“Is there something you’ve always wanted to learn?”
Asking this question can help you learn about their interests and hobbies. We all have that one project or activity we’ve always wanted to start but never did. Ask them about theirs to see if they have any hidden interests. Use this knowledge to your advantage in the future by setting up a date around their interests. If they’ve secretly wanted to learn how to paint their whole life, surprise them with a date to a painting class! Be their special someone by giving them a meaningful memory they won’t forget.
“Where is your favorite place?”
Their answer to this question will tell you where they call home. Questions about their favorite locations can give you a glance at what they call their “happy place,” and what types of surroundings they prefer. Is this place somewhere nearby? A childhood home? A beach? A nature trail? Knowing what settings they enjoy most can help you in the long run. When planning a future date or getaway, remember their favorite spots. If they enjoy a specific hiking trail, plan a special hiking excursion to their favorite spot. If they love beaches, book a romantic beach getaway to get them in the mood. On this vein, you can also ask a more specific question, like "Where did you grow up?" or "Where did you go to college?"
“What’s something you’re proud of?”
This question is a great way to learn about their ambitions. Accomplishments can tell you a lot about a person. Are they proud of a recent purchase? Did they get college scholarships they were proud of? By asking questions about their accomplishments, you learn about what they value and what they hope to do well in the future. If you don’t know where to start, try asking these questions: “Have you won any awards?” “What recent decision has made you happy?” “Who do you call first when you get exciting news?”
“What’s a random fact about you?”
Their answer to this question will show you their silly side. We all have interesting and quirky things about us. These little facts don’t often come up in regular conversation, so this is a fun question that will have you both learning more about each other. Follow up with questions like: “What’s the craziest thing you’ve ever done?” “Do you have a hidden talent?”
“Where do you see yourself in five years?”
This question will give you the chance to learn about their dreams and goals. Knowing where a person sees themselves in the near future can help you understand their short-term and long-term goals. This will also give you the chance to see if your goals are compatible with theirs. Ask them if they see themselves going back to school, getting a pet, or moving sometime soon. Do their future goals align with yours?
“Have you ever wanted to be famous?”
This question gives you a glimpse into their wildest dreams. Most of us have had a point in our lives when we wished we were in the limelight. This question will add some fun to your conversation while also telling you more about your date. If they’re shy, maybe they’ve never thought about being famous before. If they’re more outgoing, it may be a question they often think about. If they have thought about being famous, whether in their past or recently, keep asking them questions. “Would you want to be a famous singer? Athlete? Actor?” “What would be your favorite part about being famous?”
“What’s something you’ve always dreamed of doing?”
Ask them about their passions with this question. When talking about a lifelong dream or goal, a person lights up. If you know what they’re passionate about already, you can take this question to another level by asking about a specific dream or hobby. You can also ask “What are your hopes and dreams?” Keep your date’s response in the back of your mind for future date ideas! If your date has dreamt of riding a horse, surprise them with a horseback riding lesson. If they are passionate about baking and dream of opening a bakery, take them on a roadtrip to visit bakeries in your area.
“What does your perfect day look like?”
Asking them this question can help you understand what they value most. The question may seem simple, but a person’s “perfect day” can tell you a lot about them. How they visualize their day can tell you what they value most in life. As they describe the ideal day, pay attention to what they focus on most. Do they look at the day as one big picture, emphasizing the large tasks of the day, or do they appreciate the smaller things in life like what they’ll have for breakfast?
“Would you rather…?”
This question is an icebreaker and game built in one that will help you get to know them better. “Would You Rather?” is the perfect game to play if there’s a lull in the conversation, and it’s a great way to get to know someone better! How will they respond when faced with the silly and often difficult choices of “Would You Rather?” Give them choices that are fun but also a bit complex. Here are some questions to get you started: “Would you rather be able to talk to animals or speak another language fluently?” “Would you rather drink Pepsi or Coke for the rest of your life?” “Would you rather only listen to music from the past or music from today?”
“What’s your favorite joke?”
Asking this question can help you know their sense of humor. Are they into dad jokes or knock-knock jokes? Are their jokes funny or are you laughing more at how ridiculous the joke is? Either way, this question is bound to get you both giggling. Ask this question if you don’t know what to say next! This is a great icebreaker that’ll have you both smiling and feeling more comfortable with each other.
“What would you do if there was an apocalypse?”
This random question will take them by surprise. Your date’s natural reaction and response can tell you a lot about them! Will they play along with a hypothetical situation? Will they be tactical or emotional when facing a zombie? Think about what you would value most in a partner if you did find yourselves in an apocalypse. Would you want them to throw themselves in front of hungry zombies for you, or would you want them to help you run as far away as possible? Have fun and try not to think too hard about the logistics. See where your imaginations take you!
“If you could have a superpower, what would it be?”
Their answer to this question can help you learn about their fantasies. This silly icebreaker is the perfect way to learn more about them! Spark a conversation about your favorite superheroes, and instigate a lively debate about what superpower is superior. You may even be able to uncover more about their personality. Wanting a superpower that’ll turn them invisible may mean they’re a bit mischievous. You can work with this! Do they want to be invisible to be a fly on the wall, or do they want to pull secret pranks on people? The ability to fly may mean they are captivated by thrills. Ask them if they’ve ever been on an adventure that made them feel like they were flying like ziplining or skydiving.
“What’s something that gets on your nerves?”
This question is a great way to learn about their pet peeves. We all have things that bother us, and knowing about what gets under your date’s skin can help you avoid awkward situations in the future. Getting to know your date means getting to know all sides of them. Start by talking about what bugs and irritates you, and then ask your date about what bothers them. It’s always best to be honest upfront, and they will be more comfortable opening up to you if you initiate the conversation. Are there a lot of things that bug your date, or are they rather laid back? Your date’s response can help you figure out how they handle stressful situations.
“What’s the most embarrassing thing that’s happened to you?”
Asking this question can help you understand their past. We’ve all done something that was painstakingly embarrassing in the moment but is now hilarious looking back! Laughter is the best medicine, and it’s always good to laugh at ourselves every once in a while. Don’t be afraid to ask them about their embarrassing moments while opening up about yours. Asking them about their own awkward moments can open up the floor for deeper conversations, letting you connect and get to know them better. When we talk about our most embarrassing moments, we show vulnerability, humility, and humor, making this a great question to ask someone you’re dating.
“What’s your dream job?”
This question can start a conversation about their career goals. Maybe they already have their dream job or they’re moving toward their ideal career. Either way, knowing what they hope to achieve in their career can help you get to know their interests and passions better. As you learn about their dream job, ask them questions about it. “Why is it your dream job?” “What started this passion?”
“If you could travel anywhere, where would you go?”
Asking them about their dream destination can help you learn about their lifestyle. Are they an active traveler wanting to travel the world, or are a homebody looking for adventure in their hometown? Their answer will give you an idea if your lifestyles match. If they don’t match, no worries! Who knows? Maybe you’ll be able to share your ideal adventures with each other. There is a yin-yang after all.
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