Asking questions to get to know someone can add a bit of excitement to that awkward phase. You don't want to just ask anything though. Instead, use harmless, fun getting to know you questions before peeling back the layers to learn about childhood dreams and future plans. The way that you ask the questions is also important.
Don't Just Say Anything
As fun as it can be to wing it in conversation with someone you're just getting to know, it can also set you up for shyness, awkwardness, self-doubt, or the nagging fear of saying the wrong thing (a faux pas or just something boring). "What if this person doesn't find me as interesting as I find them?" might end up going through your head if you don't show up prepared, and that's when some forethought can help. It's worth it to take the time before a date (or before a party, even) to come up with some unusual but fun questions to get to know someone, so you stand out and keep the conversation flowing. Just remember to keep the focus on the other person for best results.
Harmless Surface-Level Questions
Whether you love it or hate it, sometimes small talk is necessary and you need great questions to ask someone new when you're first starting to get to know someone. Asking innocuous questions until they warm up to you and want to open up more will pass the time and keep things light and fun.
What is your favorite flavor of jelly bean?
What's your favorite Christmas movie?
If you could live in any period of history when would it be and why?
Tell me 10 things I'd see when I walk in your door?
What kind of celebration would there be on a "St. YOU" day?
Who would play you in a movie about your life? Who would play me?
Give me three words that describe you.
What was the best birthday you ever had?
If you were a ghost where would you haunt? Why?
What kind of car did you wish you had when you were a kid? What about now?
What's your favorite 1950s rock song?
Which one would you choose to watch: Family Guy or South Park?
In a zombie apocalypse, what would be your weapon of choice?
What is your favorite video game?
What is the worst thing you've ever purchased and why was it so bad?
Snapchat or Instagram?
What's a movie you can practically quote from start to finish?
You look great! What's your fitness routine?
Questions to Peel Back the Layers
Once you've chatted about favorites, fitness routines, and pop culture, you can dive into some deeper topics and ask questions to get to know someone better on a different level. Get to know their childhood, hopes and dreams, the type of person they are, what makes them laugh, and what makes them proud (or scared) with these types of questions.
If you could go back in time and make little changes to your childhood, what is one thing you'd learn and master over the years so you'd be an expert at it today?
If you were lost in the woods, how long do you think you'd survive? Why? What special skills would you put to use?
If you had to make an iPod playlist named after me, what songs would be on it?
What's one job you would never do?
How would you describe your sense of humor?
What's a random award or recognition you feel you deserve?
What is your favorite thing to create?
If you could take a week off from your regular life to immerse yourself in learning something new, what would it be?
If you were to write a book, what kind would it be?
What's something you wish people automatically knew about you? Name something about yourself you wish you could just put on a T-shirt so you could get it out of the way when meeting new people.
What is something you avoid at all costs? Is it a fear, aversion, or is there a special story behind your answer?
What is one thing you wish you were better at?
When was the time you felt most free?
Funny Get to Know You Questions
Asking silly questions to get to know someone can be a fun way to liven up a date. Check out their sense of humor and see what types of creative answers they come up with when they answer these questions.
If you could shrink down any animal and carry it around in your pocket, which one would you choose?
What's the weirdest nickname someone has for you and what's the story behind it?
What's the silliest thing you've ever done in public?
If you had to sing everything you wanted to say, what would be the most awkward time to say something?
How quickly do you go through an entire box of cereal?
Have you ever eaten so much that you had to relax afterward?
Do you ever talk to yourself when you're alone? What's the weirdest thing you've said to yourself?
Have you ever embarrassed yourself while home alone?
If you could only eat either donuts or chips for the rest of your life, what would you choose?
If you could take out a bad day on a household item, what would you choose?
Techniques for Asking Questions
Don't just think of a long list of random getting to know you questions to ask rapid-fire and go for it. Think of how you ask them and how you listen to the answers, too.
Ask questions that invite sharing. They can share the names of a few songs on their iPod playlist and then you can show them yours. You can then discuss music and your favorite bands or songs, or talk about concerts you've been to or wish you hadn't missed.
Think about how you ask the questions. While you don't want to be an interrogator, asking question after question, make sure to lead the conversation back around to them, and ask another fun question. It's also a good idea to ask open-ended questions to get to know someone, so it takes more than a "yes-no" or one-word answer to respond. If it is a short answer, such as a movie title, follow it up with "Why did you like that movie?" and let them talk about it. "Why" and "how" will be your best friends when you're trying to get to know someone.
Plan ahead. Read the news or trending articles on social media before you meet up with the person so you can ask what their thoughts are on those topics. You may want to leave politics out of it, at least at first. Tread carefully on those! Try to skim a variety of topics so you're not stuck with a mind full of fresh celebrity gossip when they would be much happier sharing their thoughts on the latest breakthrough in science or technology.
Be genuinely interested in them. Don't spend your time trying to think of what you'll say next. Stay engaged and listen to their answers. What to ask next will flow naturally, and the person you're getting to know will be more willing to share their thoughts with you when they sense you want to hear them.
Find out some of the basics of what they're most interested in and give yourself a crash course just so you're familiar enough with their favorite subject (or subjects) to ask the right questions and get them talking. It's fun to see someone light up as they talk about something they're passionate about, and you may learn something new. Don't pretend to be an expert or lead them to think you share a hobby when you don't. Just making an effort to learn a little about what they're interested in will show them that you're interested in them, though.
Think about some of the things you wish people knew about you. What types of questions could someone ask you to find these things out? Ask your date similar questions and see what they reveal.
A Verbal Game of Catch
Fun questions can only come if your conversation is like a friendly game of catch, with the ball going back and forth between you. As you get more and more familiar with each other's conversational style and personality, the questions and conversations can get more esoteric and daring. A fun question is a question that makes the person think and gives them the opportunity to express themselves to an eager audience: you.
