10 Hilarious And Unexpected Questions To Ask On A First Date

First dates? They can be awkward, fun, horrible, or hilarious. Make sure you have some interesting lines to break the ice and have a good conversation to figure out what the other person is really like. Just try asking these ten unexpected questions to spice things up when you’re gearing up for a first date.

Do You Cook Well All The Time Or Just One Dish?

We all have our signature dish. Some are the go-to experts for a specific meal, while others get creative in the kitchen. If you’re wondering how comfortable your date is in the kitchen, this question reveals whether they’re a one-dish wonder or a culinary explorer. Either way, it’s a good icebreaker.

Are You The “Good Cop” Or The “Bad Cop”?

How do they handle tough situations? If they’re more about smoothing things over and keeping the peace, they might lean toward the “good cop” role. On the other hand, if they’re more direct and assertive, they could be the “bad cop.” Isn’t it a smart way to check how they like to deal with life’s challenges?

Do You Like Backhanded Compliments?

Some people appreciate a little sarcasm, while others prefer straightforward compliments. Ask this question and see if your sense of humor matches. A comment like “You’re pretty cute for someone so early in the morning” could be a hit or a complete miss. It depends on their reaction.

How Do You Feel About Killing Bugs?

Bugs tend to bring out mixed reactions—some ready to swat, others determined to spare. Your date’s take on this tiny dilemma can offer surprising insights into how they handle life’s little curveballs and might even spark a few laughs along the way.

What’s The Worst Fashion Trend You’ve Ever Tried?

Fashion is all about experimentation, right? Everyone has that one trend they regret trying. Maybe it was neon colors or oversized everything—who knows? Asking this question opens up a chance to laugh together about the trends that seemed like a good idea at the time. It also shows you how they view personal style.

Are You A Good List-Maker?

Your date may like things organized and keeping everything on a list. But what if you prefer winging it and seeing where things go? That’s why you need to ask if they are a list-maker. It can tell you how they take on responsibilities and tasks. You might find out whether they’ll be prepared for the next date.

How Do You Feel About Aliens?

As soon as you ask about extraterrestrial life, their expressions will speak louder than words—skeptical or fascinated. This question also opens up a fun, offbeat discussion. Their answer could lead to a conversation about the unknown, space exploration, or just what makes them curious about the world beyond.

Who’d Be Your Sidekick Animal?

Imagine the possibilities! A question like that will let you tap into their imagination and see which animal they’d pick as a partner in crime. Whether they choose a loyal dog, a moody cat, or a free eagle, their answer will speak about their personality and maybe even reveal their ideal adventure buddy. 

Do You Like To Drink?

That’s a good question to understand if your hangouts could include wine tastings or cocktail experiments. When you know your date’s drink preferences, it can tell you about their social habits. Moreover, this is not just about alcohol. Some people are into trying out new non-alcoholic beverages, too.

What’s Your Ideal Sunday Like?

People have different ways to unwind. You may enjoy a lazy day with a book, but your date might like to spend the day hiking or exploring. So, if you mingle, you can discover how you would be spending weekends together. Adventure or relaxation—their answer will give you insight into their vibe.