You want the guy you like to open up to you, but at the same time, you don’t want him to get the feeling that he’s being interrogated. The best way to get into your his head and spark conversations is to ask fun and interesting questions that get him talking. These lighthearted questions will help you go beneath the surface and get to know him better.
Have you ever cheated on a partner, why, and did they find out?
This question is interesting on so many levels. It’s personal, but not too personal. And it allows him to respond with as much detail as he likes. The way he answers this will tell you whether he’s the kind of guy who thinks cheating is a big deal or not.
Is there any game you were/are really good at playing?
Maybe it’s a game he enjoyed playing as a kid and could kick everyone’s ass at. Or it could be a game that he dominates as an adult. If he’s the gamer type, he’s sure to love answering this and bragging about his skills.
What’s your favorite/worst thing about yourself?
Are you dating a super cocky guy, a man who displays a healthy dose of humility, or one who enjoys putting himself down? This question will help you find out while giving an idea of how he sees himself and how self-aware he is.
Have you been caught having sex before?
One time, I forgot to lock my doors and a guy I was seeing casually walked in on me and another guy in our birthday suits doing the nasty. It’s one of the most awkward experiences of my life but the story is hilarious every time I tell it. If he’s had an unfortunate moment like that, he’ll probably have fun sharing it with you.
What’s your desert island movie or TV show?
People love talking about their favorite things including that movie that they can never get tired of watching. I can talk for hours about how much I love Grey’s Anatomy or the American version of The Office. I’ve seen them dozens of times, to the point that I can narrate entire episodes word-for-word. This question is bound to have him rambling about his favorite film or TV obsessions.
Ever been on a bad date?
Almost everyone has a story about a date from hell. A date where nothing goes the way it’s supposed to and you just can’t wait for the night to be over. He’s going to have a lot of fun recounting his experience to you. And if you’ve both been on several terrible dates, you can trade stories back and forth until it hurts to laugh.
What have you done that you’re most proud of?
This will tell you what brings him fulfillment. You’ll learn what drives him and how he defines success and achievement. Once you can get him talking about his passions, it’ll be easy to drive the conversation towards other subjects.
Is there a movie title that best explains your current life?
The movie title to my life right now would probably be “I’m Thinking of Ending Things,” because I’m sick and tired of this pandemic and worrying about getting the virus. Whatever his answer is, it’ll give you an idea of the state his life is in at the moment and probably lead to a deeper conversation.
What non-sexual thing turns you on?
This is a slightly naughty question, but it’s not too dirty that it crosses a line, especially if you haven’t known each other for too long. It’ll give you an idea of the silly, out-of-the-box things that move him. This way, you’ll know how to get him fired up without taking the usual seduction route.
When you were a kid, what did you dream about doing?
I wanted to be a lot of things when I was little. I changed dreams and careers every month. Even now, it’s fun to think about those days and all my innocent ambitions. This question is going to get him to reconnect with his inner child and travel back in time so be ready for a flood of nostalgia.
What’s a great or useless talent that you have?
Your guy may have hidden talents that will surprise you, but you might not learn about them until you ask. Maybe he can play the piano like Mozart or contort his body into impossible shapes. Whatever amazing or silly skill he has, here’s your chance to find about it. And if you’re lucky, he might even put on a special talent show for you.
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