These questions are designed to make his easy going side shine through. They are more indirect and allow him to contemplate where he sees things going with you. Are there things you are superstitious about? What color is a chameleon on a plaid shirt? What is more important to you? What would be the one meal you could eat every single day and never get bored? People always say that the future is uncertain then why do we take insurance policies and go for career counseling? If you won a trip to go anywhere on earth, where would you take me? Do you prefer candlelit dinners at home or a fancy restaurant setting? Why do they call the airport a terminal if flying is supposed to be safe? Would a fly without wings be called a walk? What do you feel are your weaknesses?
It shows your smart side. What is your current goal at the moment? What was your worst job and why? If you had to choose an athlete to practice with, who would it be? What color is a chameleon on a plaid shirt? Do you prefer candlelit dinners at home or a fancy restaurant setting? These are still questions to warm him up. What are you earliest memories? What would you say to your President if you ran into him randomly? What is your favorite thing to wear to bed? Would a fly without wings be called a walk? What is your ideal romantic night? Can you think of a movie title that best explains your life currently? Why is a boxing ring square? To ensure that the date goes well, it is essential that you act as normal as possible and feel confident in front of the girl. Do you lead your life with your heart or your head? These questions are designed to make his easy going side shine through. What is your quirky pet peeve? Can you remember the funniest thing you ever did or said? What do you think people would say about you? What happened to the other 56 varieties of Heinz 57? If money was no object, where would you live? What do you feel is the sexiest part about yourself? What would your preferred super power be? Asking these questions will not only give you a gateway to his mind. One way to ease the tension is to use fun questions as an ice-breaker. Have you ever been caught in your birthday suit accidentally?
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