You have just noticed that cute tall guy, wearing black spectacles around the corner. His brooding eyes and muscular body has left you wanting for his touch on your body. But you have no clue about what to talk about or how to begin the flirty conversation over text that would not end like the usual small talk.

I am sure most of you have felt this kick in your gut a lot of times. To not be able to start a long-lasting conversation really frustrates you.

So, what’s the secret to a long conversation in a way so that he also knows you are interested in him?

The way is to ask the right questions.

Asking the right questions can make or break a deal. And if the questions are merged with the right pinch of flirting… Then it’s only time… when he will be yours.

Whether he is your neighbor you can’t help crushing on or the boy you have just met at the activity classes… The questions you are going to read will drive him crazy.

I can already see his footsteps leaving your home after an awesome night he has spent with you! 😉

So, what are you waiting for?

Read these questions and start asking them right away. Flirt with ease and leave the guy impressed.

Bold “Truth or Dare” questions to flirt with a guy

Truth or Dare questions are the best as it is not only fun but also revealing. The questions are so compelling that it leaves him with no choice but to answer. If you are at a party or a friend’s place and this game is being played, then use the timing to your advantage.

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Don’t lose your chance by asking him trivial questions. Instead, ask him these questions and trigger his interest in you!

1. What will you do if I remove all my clothes now?

Asking this question will make his feelings and hormones burst like burning lava. If he is bold enough, then his reply is going to blow your mind. Even if he tries to hide it, he can’t resist making a move soon.

2. Have you ever fantasized about kissing your favorite celebrity?

Everyone has a celebrity crush and people have thought things that they can’t convey in public. But in a game, he will end up telling it. It can also work as an icebreaker and make the environment sexy!

3. Is there anyone in the party you want to spend a night with?

This question can leave his cheeks red with a sly smile on his face. Of course, he has his eyes on someone with whom he wants to spend his upcoming weekend. But if you ask this question, chances are that at the end of the party he will stick around just so that he can ask you for your number.

4. Have you ever made an animal’s noise while having sex?

This question represents the naughty side of you and by answering it, he will prove how naughty and bold he can be during making out. And girl, if you are lucky enough, you will hear this sound soon. 😉

5. Have you ever had sex on a beach?

A little adventure hurts on one. And if the adventure revolves around sex… it can be a pretty wild one. The guy is a catch if he answers ‘yes’ to this question. If not, then maybe you can make his dream come true.

6. What animal you would like to play while having sex?

7. What is the first thing you notice in a woman?

8. Have you ever watched porn with a girl?

9. Have you ever fallen in love with your friend with benefits?

10. What are your two favorite sex positions?

11. Have you ever had a sex conversation with a woman while attending a funeral?

12. What is love to you?

13. If I was a genie for a day, what are the things you would ask me to do for you?

14. It’s been how long since you had sex?

15. What was your age when you first fell in love?

16. How many girls have seen your bare body?

17. If you were a woman for a day, what would be the first thing you do?

18. On a scale of 10, how much do girls rate you in bed?

19. Which body part do you like the most in your body?

20. What turns you on?

21. What is the most embarrassing moment of your life?

22. What was the last time you watched a blue film?

23. What are the five qualities you look for in your future girlfriend?

24. When in parent’s home, where do you hide your porn movies?

25. What is your most embarrassing sex story that you have refused to tell anyone?

Questions to ask on text to flirt with a guy

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You met a guy and was instantly bowled over by his looks. You exchanged numbers but never really had the kind of conversation you wanted.

But you can still smell his perfume and how he moved his eyes… It’s time to take things to the next level. And there is nothing better than text messaging to serve this purpose. Not only that it is personal but you also have the freedom to choose the perfect timing. (Always remember, if you wanna flirt, you wanna do it at night)

26. What will you do if you find me sleeping next to you right now?

Imagine sending this text to his number late at night. His reaction will be priceless. The question will trigger all the images of sleeping right next to you in front of his eyes and he will imagine all the things he can do to you.

27. Let’s play a guessing game. Guess if I’m wearing any clothes or not.

A woman’s naked body is the most beautiful pastel that a man desires. It’s a flirty question that will confirm your interest in him. He will love it and reply with the most sensuous talks you can ever imagine.

28. Don’t you think the weather and time is pleasant enough to fall in love?

Okay, this one is a bit cheesy. But he should know you are not here just for sexting and wasting his time. You have thoughts that go far away from just that.

29. How will you describe me with an emoticon?

What is texting (or sexting) without emoticons? A variety of emoticons allow users to select and replicate their exact emotions. Ask him this question and wait for what he sends you. It will explain what he thinks of you in a very short space.

30. What is the first thing you will do if I’ll cross your path?

Texting is fun and unexpectedly great! But it can never replace the joy of flirting in real life. Yes, texting can be used to fix a meeting and continue the flirt with the person sitting next to you. He can fix a meeting as an answer to this question and make future plans.

31. Which song reminds you of me?

32. How would you feel if I asked you to come to my place?

33. What do you feel when I text you… calm or horny?

34. If I send you a sexy selfie.. Will you try to defeat my sexiness by sending a sexier picture of yours?

35. If I appear in your dream after this conversation, what will you do to me?

36. Do you want to be hugged or kissed the next time we see each other?

37. How frequently do you find a partner for sexting?

38. When will I get the chance to sit in your charming presence?

39. Wanna workout together with me as your dumble?

40. How is it that every time I see your text a smile appears on my face?

41. Don’t you think the girl you are texting right now has all the potential to be your date?

42. If I’ll offer you raw coffee, will you make a drink or ask me to rub it against your chest?

43. Do you get turned on when you watch a sexy girl on your phone?

44. May I know how I’ll get a chance to dance with such a hot guy?

45. Morning or night… which time do you prefer to just do it?

46. Have you ever imagined doing dirty things to me? What was it?

47. Have you ever been attracted to the same sex?

48. Do you like it when I talk naughty to you?

49. Where do you touch yourself when I text you?

50. What is the naughtiest thing you’ve ever done to a date you got from dating sites?

Funny questions to ask a guy that will make him mad for you

Boys love humor. They never fail to make you laugh with their stupid tricks and jokes. A smile on your face gives them assurance. But they also love it when a girl shows off her fun side and makes him laugh.

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It lightens his mood and he finds you more irresistible than you have ever imagined. Being funny and asking silly questions will remove all thoughts of awkwardness and he will like you a bit more with every joke you make.

51. Do you want to be called ‘baby’ or ‘daddy’?

He may like being called both at different parts of a day. Be sure to see a smile or grin on his face when you ask this question. If he has got no one to call him both, then he can make you his sugar baby. 😜

52. What hormonal changes will take place if you see your male boss naked?

This is hilarious. It is very rare that men like his boss. Most of them hate their bosses for the extra work they give them. Imagining his boss naked can make him go ROFL and at the same time, he can go “ewww” and run for a glass of water.

53. Would you like to act like a tortoise on the bed?

Don’t overthink and waste your time properly using the Internet if you haven’t imagined a tortoise on the bed. The question can tickle his funny bones as well as make him horny. Don’t be surprised if he wants to be your tortoise.

54. If you find yourself locked with me in a room, how do you think you’re gonna resist my boundless cosmic charm?

Loving yourself is the best thing, right? But exaggerating it is funny. And he will know that you intend to make him laugh. You can also receive compliments for your cute little funny flirt.

55. What is your signature sex move?

Everyone has their favorite dance moves. So why can’t he have his favorite sex move? To make things sexier, you can ask him to go in detail and if all goes well, hit the chord and ask when can you both try it together!

56. Have you ever stripped for a Men’s club?

57. You will come dressed in which superhero’s attire when I’ll shout for you to come fast?

58. Have you ever farted on a date and got caught?

59. Have you ever come out of the office washroom without wearing your pants?

60. Are you gonna offer me the part of the protagonist if you release a music album someday?

61. Which of your aunts did you want to marry when you were innocent and a kid?

62. Have you ever forgotten to carry a mouth-freshener and ended up using body deodorant for your breath before kissing?

63. Would you like to trip over your Ex’s gown and as a result tear it down?

64. Who is the most beautiful woman who has rejected you?

65. What will you do if you forget to bring cash or credit cards on a date night?

66. Don’t you think you should not be a follower but a leader in case of asking someone out?

67. Have you ever sent a nude to the wrong person?

68. Why does the cute emoticon with its tongue out always remind me of you?

69. Which rule you will make if everyone follows you for one day?

70. What is the dumbest thing you’ve ever done other than not dating me?

71. If a female zombie hits on you, will you accept her proposal and have some action on the bed or you will run for your life?

72. What is the most hilarious dating memory of yours?

73. What will you do if you have just one condom for the rest of your life?

74. If you get a chance to be a woman’s body part for one year, which one will you choose to change into?

75. Would you hook up with aliens if you land up on the Moon?

On point “Would you rather” questions to flirt with a guy

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Would you rather is a fun flirty game and is very frequent in parties. Even if you are spending some good personal time with him, asking him these fun questions will be a great idea. Just add two options with would you rather and you are done. Here are some flirty examples that you can keep in handy.

76. Would you rather like to be by my side or on top of me?

This will make him think about holding your hand at one moment and then being on top of you in the other.

77. Would you rather take your date to a club or take her to your house for a pillow fight?

You never know when having drinks in a club can turn into a makeout in a car and pillow fights at his home can turn into action beneath the sheets.

78. Would you rather kiss your girl’s hand on the first date or kiss her lips at the first meeting?

Kissing hands is so romantic. But kissing her lips is both romantic and sensuous. What will he choose? Let’s see!

79. Would you rather cuddle on the coldest night of winter or have rough sex on the coldest night of winter?

Does he like cuddling or having rough sex? Or both of them? This question is flirty and sensuous as hell!

80. Would you rather smell your perfume or smell my panties?

Umm… You know the answer, of course. It will be your underwear. The next thing you can see is him struggling to arrange a private date for you.

81. Would you rather play it safe or play it loud?

82. Would you rather go jogging or kiss me to burn calories?

83. Would you rather make love on the terrace or make love on a Merry-go-round?

84. Would you rather talk naughty over chat or do it on FaceTime?

85. Would you rather strip dance or let me undress you?

86. Would you rather kiss my lips or get back with your Ex?

87. Would you rather want me in lingerie or without pants?

88. Would you rather take me on a brunch or cook for me?

89. Would you rather see “The Fault in Our Stars” or “Fifty Shades Darker” on our date night?

90. Would you rather eat chocolate or bananas if I feed you from my mouth?

91. Would you rather touch me from the front or you will hug me from the back?

92. Would you rather sleep with me for three nights or have a threesome?

93. Would you rather dance with me on a country song or shake it off on some pop?

94. Would you rather feed me a flavored ice-cream or gift me a flavored condom?

95. Would you rather live alone or with a beautiful partner?

96. Would you rather tell your friend the least favorite thing about him or smash his head on the wall?

97. Would you rather check out a girl without her knowing it or hold by her waist and let her know?

98. On a rainy day, would you rather watch classics or Netflix and chill?

99. Would you rather kiss under the water or make out under the water?

100. Would you rather have more money or more girlfriends?

101. Would you rather buy me a drink at the pub or buy me champagne in a hotel room?

102. Would you rather like to see me in a red dress or see me without a dress?

103. Would you rather do it just for a minute and call it a night or do it for the whole night till the sun shines?

104. Would you rather say sorry or kiss to end an ongoing fight?

105. Would you rather die peacefully in sleep or get murdered by your favorite porn star?

Questions that are intimate and flirty

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Knowing each other is very crucial whether you are in a serious relationship or just flirting. Intimacy is not just about the number of times he has had sex. It has much more to do with his conscience. How he thinks and what are his views on different areas of life, especially what he thinks about you and women. Here are a few questions you can ask to know your guy better.

106. Which part of the body would you like to get touched the most?

This question will trigger deep feelings and make him horny. Also, knowing his weak points can be very beneficial for you if you want him to crave for you.

107. What do you think of women in lingerie?

Watching a woman in lingerie makes the most beautiful image for a man. A woman in lingerie with its soft fabric and sensual colors makes him weak and want you more. You should totally know about his views on this.

108. Are you into soft sex or BDSM?

If you are looking forward to spending some time with that guy, then it’s necessary for you to know about his choices – especially, his sex choices.

109. What is your wildest sexual desire?

His desires are essential to you if you are thinking of dating or marriage. After all, this question will help you know what’s in it for you in your sexual future! 😉

110. Do you intend to care for your girl during her periods?

If the guy cares for you and women or is just playing around with you will be answered by this question. It will determine what he thinks of women- just as a sexual being or a living creature who has emotions.

111. What were the last two movies that you watched with a girl?

112. Are you desperate to get me or I’m just one of your chicks?

113. What lesson have you learned from your past relationships?

114. Was falling in love your best mistake or worst mistake?

115. Do I remind you of any of your crushes?

116. What would you do if I sat on your lap without any clothes?

117. Do you look forward to getting old together with your partner?

118. What is the thing that you always wanted to say but never got a chance?

119. Where would you want me to kiss you?

120. Do you like hickies?

121. What are your thoughts on adopting pets with your partner?

122. What is the manliest thing you can do for a woman?

123. How do you describe me to other people?

124. What do you think of women who propose to you first?

125. What do you miss the most about me?

Now that you know all the flirty questions that can make things go miles further and make you feel a lot of emotions, it’s time to give them a try!



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