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Embarrassing Questions to Ask a Guy

Embarrassing Questions to Ask a Guy and Make Him Feel Awkward

Are you looking for some awkward questions to ask a guy? If yes, you are at the right place, as this article will give you a list of questions that can cause a lot of embarrassment to any guy.
Deepa Kartha
Last Updated: Oct 06, 2017
Conversations are definitely the best way of knowing a person. Questions help us to get to know and understand people better. During the initial period of courtship, one needs to be careful about what one asks and tells. This is because you never know what may anger or embarrass the other person. However, once couples are comfortable with each other, they normally want to know more.
Although some of these relationship questions can cause a lot of embarrassment, it is sometimes very important in a relationship. So, if you want to know what your boyfriend really thinks about the relationship, here are the most awkward questions to ask a guy.
List of Questions
It is usually believed that girls become really touchy, when asked about certain sensitive topics, while guys are really cool about discussing anything. However, this is not always true, rather, even guys can be sensitive about certain topics. So, be really careful while posing any of these questions.
  • Do you really love me?
  • Do you think we will end up getting married?
  • Have you ever been disloyal to any of your past girlfriends?
  • Do you like kids? How many kids do you want?
  • What is the best thing that you like about me?
  • Why did you break up with your ex-girlfriend?
  • Have you ever been caught for shoplifting?
  • Are you still friends with your ex-girlfriend?
  • At what age did make love the first time?
  • Did you ever have a one-night stand, when you were in a relationship?
  • Am I better looking than your ex-girlfriend?
  • Have you ever regretted an affair or a relationship?
  • Have you ever indulged in drinking and driving? (If yes) Have you ever been caught?
  • Have you ever said, 'I love you', without meaning it?
  • Do I look fat in this outfit?
  • Have you ever done something very embarrassing in public?
  • Would you be fine, if I ask you get a blood test done, before we get more involved?
  • If you are given two choices, to kiss a guy in this room or to walk with no clothes on a crowded street for an hour, what would you choose?
  • If another girl hits on you, when I am around, how will you handle the situation?
  • What would you do, if I tell you that I am pregnant?
  • Have you ever been attracted to a guy?
  • Have you ever been addicted to drugs?
  • Have you ever sent a naughty message that got you into trouble?
  • What would you do, if you find that I am cheating on you?
These are some of the simple as well as funny questions to ask a guy. As I said earlier, these should not be asked during your first date, lest you want to shoo him off.
However, asking these questions can help you in knowing your boyfriend or partner better. One thing you must remember is that his reaction to some of these questions will depend on his nature. If he is very shy, he is likely to get very embarrassed when confronted with some of these. So, be extremely careful, you don't want to end up hurting him!
Cheerful couple laughing while enjoying a day at a cafe.