By now, you probably know that asking questions is the best way to get to know someone. However, it’s hard to know what to inquire about and what topics are better left off the table. If you need a few ideas in order to have an epic date night, here are some fun questions to ask a guy that he’ll love answering.
What did you want to be when you grew up? He still might not know for sure, and that’s okay. Sometimes, our best career match happens later in life. This question is a lot of fun since it’ll remind him of his childhood in a positive way. Regardless of how or where he grew up, he still probably had dreams. It’ll also be interesting to compare what he wanted to do with what he’s currently doing now. Who knows? This question might even inspire him to go back to school or look for a better career match.
What was the first concert you ever saw? It may be something silly, or it could have been an experience that changed his life. Going to a show for the first time can be overwhelming, so it’s often quite memorable. This can also start another conversation about music, and you may end up learning the two of you have compatible tastes.
What band would you love to see live today? If they’re still active and touring, this might be a good excuse to look up ticket information. Concerts make excellent dates, and it’s always good to support your local music venues, especially after a year without live entertainment.
Who’s your favorite superhero? There’s a good chance he has one. It doesn’t even necessarily need to be someone from Marvel. It might be his mom, especially if he was raised in a single-parent household. It could also be a teacher or a sibling. There’s no wrong answer here.
What’s your least favorite holiday song? The holidays are approaching, which means that pretty soon, we’ll all have to hear the drone of “Simply Having A Wonderful Christmastime” again while standing in line at the mall. This is a good question that might get him thinking. We all know which ones make us happy, but which song would he prefer to never hear again?
What was the best gift you ever got? It could have been something he got at Christmas as a kid, or maybe a meaningful gift he received as an adult. This will help you get to know a lot about him and help you brainstorm other ideas for the future.
When was your first kiss? Now remember, this question isn’t meant to start a fight. Your guy had a life before he met you. If you’re not the jealous type, this is a fun question to ask since there’s a good chance there’s a funny story behind it. Maybe he was in elementary school, and he wasn’t expecting it. Or, maybe he was a late bloomer and had the whole thing planned.
What are the ingredients for your ultimate sandwich? Nothing is off-limits here. Make sure he answers in full. Not only do you need to know about deli meats, but condiments as well.
What gameshow will you never get tired of? Maybe he watches Jeopardy! every night but it’s never come into the conversation before. Or, perhaps he likes to watch late-night reruns of Match Game PM. He might not be into them now, but it’s amazing how gameshows are a big part of our memories. Which would he want to be a contestant on someday?
What’s your favorite sketch from Saturday Night Live? The best part about SNL these days is that you can easily watch clips of the sketches that landed the next day on YouTube. The show still has a ton of wit after all of these years, but it’s possible it was an older cast that he resonated with best. This conversation could also lead to a great night of the two of you pulling up sketches to share. This is one of the most fun questions you can ask a guy – who wouldn’t love to talk about things that make them laugh?
If you could only choose one fast food restaurant to eat at for the next year, what would it be? This question contains a lot of layers. You’d want to examine the overall menu and think hard about your choice. Once again, there’s no wrong answer for this one.
What’s your favorite dish from your favorite restaurant? Maybe it’s something from his hometown, or maybe it’s local. When you find it out, the two of you can try recreating it at home if it’s too far to travel to.
If you could live anywhere, where would it be? Don’t factor money in — again, this question is rooted more in fantasy than reality. You can learn a lot about someone based on this question. For one, you can see if they’re more of a city person or country person.
Asking a guy these fun questions will not only let you know more about him, it’ll give you plenty to talk about. Give it a try!
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