20 Questions to Ask a Guy That Deepen His Desire For You.

20 Questions to Ask a Guy That Deepen His Desire For You

Whether you’re dating a guy, living with a guy, or are newly engaged, you have the same challenge ahead of you.

It’s time to anticipate your man’s needs.

No, this is not about becoming a submissive woman or a perfect Stepford Housewife, none of that stuff. I simply mean the reciprocity of any relationship. He provides something valuable to you and in return, he hopes you will fulfill certain needs that he has—or that he may not even know that he has.

I’m not talking about his sexual desires. Sure, sex is fun…it’s easy to figure out, it’s fantasy fulfillment. And yes, the more effort you put into creating real life fantasies, the better it can be.

But what I want to talk about now is an even deeper need that every man has and how meeting this need makes a man fall in love and makes him want to commit.

And that is to emotionally stimulate him. You can do this through the art of conversation.

This is what makes him want to marry. Want to live together, want to go exclusive. And the best way to make it happen is to ask DEEP QUESTIONS.

Yes, stimulating your man’s emotions (even more important than stimulating his intellect) intensifies the relationship, because you not only make him think but you make him feel.

I’m going to give you 20 questions to ask a man that will INSTANTLY make him feel something, think deeply, and just love talking to you. These questions will deepen his desire for your company and make him realize no one else stimulates his mind like YOU.


1. What is your happiest memory of all time?

A great line, one that forces him to think happy thoughts and reflect back on the best moments of his life. And now, he’s sharing it with you!


2. If you were super rich, what would be the first five things you do?

A question that appeals to his good moral character, since you challenge him to think about life—and beyond limitations. Challenge him ambition and get him thinking about his future.


3. If you could get rid of all your fears instantly, what would you do?

Another clever question, since this makes him share some of his fantasies and dreams that haven’t happened because of his inhibitions. A man wants to feel as if he can tell you anything.


4. What is the worst thing that happened to you that turned out to be a blessing in disguise?

Great opportunity to have him become “the teacher” and explain to you a coming of age moment where he learned something.


5. If you could send a message to the you of 20 years ago what would you say?

Excellent opportunity to hear about his regrets, dreams and unrealized ambitions – goals you can encourage him to try to reach again.


6. What makes you feel most alive?

Be sure to do this experience with him for positive associations.


7. What is your idea of a perfect day and night?

Great for studying what he actually expects when you start living together.


8. What are you like when you don’t get your way?

Most guys will answer these “flaw” questions proudly. It’s a good opportunity for you to study their difficult quirks.


9. How open-minded are you about life? What are you not open minded about?

Men who are open-minded tend to be easier to live with. Men set in their ways and beliefs, can be a bit more challenging. Figure out what his most important values are, and try not to push too hard at these.


10. When you feel distant from your partner what do you do?

A good way to let him know what you expect from him, intimacy-wise, when there are arguments.


11. How do you express love?

Great question and it challenges him to think deeper—gestures beyond the physical and monetary. Find out how he expresses passion in life.


12. If you were a time traveler, what year would you travel to?

Nice way to see the “ideal time period” your man thinks about, where he feels he fits in.


13. What was your favorite toy or video game when you were a kid?

Bond with him by sharing memories! A man recalling his childhood memories will feel vulnerable fast!


14. What’s your favorite book, movie, song or TV series?

Find out a little bit more about what’s on his mind and what topics he relates to. This can be very indicative of the way he sees the world, how he feels about life, and what he wants to accomplish.


15. What’s your darkest, most taboo fantasy ever?

Be sure to let him feel free to describe his most taboo fantasy. Even if you can’t give it to him exactly, he will feel a sense of relief from just being able to say it in front of you.


16. If you could do life over again what skill / career would you try for?

Good question that reveals his character, beyond what he does for a living. Sometimes a man’s hobby or charity work IS his passion, and not always his job.


17. If you could meet anyone throughout history, who would you choose and why?

Who does he admire? Who does he strive to be like?


18. What’s the worst job you’ve ever had? Or, what’s the funniest thing you’ve ever seen?

Great for sharing a laugh.


19. What life lesson do you want to teach other people? (Or hand down to your children)

Give him the chance to share his wisdom.


20. What was your favorite family vacation?

Nice way to get him to talk about his family—and get used to the idea of introducing you to each one!


These 20 questions are great conversation starters. A man’s real NEED from a partner is that he is emotionally stimulated.

He wants to feel something and open-ended questions like these help him get in touch with his feelings and associate you as a friend who he can talk to about anything.

That’s where you want to be, because he will fall in love with you when he realizes you know so much about him and he’s always comfortable in your presence.


To the woman who won’t settle for “good enough” love…

Sometimes, real life is even better than a fairy tale…

I learned that while walking the empty streets of Prague.

(For the rest of this story, you can simply read this page: Click here)

Here’s how I remember it:

“Imagine you walk the streets of Prague, on a snowy December night. The cobble-stone streets click below your shoes… every corner looks like a painting from a museum back home…

You can feel the history in the air, and the romance wraps around you like an old coat.

Now, imagine you bump into a charming older couple. And you chat with them.

Their love is so clear, you ask how long they’ve been married.

“Sixty years,” says the husband, with a warm smile. He puts his hand on his wife’s back, and looks at her with love in his eyes.

“Sixty blissful years with the love of my life.”

You finish talking, but before you say goodbye, the woman takes you aside. And she slips an antique bottle into your hand.

“Take this,” she says. “This is my ‘true love’ secret to keeping my husband obsessed with me, for all these years.” “

Can you guess what her secret was?

I think you’d be wrong.

That’s why I continue the story on the following page:

Click here to learn more

29 thoughts on “20 Questions to Ask a Guy That Deepen His Desire For You”

  1. Sally Broessel

    Matt, Can a man ever be sorry he told you about a fantasy? He told me about a lived out fantasy once. (sexual) and I told him he was kind of scaring me. So then, he told me it was 15 years ago.

    1. Yes, I think he can be sorry he told you since your reaction was negative. I think he should also be able to talk to you about his feelings and if his lived out fantasy is something he wishes for the future. He might feel that the lived out fantasy was not something he wished for after all and he wishes not to repeat it. Honest open communication is key to discovering if this man is someone that fits your life and your future.

  2. The man I’m in love with is great in actions and deeds to show his love like breakfast in bed, doing extra chores around the house to free up my time, etc. but I long for more physical affection. I’ve verbally expressed this to him but me being vocal about my needs seems to keep him farther away. It’s like he thinks I’m scoulding him for not touching me more. I try not to make him feel this way but I’m a pretty blunt person. No need tip toeing and talking around something. Say what you mean and mean what you say. So is there anything I can do to make him more comfortable with random physical contacts? Like a kiss on the back of the neck when I’m doing dishes or just putting his arm around me when we are standing in line at the movies or something. I always always am the one touching him, and initiating sex. As a matter of fact, if I didn’t initiate sex, we’d never have sex! I want to feel wanted and desired. What can I do?

    1. Perhaps you both have different Love languages- yours is touch and his is acts of service.
      Look into these love languages and discuss them with each other – how you respond to your own love language and what your needs are. It is possible that you may need to do some acts of service for your partner for him to feel loved and he then understands that you need more touch.

    2. Along with having different love languages like Matt said, it sounds like you’re not expressing your needs correctly. You are being blunt and just asking or telling your man what he is doing wrong, and that’s not going to go over well because he doesn’t want to feel like he’s failing at making you happy/at the relationship. Instead, positively reinforce what and when he does do right (“I love when you kiss me like that!” “It makes me feel so happy and treasured when you give me these forehead kisses!” “Where did you learn how to do that sexual move you did the other night?! It knocked my socks off and made me feel like an amazing woman!”). You can also model for him by giving him random kisses, giving him a random massage, putting on something sexy but without asking for sex, etc.

    3. I agree with the others, perhaps your love languages are different, and perhaps if you did more”breakfast in bed type things, like he does for you, he’d start showing you more physical attention. I hope it works for you! Good luck!

    4. Shannon,

      I am sorry to say but how can this last if you do not feel desired by your partner? I have been there and after 11 years of the same and a lot lot of hurt I am out. In my case he had deep deep issues about his sexuality that only a therapist could fix(but he never went). I am sorry but it only gets worse with time if it is already like this. No amount you can do to change that. No amount of meeting his “needs” nor love language etc

  3. Daniella philbin

    I’m in love with a guy who lives miles upon miles away. We are dueach to get engaged soon. Then hopefully marry at some point next week or the beginning of 2022 around my birthday.
    I love him dearly & I know he lowes me too. I have never felt this way about any man ever in my life. It’s just heart breaking that we can’t be together right.

  4. Am in love with this guy who I met on Facebook. We have been talking for years now, he lives in America and I in Africa. But his origin is from Africa, the same country am living . Whenever he sets a date to come to Africa, something comes up and he won’t make it. We have never seen each other yet, we only do video calls. He talks to me all the time, he cares for me even though he has not meet me in person , he introduced me to few of his relatives here in Africa. He tells me everything, he even tells me about his female friends with benefits. But I have been stressing out about his coming to see me. He makes me feel special, he calls me his woman, but he told not to put my life on hold because of him, if I see a man that wants to marry me let me dont turn the man down. Yet he talks to me on the phone all day long while working or even at home when he off from work. He told me that when ever he is having sex with his female friends, he thinks about me, he feels as if he is cheating on me. He is really into me and yet he has not come to see me. Am so confuse, what should I do? He said he never tell me when he is coming, he will just surprise me.

    1. Someone who cares

      I am going to be brutally honest but your relationship does not sound like a healthy one. You can find someone that wants to marry you that does not fill his time with other women. If you were his priority, he would come see you. Lastly, I hope that he is not asking for or receiving money from you. If that is the case, it is a scam and you need to face reality and end it immediately.

      1. I was going to say the same thing… It sounds like a unhealthy and one sided relationship. If you are giving him money these are classic romance scams. Be careful!! also don’t send pictures. Good luck

  5. Well my name is Brenda Thompson. I met this man social media. He told me I was his heart desire. We started talking get to know one another and what we like in life. He works out of the country. He is a widow and he is raising his daughter by him self with her nanny. Well sense the covid-19 I haven’t been working in. I’m trying to open up my own business. So he wanted me to help pay his daughter hospital bill and he will give it back to me. When he gets back home. I told him I didn’t have any money right now. He kept on wanted me to help pay her bill. I told him I would try my best to help him. He telling me how much he loves me and what we do in the future together.. I couldn’t met the dead line for his daughter. He got so angry with me and he block me. I tried all my best to help with his daughter but it wasn’t good enough for him.

    1. Definitely a scam. If a man ever asks for money, please do not give it. I hear that story a lot, of a man being widowed raising a child. He works out of the country. I stop all communication. Good luck to you and be careful.

    2. It is a scam and I have heard from this contact. Block him and read Matt’s guidelines on on line dating it will save you heart ache and money. Been there done that, a piece of advise from someone who has traveled down that road.

    3. It is a scam…. I wish women would understand that these so called men that hide behind screens and tell you they love you etc…
      Please, know your worth. Please know that a REAL man would make a effort to see you no matter what is in the way IF they are sincere.
      Please do not waste your time. These are a dime a dozen !

  6. Hey Matt
    I have bf been dating for 2 years now everything is good in some parts like sex I dnt know what to do in that part we were doing great but not his sex drives does last long when having it and he want to pleasure me much as possible don t get me wrong the relationship is going really good it fantastic ………. it the sex part he having problem with

  7. I have known my man for almost 5 years and over time we have had too many breaks, and I feel I’m out of options to get him to commit and feel like he wants to be around. I feel like I’m the one pushing him away when all I keep trying to do is give him what he says he wants…. I really wish I could connect with the actual few word phrases that makes him come back and feel like I’m the only one and that he wants to be together instead of saying he needs or wants to be alone. Something I can say when all hope feels lost. I know he likes me or at least I’m pretty sure and I am so in love with him. Please help me Mr. Coast I watch so many of your videos and still never seem to catch just what i might need to do.

  8. My guys emotional needs are met by his female best friend who he used to be in an 8 year relationship with that ended 5 years ago. Why am I here. It’s way too much work for him to detach from that and I’m exhausted trying to prove myself.

  9. I’m 63 n my man is 66, every once in a while he ghost me for a while (2eeeks) no calls, no texting. We’ve been together for 8 months, in the beginning of course he told me that he wants to live with me and spend our lives together. Don’t know where that went what do you think?

  10. Elizabeth Simtustus

    Hi, Matt, this guy and I have been friends for years and then we got together one weekend , like 11 years ago and that’s all it’s been is weekends hook up and I’ve told him I wanted more, more than this, then he disappear for days, weeks then when I’m about to let him go he instantly messaged me and wants to come over or i go to him and I’m wanting more but he doesn’t and I know now, I’m only hurting myself by staying with him, or am I the one doing something else wrong here???

    1. You are hurting yourself by hoping something will come of this…. Believe me it won’t.. I’ve been there. Happened multiple times. In the end I had to give up completely. Blocked him and got on with my life.

  11. I’m in love after three months with a kind, Christian, good looking successful man that continues to send me morning quotes about life each day as his communication. He stays on the phone in his demanding busy job and therefore, hates to talk on the phone Since July I have talked to him three times in the phone. When I ask him to give me a quick call, he texts as if I didn’t ask. He says things like what a beautiful amazing mom and woman I am. Am I just too old fashioned? Even after having an amazing intimate night, he texted the next day a GN❤️. I know he is still sexually attracted to me and he shares things about snd pictures of his family. I’m so confused.

  12. I appreciate your article about 20 questions to ask your man. I have a hard time trying to start a conversation. And keeping it flowing and interesting. I have deep thoughts and answers. It’s getting them to come out in any articulate way. I feel like he finds me boring. And I am not boring. I got flustered easily. I will put your questions to the test. Keep you posted on the results. Fingers crossed. Ty, Kari

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