205. Being able to ask your guy some dirty questions encourages open dialogue within your relationship. What's the weirdest place you've ever done it? There are conversation ruts and you shouldnt overthink when they happen. Whether it be school debates, negotiating a longer night out with your mom and whatever else. How would you help me relax? Such inquiries may end up spelling disaster if you ask them too soon. Is it true that the lips of a stranger have the taste of excitement? What would you like me to say to you while we do it? What is the dirtiest thought about me that you have ever had? Note that dirty questions to ask a guy are a weapon for later dates! Heres how to show him your fun side and gain his affection. You might be surprised at some of the answers, so be prepared to not always hear the answer that you are expecting. How did you live it up? Would you rather see me in lingerie or nothing at all? Pick your questions carefully. 195. Whats the tastiest fish youve ever tried? Really, many of the questions just need a wording adjustment to apply to whatever the scenario is. By knowing his upbringing and other details, you will know in which way the conversation will go. What's one thing you want me to do to you that I haven't done? Our nervousness comes from the fear of failure. What would you bring to a desert island, if you could only bring three things? Do you check me out when I walk away from you? You might even feel like giddy teenagers who have just started dating for the first time. 105. These naughty questions can help encourage the two of you to explore your relationship together. Which one do you like? 65. Belief systems, social issues, and concepts are all in play here. The next date? What do you think I should wear to bed? What place on my body do you think is the most sensitive? These are just some of the dirty questions that you can ask a guy. What would you do if I sent you a dirty photo of me? 7. Relax! What world leader would you sit down and have tea with? 126. That sensitivity comes from the fact that male emotions arent looked at so normally in society. 225. 48. What is the longest intimate session that you have had? Treading into the unknown. Thats perfectly fine! How many people have you slept with? When do you think euthanasia will be legal? I heard that kissing can burn a lot of calories. 67. These funny questions to ask a guy are actually really useful. Relationships are not artificial; they are a living, breathing entity. If you could throw up on one person, who would it be? 177. How long could you live without it? What would your mom say about you right now? Its all about being fun, but with a seductive note. What would they think if they heard you? By seeing that both of you have awkward moments, you will feel closer and more human with each other. Its high time you put those sexy forearms to use? What's the wildest thing you've ever done? What was the worst situation you were ever naked in? Kassidi Christian krchris on April 11, 2019: These were brilliant questions. Speaking to the guy you adore can be a daunting task. How do I compare to other girls you've been with? How about a month? These funny questions to ask a guy will get him to open up. Awkwardness later, however, is a whole different story. What do you think about dirty talk over the phone or Facetime? Would you watch one with me? You will share funny stories, remarks and enjoy your collective sense of humor.