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First Date Tips for Guys: The Best 105+ Questions to Ask Her

Updated on January 11, 2019
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Isaac is a dating coach/life coach and a freelance writer for hire.

First Date Tips for Guys

First date tips for guys
First date tips for guys | Source


A first date can feel scary. So many questions can arise in your mind and increase your levels of nervousness.

Can I engage the girl or woman well enough for her to wish to date me again?

Can I make a good impression on her?

Are we doing this just this once or will she give me another opportunity to entertain her?

What should we talk about?

Here are some first date tips for guys questions you can ask to make the woman enjoy the experience so that she will date you again.

  • Are you feeling nervous?
  • What do you think of this place?
  • Do you like to date in an upbeat atmosphere or in a cool place?
  • What came to your mind first when I approached you to ask you to date me?
  • How did you feel after I requested this date?
  • Why are you wearing the dress you have on?
  • Who do people say you are?
  • What is your reputation among guys? Do guys think you are a great lady or an unfriendly woman?
  • What do you think is the most ideal place to meet a life partner?
  • Why do you think some couples are happy?
  • Have you ever seen a waterfall before? How did you feel when you saw it?
  • Can you resist peer pressure?
  • What are the things you like about your brothers?
  • Which is your favorite flower?
  • Do you know any self-defense skills? Which one(s)?
  • Do you believe in working things out all by yourself when you fail at something, or you accept help from others?
  • What do you think of people from different cultures who don’t understand life the way you do?
  • Which is more important to you, listening or being listened to?
  • Are you suspicious of strangers?
  • What are 20 myths you’ve heard about relationships?
  • What misconceptions do you have about dating, guys, and love?
  • What was the first lesson you learnt about trusting men when you started feeling attracted to guys?
  • Have you ever been on a desert before?
  • What would you do if a guy tried to touch you or kiss you against your will?
  • How do you combat boredom?
  • How do you deal with change?
  • Which is more important to you, looking beautiful or acquiring knowledge?
  • To you, what is true masculinity? What is true femininity?
  • Can you accept discipline?
  • What gives you peace of mind?

  • What gives you fulfillment in a relationship?
  • Have you ever been in a goldmine before?
  • Do you judge by appearance? Have you misjudged a guy before?
  • Do you trust your first impressions of a guy?
  • Have you ever gone on treasure-hunting before?
  • Which is your favorite fabric?
  • Which teacher bores you the most in class? Why?
  • Who is your favorite co-worker? Why?
  • Have you ever been really desperate in life before? What caused the desperate situation?
  • How long did your longest face-to-face conversation with a guy take?
  • What do clothes mean to you?
  • What is your greatest need in a relationship?
  • Do you think the love of money is harmful?
  • To you, what is true riches?
  • Do you think it is wrong to date secretly?
  • What is your idea of a great weekend?
  • What type of dressing do you think makes a guy look great?
  • What do you know about cars?
  • Have you ever seen a woman and thought, “Wow! I wish I had that face, those breasts, hips, and her figure?”
  • What is the worst advice your girlfriends have ever given you?
  • Have you ever seen a woman and thought, “Wow! I wish I had that face, those breasts, hips, and her figure?”
  • What is the worst advice your girlfriends have ever given you?
  • What is the most important truth you have ever told to a guy?
  • What 10 new things have you learned about guys over the past week?
  • What about women do you think guys take for granted?
  • To you, what does being disrespected by a guy mean?
  • When was the last time you were broke?
  • To you, what is a terrible relationship?
  • Were you a cheerleader at school?
  • Who is your favorite romance writer? Why?
  • Who is your favorite dating coach? Why?
  • Do you think dating is more enjoyable than marriage?

  • How do you solve problems when they crop up?
  • Are you filled with fear at the end of every year, or are you filled with hope?
  • What question about life is the hardest for you to answer?
  • How do you think we can make our next date more enjoyable?
  • When was the last time you gave food to a homeless person?
  • Have you been rescued from danger by a guy before?
  • Has a brother or sister betrayed you before? What happened?
  • Do you like to control a relationship or you feel comfortable when the guy is in control?
  • Who is the most arrogant guy you have ever met?
  • Do you feel complete? Do you think getting married will complete you?
  • When was the last time you made a guy cry?
  • What would make you stand and applaud a guy in school?
  • Have you felt pity for any guy before? Why?
  • Do you assert your needs often?
  • What do you do to heal emotional pain?
  • What is the greatest miracle you’ve experienced in life?
  • Would you donate your kidney to your brother if he developed kidney problems and needed a kidney transplant?
  • How do you say goodbye to your girlfriends, with words or with a kiss?
  • What is your idea of an adventurous date?
  • Would you share a secret with a woman or a guy? Why?
  • Do you prefer to sit at the back of class or in front? Why?
  • What do you think of bald guys? Do you think they are sexy as some say?
  • Which do you prefer, a guy with black hair or a guy with red hair?
  • What is the size of your feet?
  • Do you like rabbits? Why?
  • Have you send a rabbit walking on its hind legs before?
  • What is the best wedding you’ve ever attended?

  • What do you think of man’s youthful days?
  • Do you think there is something worth imitating about me? What is it?
  • Do you believe in telepathy? Have you communicated with someone telepathically before?
  • Do you believe in numerology?
  • Do you know how to fire a gun?
  • Have you parachuted before?
  • Do you like wearing caps?
  • When was the last time you used a binoculars? What did you view with it?
  • Have you run in a marathon before?
  • Do you love improvizing when you don’t readily have what you need to do a job?
  • Do you like doing research about various aspects of life?
  • Do you love experimenting with different dating ideas?
  • Have you initiated a date before? Do you expect a guy to initiate a date always?
  • How do you handle dating anxiety?
  • To you, what is good dating communication?
  • Do you have any dating values?
  • What sort of behavior do you expect me to show whilst we date?
  • How often do you set new goals for your life?
  • Which do you prefer, doodling, speaking, or acting?
  • Have you had a very serious fight with a woman before? Who was it?
  • Do you love your neighborhood? Would you like to live there for the rest of your life?
  • What do you hate your neighborhood? Would you like to move away if you had the chance?

In Rounding Up

These are the first date tips for guys that I have for you. Step out with confidence in your heart, relax, be yourself, and release the questions gradually and the lady will enjoy the experience and probably commit to a long-term relationship.

© 2018 Isaac Yaw Asiedu Nunoofio


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    • Papeeebooks profile imageAUTHOR

      Isaac Yaw Asiedu Nunoofio 

      11 months ago from Ghana

      Thank you for your comment.

    • BlossomSB profile image

      Bronwen Scott-Branagan 

      11 months ago from Victoria, Australia

      An interesting article and you have some good points here, especially about the way the girl presents herself. However, it cuts the other way, too: if the guy does not meet her expectations, she is not likely to react in the ways that he hopes she will. If he only speaks about his own interests and does not listen to hers, or his jokes are not to her taste, it will be a real turn-off and there may not be another date.


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