115 Online Dating Questions to Ask Your Crush

Couple sits at dinner together, the women looks at the mens phone excited

You’ve found someone online you’re intrigued by – now what? The next stage is normally checking your compatibility with your love interest by asking lots of dating questions. So being well-prepared with the best questions to ask your crush will help spark an engaging conversation.

However, getting to know someone by asking questions may sometimes feel like a job interview. When you find someone online who seems appealing, it can be challenging to keep the conversation going without sounding like a bore. Thankfully, having a stack of interesting questions to ask someone can help break the ice.

The benefits of having fun questions ready

Women in a blue jacket walking outside while calling someone, she smiles.
There are hundreds of online dating questions that you can use to find out various things about your crush. And asking the right questions can help you get a better understanding of how well you mesh. If you have a crush that you have your eye on, preparing ahead of time can help. Of course, you may sometimes fall back on the old standard questions about their favorite color, food, or movie. However, using fun and intriguing questions will pique your crush’s interest and help you stand out from the crowd. This way, you can get them into deeper, more meaningful conversations. Their answers to your questions can:
  • Give you an idea of their temperament
  • Indicate if you are compatible
  • Reveal similar hobbies and interests
  • Pinpoint common values
  • Provide an understanding of their beliefs
  • Show their intentions
  • Aid in your decision to move the relationship forward
  • Highlight their quirks
In addition, you will come across as a great conversationalist, helping you to grab the attention of that special someone. As a result, having cool questions to ask will prompt your crush to reciprocate and ask you questions in return. If your crush has difficulty keeping the conversation going, they can use the same questions for you. Therefore, be ready with some terrific answers for yourself.

Questions to ask someone you're dating

If you are looking for excellent questions to ask on a date or some deep relationship questions, this list of 115 different options can keep you and your crush talking late into the evening.

Engaging topics to talk about with a guy

Women and man on a date, talking and thinking

Sometimes the questions come easier when you narrow down the subject matter. Once you determine your crush’s interests, you can continue with follow-up questions.

Some engaging topics to chat about include:

  • Politics
  • Religion
  • Finance and investments
  • Environmental issues
  • Current events
  • Sports
  • Art
  • The theatre
  • Music industry
  • History
  • Likes and dislikes
  • Hobbies and passions
  • Hopes and dreams
  • Personal memories
  • Travel
  • Cuisine
  • Books
  • Technology
  • Podcasts
  • Games
  • Annual holidays and traditions
  • Children
  • Pets
  • Fashion
  • Cultures
  • Health and wellness
  • Recreation and exercise
  • Clubs or associations

Remember that having questions in mind can help you relax when talking to your crush for the first time and as you get to know each other. In addition, planning ahead can help ease your anxiety about online dating.

Top questions to ask your crush

Women happily smiling at another women as they both sit in front of each other

If you don’t know where to start asking questions with someone new, this list of top questions is sure to get the ball rolling.

  • How would your best friend describe you?
  • Are you the favorite child?
  • Do you have a pet peeve?
  • What is your ultimate goal in life?
  • Do your friends consider you an introvert, an extrovert, or somewhere in between?
  • What would you do if you found a bag full of money and no one else was around?
  • Would you quit your job and go to Disneyland if you won the lottery?
  • What picture do you have as your phone’s wallpaper right now?
  • Who is your closest relationship with?
    What is something you would like to learn as an adult?
  • What is the most significant item you’ve ever owned?
  • How do you feel about mismatched socks?
  • Are you always on time?
  • Do you volunteer anywhere?
  • Have you tried online dating before?

Interesting questions to ask a guy

Some guys are more open to discussion than others. Therefore, using the right questions can help ease a man out of his shell.

  • What makes you insecure?
  • Who was your childhood hero?
  • What is your stance on zoos?
  • What was your first job?
  • Are you a coffee or tea person?
  • What would you need to take with you to a deserted island?
  • Do you know any other languages?
  • What makes you happy?
  • Where do you want to retire?
  • Do you prefer classic cars or new models?

Juicy questions to ask a guy

If you are eager for an intimate relationship with your crush, asking these enticing questions can open up a world of conversation between you two.

  • What is your worst first-date story?
  • What feature do you consider is your best?
  • Have you had a crush on a teacher before?
  • Do you like to be the pursuer or have someone pursue you?
  • Do you have any quirky habits?
  • Do you prefer boxers or briefs?
  • What do you want in the perfect partner?
  • Are you a boob or leg man?
  • Do you snore?
  • Would you kick me out of bed if I snored?

Fun questions to ask a guy

Young man smiling and laughing as he is calling someone

Keeping the conversation light at first can help both of you relax as you get to know one another. These questions are terrific for maintaining a stress-free chat.

  • Are you a dog or cat person?
  • What are the craziest things on your bucket list?
  • Which is the best choice, chocolate or vanilla?
  • Are you a morning or evening person?
  • Do you believe in time travel?
  • Do you take the shopping cart back or leave it in the parking lot?
  • Do you separate your colors from your whites when doing laundry?
  • Who is your longest-standing friend?
  • Do you like ice cream, frozen yogurt, sorbet, or gelato best?
  • Do you think pineapple belongs on pizza?


Questions to ask your boyfriend

If you and your crush are beginning to date regularly, finding more interesting things to talk about can be challenging. You can maintain interest by engaging your match with these questions.

  • How would you describe your parents’ relationship?
  • What’s your thought on having kids?
  • Would you consider yourself a go-getter?
  • Do you prefer to eat out in a restaurant or stay in?
  • What was your favorite subject in school?
  • Do you always put your socks on before your pants, or vice versa?
  • Is your sense of humor dry, clever, slapstick, or somewhere in between?
  • How do you deal with stress?
  • Did your parents name you after someone?
  • What celebrity does your family think you look like?

Interesting things to ask a girl

Young women with a cofee smiling as she is on a call with someone

Everyone enjoys personalized attention, so asking some interesting questions can give you a better look at your crush’s personality.

  • What is your favorite destination to visit?
  • What crazy thing makes you laugh?
  • Do you have any phobias?
  • Are there any big regrets in your life?
  • Do you consider yourself artistic?
  • What is your personality color?
  • What celebrity can you not stand?
  • Is there someone you admire?
  • What group did you run around with in school?
  • What item must you always have available?

Cute questions to ask a girl

Asking cute questions is a simple way to spice up your next conversation. So, if your eyes are set on a special girl, try using these questions to grab her attention.

  • If you could ask anyone, alive or dead, one question, who would it be and what question is it?
  • What type of animal would you be?
  • If you could live in an alternative era, when would it be?
  • Do you have any plants?
  • Do you prefer sweet or salty snacks?
  • Have you considered modeling?
  • Which armrest do you use while at the movie theatre?
  • Can you do any cool party tricks?
  • What is your astrological sign?
  • Do you believe in psychics?

Quirky questions to ask a girl

Men and women that seem to be a couple eating a donut together

Sometimes you will meet a match that is just as quirky as you. Asking unusual questions can keep your date interested in you and what your next move will be.

  • Do you believe in UFOs?
    Have you ever ridden a camel?
  • If you were the president of a new country, what’s the first thing you would do?
  • Would you shave off all the hair on your head for a million dollars?
  • What is the strangest or weirdest thing you have ever done?
  • What is the one thing in your refrigerator that shouldn’t be in there?
  • If you had to create a unique animal with superpowers, what would it do?
  • If you could instantly change your name to anything, what would it be?
  • What superpower would you want to have right now?
  • What crime would you attempt if you could go without consequences?

Romantic questions to ask a girl

Many individuals are hopeless romantics at heart. If you know your online crush is one of them or want to see if they will match your idea of romance, use these questions during your next conversation.

  • What’s an example of a perfect date for you?
  • Do you believe in true love?
  • Do you believe love at first sight is imaginary or a real thing?
  • Are your parents still together?
  • Would you prefer a beach holiday or a cottage in the woods?
  • Do you like using pet names for your partners?
  • Have you ever been in love before?
  • What makes you feel safe?
  • What gesture or action from a partner do you find most romantic?
  • What is your greatest accomplishment so far?

Risqué questions to ask girls

Depending on the circumstances of your connection, you may have an opportunity to ask some spicier questions. For example, if you are pursuing an intimate encounter, some of these questions can point you and your date in the right direction together.

  • What features do you find attractive?
  • Do you typically leave the lights on or off?
  • Would you consider yourself a great kisser?
  • Do you have any fantasies?
  • Is there any quality about me that you instantly liked?
  • What is your favorite position?
  • What is your flirting style?
  • Do you sleep in your birthday suit?
  • What one main quality do you want in a partner?
  • What celebrity would you drop everything for?

Questions to ask girls to get to know them

Women and man on a date, the women seems very excited

Getting to know someone will take time. But thankfully, many of these questions below will indicate who the person is that you have a crush on.

  • What after-school activities or sports did you enjoy as a child?
  • Where did you grow up?
  • Did you enjoy school?
  • Can you juggle?
  • If you could choose to do anything at all for a job, what would it be?
  • Who was your favorite teacher growing up and why?
  • Did you have a childhood pet?
  • What’s the most embarrassing thing that ever happened to you?
  • Did you move towns/cities/countries growing up?
  • Do you remember your first kiss?

Final thoughts

The early days of meeting new people online can be exciting. There is so much to learn about that love interest that caught your eye. But, with a little preparation, your online chatting and texting will soon evolve into dinner dates with engaging, insightful conversations.

Cheryl Wozny

Cheryl Wozny

Cheryl is a wife, mother of four, and a published author who has dabbled in many different niches for over a decade of writing. Her focus on honest and genuine connections helps provide practical information that anyone can use, regardless of their current relationship status.


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