’t ask me to do that. I asked if there was a chance for us once he got things sorted and he said he isn’t sure if he sees a future. He said he worships the ground I walk on and should never change because I was perfect in the relationship and will go far in life whereas he feels like he has nothing to offer since he is grieving and stuck in a job he doesn’t like.

He suggested we stay friends but I told him that would be too hard on me and he said I can contact him anytime. I know I came across needy over the last couple of months and am wondering if there’s anything I can do to get him back. Should I text him? Try to stay friends? Is there any hope of getting him back?

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I’m at a place in my life where I want to find true love – not another fling, not another dead end relationship, not another man who just wants something casual.

How do you find love?  I want real love, the kind of love that lasts with a man who loves me for who I really am and wants to be with me forever.  Where can I find love and how do I know when I really have it?

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I’ve been with my boyfriend for four months and he’s been acting more and more jealous.  At first, I found it sweet, but this weekend he snooped through my phone and accused me of talking to other men.

I can tell you with complete honesty that I haven’t talked to any other guys… the thought doesn’t even cross my mind.  I kept telling my boyfriend that I’m only interested in him, but he seems cold and withdrawn now. It’s like I’m being punished for a crime I didn’t commit.

Is this normal jealousy or is this something beyond? Can you tell me what to do when a guy is jealous?

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I’ve been in my relationship for over 2 years. We started out great. He was attentive, sweet, caring and I felt on top of the world with him. However, looking back I can see that after 3 months, the relationship dynamic started to change and I started to change. He started to put me down, get cold emotionally or get really angry from time to time… It wasn’t over-the-top or out of the ordinary and I would just let it go since I just wanted the relationship to fall back into harmony.

Now, after 2 years into the relationship, I’m starting to question if I’m in a toxic relationship. I have felt for a long time that I have to walk on eggshells around him… I’m afraid to say or do the wrong thing around him because I never know what will trigger his anger or harsh criticism.

On the other hand, though, when things are good, they’re really good. Our sexual chemistry is amazing, I have never connected with a man the way I connect with him and when he’s happy with me I feel like I’m on top of the world. I still love him very much and despite the negative ways he acts sometimes, I believe he loves me very much too. He’s always been faithful to me, he pays all my bills and we live together now.

I feel so conflicted: Am I in a toxic relationship? Are toxic relationships repairable? Is what I’m experiencing normal in a relationship from time to time?

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I’d like to know specific things I can do to turn on a man.  I read your last article about the having the right mindset to seduce men, but I’d like to know what behaviors, tactics, and actions a woman can take to make a guy really turned on and hot to pursue me.

Can you talk about how to turn a guy on through specific actions?

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There’s a guy who I’m really interested in, but there are all sorts of women throwing themselves at him and I need to stand out from the crowd.

I am not unattractive, but I don’t feel like I’m necessarily the hottest woman in the room either… I think I can look good if I really put in the effort.  I don’t have trouble with guys in general, but I really want this particular guy and since there’s competition, I really want to know how to seduce a man and how to hook a man’s interest.  Can you tell me what works best?

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I’d like to know your rules for having a friends with benefits arrangement.  I’m not looking to be in a relationship right now, but I’m only human and I have needs.  I want something that’s dependable enough that I can take care of my needs without having to jump from guy to guy or pick some guy up at a bar or club.  Yes, I understand that this isn’t what women say they typically want, but I just got out of a long, difficult relationship and I don’t want to dive right back into commitment again.  

Can you tell me the best friends with benefits rules so I can make this happen without drama or complication?

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I have been seeing this guy for a little while now, it’s a long-distance relationship and we aren’t exclusive. When we’re together, he seems super into me.  He talks about me to his friends, engages in PDA, and compliments me all the time. He initiates every conversation, checks up on me if I don’t reply, makes plans in advance, clears his schedule for me, etc., and I know for a fact that he isn’t seeing or hooking up with anyone else. 

He tells me he misses me and that distance sucks because we can’t be together, but adds that we should keep our options open in the meantime. I tried ending it, but he begged me not to (although he also said he would understand if that’s what I truly wanted). In the end, we both decided to keep the lines of communication open.

I can’t wrap my head around the fact that he says he genuinely likes me but still wants to play the field when I’m not around and doesn’t mind if another guy snatches me up. Is distance a legitimate reason not to commit, or is he just not that into me?

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I’ve been having some issues in my relationship and I’m wondering what is the best way to go about resolving them, instead of making things worse and getting into the same fights over and over.

One issue I’m currently dealing with is my boyfriend has me blocked from some of his social network activity. I discovered it recently and haven’t said anything yet but it’s really bothering me. Should this be raising red flags or am I just overreacting? And what is the best way to bring it up without pushing him away?

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I’m dating a guy that is really hard to understand. It’s like he’s determined to find reasons why things won’t work out, and yet I know he cares about me and doesn’t want to end it.

We are long distance right now so he has legitimate concerns, but what I want to know is this…when do you throw in the towel for a guy who is clearly putting up tons of walls and protecting himself from potential pain, and when do you keep putting up with somewhat ridiculous behavior knowing that once his walls are down, it could be a gold mine under all that fuss?

He’s been acting like a huge jerk lately and I really want to just tell him to get over himself, but I’ve seen very clearly how amazing and loving he is and truly think this is all just a form of protection “in case we don’t work out.”

I want to “crack his code,” but at what cost? Normally I wouldn’t ever put up with this kind of behavior, but something tells me to keep digging and to be patient. Am I wasting my time?

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I dated a guy for two months and everything seemed perfect until he told me that his last relationship was three months ago. That relationship was a year long, so when he started seeing me they had only been broken up a month. Once that was out in the open he started distancing himself and I eventually broke it off because I was over the inconsistency.

I typically don’t like bringing up the past. I feel like the past should be left alone. But after my last experience I think it’s an important thing to know so that I don’t put myself at risk and end up the rebound girl.

So when you should ask a guy when his last relationship/serious dating/fling was? And how can you do it without it coming off in a negative way?

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I wanted to ask for your take on guys who play games in relationships, like the texting game, for instance. I thought people stopped that after college, but recently found out I was wrong.

I hate the whole game of one person sending a text and the other waiting two hours before responding, even if they have their phone and aren’t busy, just so they don’t seem desperate. I really don’t like playing games but this guy I’m involved with is being very confusing and I can’t tell if it’s just a game or not.

Is there a way to break the texting game or is that who that person is by nature and there’s nothing that can be done? How can I beat the texting game?

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I know you talk a lot about how men love a happy woman, but I’m having a really hard time being happy with my relationship as is. I always feel like I need to figure out why my boyfriend is acting a certain way, and I can’t help but worry that he’ll leave me for someone else.

I also get really frustrated when he doesn’t do things I ask him to do, like basic chores and stuff. I don’t want to be needy or a nag, but things like that make me feel loved and cared for. I want to enjoy the relationship and bring happiness to it, but it’s hard for me to get there when I feel like he doesn’t care most of the time. I don’t want my relationship to be a constant struggle.

So my question is,  how can I fix my relationship and stop it from falling apart?
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Me and this guy started off as friends but thing quickly turned romantic between us. He was doing an exchange program at my university and after a few months moved back home, but we continued to stay in contact and visited each other several times. Over these last few months we don’t talk as frequently, but we do have occasional lengthy phone calls where we talk about everything.

I don’t know where I stand with him because we never discussed it, plus we are both not very expressive/overtly emotional people, and I never expected (and still don’t) a relationship to blossom from this, but I do have strong feelings for him and want to see him soon. We are both going to be in Vegas next month and he messaged me asking if I want to meet up. Maybe I’m just paranoid, but I feel like he just wants a guaranteed hookup.

I guess my question is, is it normal for an ex-fling whom you were once romantically and sexually involved with to always reach out and initiate long conversations? Is it just to be polite/friendly, does it mean he misses me and still has feelings for  or am I just his “fallback girl”?

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