16. What is one thing that always cheers you up?
This is a lighthearted question that also gives you useful information and can lead to him sharing experiences with you about when someone’s cheered him up … or made things worse. Maybe he needs a hug when he’s down, or maybe he needs to be left alone. Some people are cheered up by little notes or being listened to.
17. The house is on fire, which three things do you grab?
This is a fun exercise that will also tell you his priorities. Does he save old family photos? His gun collection? His cat? Maybe his priority is not saving anything but the people in the house, because stuff doesn’t matter to him. Maybe you’ll learn he’s actually been in a house fire and had to make this decision in real life.
18. What is one thing you can never get enough of?
Is it sex? Beer? Bacon? Or is it accomplishing things in his career? His children? You never know what will come out of his mouth, but it might be what you least expect.
19. What is the best and worst part about being a guy?
This is an incredibly revealing question. Maybe he’ll tell you his man parts are very awkward and inconvenient at times, or that he hates constantly being asked to do the heavy lifting in every situation.
You may learn that his favourite part about being a guy is that he loves traditional gender roles, being able to take care of a woman by opening doors and paying for things. Or this may be his worst part about being a guy! You never know.
20. Is there anything you’re superstitious about?
Is he all science and no superstition, or is he open to the idea that there are sometimes unknown factors driving things? Does he get uneasy if a black cat crosses his path or he walks under a ladder, even if he knows that’s ridiculous? Here’s where you learn if he’s uber rational or has a less logical and more open side to him.
21. Which do you prefer: a good book or a good movie?
This question can lead to so much more. If it’s a good book, when did he first start to love reading? What kind of books does he like? When does he like to read? And if it’s movies you’ll learn if he’s all action hero or sci-fi nerd or a little bit of both.
22. If you could be fluent in one language, what would it be and why?
Asking this type of questions to a guy will give you a chance to see what part of the world he’s interested in and why. Does he want to learn French so he can go to France on his next vacation, or Spanish because it will come in handy at work or in volunteering? Or maybe he wants to learn Farsi so he can read poetry in the original language. This question can lead to any number of answers depending on the guy you’re asking.
23. Have you ever dreamed of being famous?
Is he the kind of guy who’d like to be on “Love is Blind,” baring his soul to the world, or is he more introverted? Or maybe he’s interested in a different kind of fame—he wants to be an actor, or gain fame by doing something noble like contributing to the discovery of cures for incurable diseases.
24. What’s your biggest guilty pleasure?
What equals pleasure for him, and why is it guilty? Does he have a hard time picking among several guilty pleasures, or does he not believe there’s any such thing?
25. If you had three wishes, what would they be?
Is it money, fame, love? What would he do with them if he had them? Does he try to cheat and ask for more wishes? Will he share his wishes if you want one?
26. What is one subject you wish you knew more about?
This will tell you about his aspirations. Would he like to know more about flying so he can get his pilot’s license? More about what’s going on in the news and in the world so he can keep up when talking to people at parties? More about the line of work he’s in so he can advance in his career? Or more about some random hobby that’s just for fun?
27. What skill do you wish you could master?
Does he have a dream to learn knife throwing? A foreign language? Stand-up comedy? People are interesting and you never know what to expect.
This can be a fun question to see both what his interests are, how he does or doesn’t work to achieve goals, and what’s important to him. He might talk about something he really sees himself mastering or he might talk about a far-fetched dream, and that will tell you something about who he is.
28. What is one temptation you can never resist?
Maybe he’ll tell you there’s nothing he can’t resist—he’s a paragon of virtue. Or maybe he’ll keep it light and tell you chocolate, or he’ll make it sexy and tell you lingerie. Or possibly he’ll tell you that when it’s fishing season and incredible weather he can’t resist playing hooky from work on Fridays to get away for the weekend with his buddies.
I hope this article gave you some fun and fresh ideas for questions to ask a guy to really develop a connection.
Written by: Sabrina Alexis Originally appeared on: A New Mode Follow Sabrina on Instagram and subscribe to her YouTube Channel - https://www.youtube.com/anewmodechannel