Just be sure to choose a game you're sure to win or tie, or you may find yourself doing all the talking. If your guy is competitive, he may be more willing to participate if you make it a game with rules and points. As mentioned above, write the questions on slips of paper and put them in a jar or bowl. Select a question and ask it; if he answers, he gets a point. If he decides to pass on the question, he doesn't get the point and you get to ask another question before it's his turn.
He'll have a bowl full of questions for you too, so take turns in asking and answering questions. The best way to win is to answer all the questions, and the quickest way to lose is to pass on answering, so it's to his benefit if he answers all the questions the first time. The first person to 21 points wins. Unless you've both decided to have a formal session of getting to know each other by asking any questions that have been on your mind, keep things low-key. Let the questions follow each other naturally as the conversation unfolds.
Ask one of the lighter questions and follow that path until you get to a point where you can ask more serious ones.
Don't sit down at a restaurant on a first date, order your drinks, and immediately launch into rapid-fire questioning or there may not be a second date what a total disappointment if you liked their answers! Once you both know you're interested in learning a lot more about one another, consider having a more structured 21 questions with a guy conversation, whether you're just talking or including it as part of a game. You may unsubscribe at any time. By subscribing, you agree to the terms of our Privacy Statement. The questions you ask on a first date will make or break the vibe as you get to know each other.
If you want your date to go well, study these questions beforehand. The right first date questions will help you make the best impression possible. Who do you aspire to be like? What was the last book you read without skipping through anything? What is the weirdest scar you have and how did you get it? If you could trade lives with one person for an entire day who would it be and why? Do you believe in ghosts?
Shark diving, bungee jumping, or sky diving? Which would be harder for you to give up: How did you meet your best friend? Do you have a sweet tooth or a savory tooth? What accomplishments are you most proud of? What is your favorite Wikipedia article? What is your favorite physical attribute about yourself? What is one of the weirdest things you used to do as a teenager?
Gin, vodka, or tequila? What drives you to do what you do? What kind of phone was your first cell phone?
What did you love most about the place you grew up? What about it did you love the least? What trajectory are you hoping to push yourself onto? Where do you want to head? What is your most bizarre talent? Is there a documentary or book that really changed the way you thought about something? Have you ever used it for real? Can I get you another drink? Then try to guess which one is a lie. If you could write a note to your younger self, what would you say in only two words?
21 Revealing Questions to Ask a Guy
If you had to name one thing that really makes your day, what would it be? What is a misconception others often have about you? Whats the most valuable life lesson you have learned because of a mistake? Read anything interesting lately? You want them to tell you so you can avoid it ; What is 1 thing in your life that you are not doing that you wish you were?
What do you do when you feel like giving up?
Now, you might get some pushback from the guy you’re dating.
If you could only keep one book you currently own, what would it be? What are you most excited about in your life right now?
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Describe one extravagance you have for which you will never apologize. What do you want to be known for? In one sentence what is your biggest concern right now? What do you feel people take for granted the most? What are you better at than 90 percent of the population? What is something about you that would surprise me? What is a piece of advice you often give but find yourself struggling to follow? Describe your perfect mate in one sentence.
When is the last time you did something courageous for yourself? Would you describe yourself as more of an optimist, a pessimist, or a realist? Which significant other in your life has had the biggest impact on you and why? If you had to spend a year alone with one other person who would it be and why? What was the last thing you learned that made a big impact on you or an ah-ha moment? When was the last time life left you breathless?
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What are you really passionate about and why? Where is your favorite travel get-away? If you had one hour left to live what would you do? What was your favorite year and why? Do you have any tattoos? What do they mean? If you could come back to life as an animal what animal would you be? If you could be friends with a celebrity who would it be and why? Have you ever laughed so hard you peed your pants?