82 Very Best Questions to Ask A Guy

82 Very Best Questions to Ask A Guy

Let’s just say it…

Guys are not like girls…not usually.

They think different. They act differently. They do things that make no sense.

Everyone knows that effective communication is the key to a healthy relationship.

It would be nice if you could just ask a question and get a simple answer.

It’s not that simple….

Men think differently than Women, you need to be insightful about your questions and clever about how you ask them.

I’m here to assist.

50 questions to ask a guy. I broke things down into 5 different stages of a relationship. We’ll cover:

General Questions
The First Date
The Trial Period
The Honey Moon Phase
Seriously Dating
Together for Years.

Let’s get to it!


General Questions

Questions to ask a guy

1. What are your personal goals?
2. What kind of childhood did you have?
3. What makes you insecure?
4. What do you expect from a love relationship?
5. What’s the one thing you can’t tolerate?
6. What do you find attractive in a woman?
7. What expectations do you have of yourself?
8. What was your most memorable birthday?
9. Have you ever worn girls clothing?
10. Who are your family and friends?
11. What kind of music do you like and which places in the city do you like to go to?
12. What’s the one thing you can’t live without?
13. What is your funniest memory of high school?
14. How do you feel working for (company)?
15. What’s one item you’ve recently crossed off your bucket list?
16. If you could describe yourself with one word, which would it be?
17. What is your favorite food?
18. What is your favorite character from childhood?
19. What kind of animal do you love the most?
20. Would you rather choose fishing or hiking?
21. Do you believe in God?

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First date

Questions to ask a guy

Questions to Ask A Guy

Around the World, Men and Women alike bubble with excited nervousness at the thought of the 1st date.

You’re intelligent and compassionate with a wicked sense of humor…  

He just needs to get to know you….

Expecting someone to fully get to know you after just 1 date is an unrealistic expectation.

All hope is not lost.

You can show your great qualities without coming off as try hard

Leaving him intrigued and curious about you…

By randomly tossing these questions into the conversation…

  1. What’s the number one thing that you don’t like about Women?
  2. Do you think that dating is harder or easier with the internet?
  3. Are you intimidated by Women that make more money than you?
  4. Who was your celebrity crush when you were a young child?
  5. Do I make you nervous?
  6. How do you feel around me?
  7. Do you ever lie to get what you want from girls?
  8. What was the first thing that came to your mind the first time you saw me?
  9. Would you rather win 1 million dollars or fall in love?
  10. Do you have any questions for me?
  11. What is your romance spirit animal?

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The Trial Period

Questions to ask a guy

Questions to ask a guy

Things are looking good. It’s obvious he likes you, and you like him.


The lack of certainty is causing anxiety…

You’ve found your perfect dance partner and…

The music can stop at any moment.

You don’t want it to stop….

Now is the time to move things forward.

Time to start asking the right questions to get some clarity on your relationship status.

Ask these questions and he’ll get the idea.

  1. Do your friends know about me?
  2. Do you want to date other girl’s or do you want to have me?
  3. I’m a lot to handle, are you sure you want to date me?
  4. Would you be jealous if you saw me flirting with another guy?
  5. Do you want to come to hang out with my friends?
  6. Do you mind if I post this picture of us on Instagram?
  7. Can you give me a massage?
  8. If I never talked to you again, how much would you miss me?
  9. What did you think about me on our first date?
  10. Are you surprised that we are still dating?

Bring in some laughter with these dad jokes.


The Honeymoon Phase:

Questions to ask a guy

Questions to ask a guy

You’re falling in love.

This is different. He might be the ‘One’. You think he might love you.

You’d like to know.  

Your friends are saying that you’re crazy in love. You don’t care what they think.

Time to figure out exactly how real this love it is.

Is this too good to be true? Or is this the real thing?

Ask these questions to get the answer.

Pay close attention to his responses and reactions…

  1. Do you like being with me?
  2. Does your Family know about me?
  3. If you could fly anywhere in the World with me, where would we go?
  4. Why did your last relationship not work out?
  5. Are you afraid that I will break your heart?
  6. Do you ever want to have kids? If so, how many?
  7. Would you rather live in a fancy condo in a major city, or at a ranch on a farm?
  8. Would you still want me if I get old and ugly?
  9. Have I ever done or said anything to upset you?
  10. Do you ever remember your dreams? What are they about?

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Seriously Dating:

Questions to ask a guy

Questions to ask a guy

You and your Man are official.

You know it. He knows it. Everyone knows it.

Things are serious. You don’t know exactly how serious.

Will he be the love of your life? Forever?

How can you know for sure?

He’s probably thinking the exact same thing…or is he?

Time to start asking questions that will reveal the truth…

Without scaring him away.

Casually toss these questions at him while you guys are sharing an intimate moment….

  1. Would you like to come over to my parents house for dinner?
  2. Do you have any deeply hidden secrets that you want to tell me?
  3. If we have children, and I love them more than you, can you handle that?
  4. Do you want to take a break from our relationship?
  5. If I moved to a different state for work or school, would you come with me?
  6. If we had to have a long-term relationship for 1 year, would you remain faithful?
  7. Do you understand that If you marry me, you are also marrying my Family?
  8. Would you rather travel the World with me, or with your guy friends?
  9. Are you okay with me having guy friends?
  10. If I were to marry you, what would you expect of me?

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Together for Years:

Questions to ask a guy

Questions to Ask A Guy

You guys have done it all. Been thru it all.

Here you are, still together.

Safe to say that neither one of you are going anywhere.

At this point, it just seems natural to assume things.

However, people do change as they grow.

This may be the most crucial stage to be asking important questions.

Asking him these questions will tell you what has changed, what has stayed the same…

And where the two of you are headed…Ask with care.

  1. Are you still satisfied with our relationship?
  2. Over the years, have you ever wanted to give up on our relationship?
  3. 10 years ago, what did you imagine that our lives would be like?
  4. Are you willing to make a change in career, even if it means a change in lifestyle?
  5. Have you ever thought about moving to another state or country?
  6. What is something that is still on your ‘bucket list’? Why haven’t you done it?
  7. If I get very sick, will you take care of me? Or send me away?
  8. Do you find me as attractive as I was when you first met me?
  9. Do you love me now for the same, or for different reasons as before?
  10. If my parents get very sick, will you help me take care of them?


Bonus / Random Questions to Ask a Guy:

What’s on your bucket list?
Which social media do you use the most often?
What kind of music do you like and which places in the city you like to go out?
If you could only eat one food for the rest of your life, what would you choose?
Which fictional character scares you the most and why?
What is your favorite movie of all-time?
What’s your dream job, where he would like to work, and do you have any ambitions for the future?
Do you believe in God? Do you have role models and idols, and who are they?
Is physical appearance the most important?
If you could live anywhere in the world, where would it be?
What is the happiest event of your life?


Remember. Everyone has questions.

Your questions matter, and you deserve to ask them.

As important as it is to ask YOUR questions, it is just as important to ask the RIGHT questions.

He has just as many questions as you. Keep an open communication line, and you’ll find that your relationships with Men will be much simple and better.

Happy asking.


Dating for Girls:

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How To Tell If A Guy Likes You Over Text
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50 Questions to Ask Your Boyfriend
75 Questions To Ask Before You Get Married
20 Things to Talk About with Your Partner
20 Questions Girls Are Afraid To Ask Guys