Fun Questions to Ask a Guy That He’ll Love
Creating a connection comes down to one important thing: questions. And it seems in this digital age, the art of conversation has been lost and we don’t know how to ask the right questions to really get to know a guy. And that’s what dating is … it’s a discovery process. And the best way to discover someone and to assess how compatible you are, is through asking the right questions.
There’s a time and place for the right questions … a time to keep it light and a time to go deep. This doesn’t mean you can’t ask serious questions when you’re first getting to know someone.
There aren’t strict rules you have to follow because things like context and tone really matter. But you probably don’t want to pull out “When was the last time you cried?” on a first date (unless it somehow comes up naturally and you really get the vibe that he’s open to talking about it …)
Tone is key. Asking him “What is one thing you’re judgmental about?” can be either lighthearted or serious depending on the context, how it’s asked, and how he chooses to respond.
Some questions can lend themselves to either a lighthearted or deep response, like “What is one thing no one realizes about you?” It’s up to him to be silly or serious, and that will tell you a lot about who he is, too.
The point is, there is no formula that will tell you exactly what you can ask and when because so much depends on you, the guy, the timing, the context, the flow, etc. So what do you do when you can’t tell how receptive he is or feel uncertain about what to ask? One approach is to try asking progressively more serious questions and see how it goes.
How can you tell if you’ve gone too far? If he changes the subject he probably doesn’t like the direction you’re going. If he brushes off your question with a non-answer it probably wasn’t to his liking or it may have been too personal.
Or if he’s answering with a lot of jokes, it could be a sign he’s uncomfortable with that level of intimacy and he’s trying to lighten things up. Be observant and respectful and don’t push too far if there’s not a good flow and you’re not having fun. And remember, you should be prepared to reciprocate by answering any question you ask! It’s a two-way street, and ideally, you’ll have a good back-and-forth that’s both easy and fun.
On that note, here are 28 fun, simple, lighthearted questions to ask a guy that will make you both smile and will help you learn a lot more about him.
1. What is something you always look forward to?
Concerts? Kisses? The weekend? Travel? Morning coffee? This question can have a million different answers, all fun and easy to talk about because it’s such a positive topic.
It can also tell you a lot about him without being intrusive. If he looks forward to vacation and travel, you’ll get to hear about his cool trips and where he wants to go next. Is he a beach or a mountain guy? Is his passport expired or just renewed? Or is he a homebody who prefers a staycation? Asking such questions to a guy will give you a chance to see what you both have in common.
2. What is a random thing that reveals a lot about a person?
Here’s a question to ask a guy that will tell you the kinds of things he notices and what he thinks is important. Answers are going to vary wildly and you’re probably going to be surprised. Does he notice if someone’s fingernails are clean and make much broader assumptions about that than maybe you would? Maybe he’s more keyed into personal hygiene than you realized.
Or the random thing might be noticing whether or not someone’s got designer jeans on or expensive clothing in general and thinking that reveals a certain level of success. Maybe you agree or maybe you don’t, but it tells you something about him and his values.
3. What is a movie you watch over and over again?
A lot of us have that one movie that we can watch over and over and never get sick of. And it says a lot about a person what that movie is.
Does he like psychological thrillers? Humor? Mystery? Which characters does he love and which ones does he hate? This is a totally natural getting-to-know-you question that can tell you way more than surface information, and it leads to a low-key fun activity, watching your favourite flicks together!