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50 Cheeky, Personal Questions to Ask Someone You Like

A great way to get someone interested in you is to get them to talk about themselves. Here are 50 fun, personal questions to help get you started.

personal questions

A psychologist at the State University of New York at Stony Brook wanted to know how people were able to form romantic relationships with strangers they just met.

Arthur Aron had an hour to create intimacy levels between couples usually done over the course of weeks or months together, so he decided to create a set of questions that could elicit this type of connection.

At the end of the experiment, he was both surprised and happy to note the subjects did feel a stronger connection to their counterparts compared to the control group.

How did he do it? By giving the couples a set of personal questions they could ask each other on the first date.

Why does exchanging personal information work?

By telling your date about some personal non-TMI stuff during the first date, you are essentially letting them get to know you better at a rapid rate as opposed to just letting the getting-to-know-you stage play at its own pace.

By asking personal questions immediately, you are essentially hacking your love life. But we’re not complaining. You’re not being duplicitous by trying to make your date like you better, you’re actually doing the opposite by telling them all about yourself.

When a person finds out something personal about you, they will be able to sympathize or empathize with you. These two components are what makes relationships work. If they don’t exist within a relationship, new or otherwise, there’s little to no chance of ever making a connection.

So, what do you do? You either cultivate a connection using personal questions or express yourself by sharing these personal things during the conversation on the first date. [Read: Try these 60 get-to-know-you questions for a new romance]

What types of personal questions can you ask?

Now, this is the tricky part. There is such a thing as too personal. Some questions might be inappropriate and there are also some things best left said on the first date. Here’s a brief guideline for you to follow. Do not ask anything about:

#1 Bodily fluids. Save that for when you start sleeping together.

#2 A death in the family. Let them express themselves about this on their own time.

#3 A mental disorder. Neither of you should really discuss this without consulting with a professional.

#4 Salaries. It’s just too tacky.

#5 Past relationships. You do not want to go there. Yet.

[Read: 14 awkward questions you should never ask a guy]

So, what sort of questions should you ask?

The questions you ask should be based on things that will show you what type of person you’re dealing with. Although this is not an interview, it is still a way for you to gauge how they react to certain topics and how they express themselves—either honestly or with reservations. No matter what they say though, the very act of sharing will definitely help you grow closer. Here are some examples you may use during your first date:

Note: Keep the conversation going by asking an open-ended question like, “Why?”

#1 Where did you grow up? What was it like growing up?

#2 What are your siblings like?

#3 What about your parents?

#4 Who do you admire the most right now?

#5 What was your favorite subject in college? [Read: 20 revealing questions to get to know someone better]

#6 How’d you meet your best friend?

#7 If you had a free plane ticket, where would you like to go?

#8 Aside from the job you have now, what sort of work would you like to do?

#9 What’s the best part of your daily routine?

#10 What random topic do you enjoy discussing?

#11 If you could compete in any sport or competition, what would it be?

#12 If you had an infinite amount of resources, how would you use it to change the world?

#13 Describe your perfect man cave/she shed. *The recently coined term for the female counterpart to the man cave.* [Read: 40 questions to ask your crush and subtly flirt with them]

#14 Why do you think a lot of people are finding it hard to find relationships?

#15 Who is your favorite superhero?

#16 How was your life in school while you were growing up?

#17 How was your relationship with your grandparents? Would you have changed anything?

#18 Describe the best day of your life—one that has already happened.

#19 What would you like to change about your friends?

#20 How do you express yourself romantically?

#21 What’s the most important thing in your life right now?

#22 What was your most embarrassing moment? [Read: 40 first date questions to have a fun conversation together]

#23 What’s your biggest fear?

#24 What’s your pet peeve?

#25 What’s the first thing you bought with your first paycheck?

#26 What’s the most offensive thing anybody has ever said to you?

#27 Which one of your parents do you like most?

#28 How did you end up working in your job right now?

#29 What little thing makes you extremely happy?

#30 What do you love about this city?

#31 Where is your most favorite place here?

#32 Who do you first look for when you encounter a problem?

#33 If someone gave you a blank check *funded, of course*, how much would you write it for, and what would you spend it on first? [Read: 50 questions to immediately know if someone’s right for you]

#34 What’s a song that moved you to feel something?

#35 What movie made you cry?

#36 What movie made you laugh so hard you cried?

#37 Where would you like to live for the rest of your life?

#38 How often do you find yourself thinking about your life?

#39 What would you like to change in your life right now?

#40 What advanced college degree would you have liked to study?

#41 What do you think is the best profession in the world? [Read: How well do you know me? 35 fun questions for new couples]

#42 What’s the best toy you ever got as a kid?

#43 What was the worst lie you got caught in?

#44 How would you comfort someone who was depressed or in pain?

#45 How expressive are you?

#46 What do you do when you’re sad or in pain?

#47 How would you like to be comforted or helped?

#48 How do you start your day?

#49 Do you think you could own a plant and not let it die?

#50 What do you think about dogs?

[Read: 36 racy, random funny questions for flirty guys and girls]

Red flags to watch for

Even though these questions aren’t prying, some of them could trigger negative reactions. Or, they could also signal the person you’re with is being less than honest.

#1 They close off their body by crossing their arms, turning away, or leaning back.

#2 They change the subject.

#3 They answer with, “I don’t know,” refusing to elaborate further.

#4 They answer with a very obvious lie.

[Read: 10 questions that will usually turn anyone off from answering them]

Now that you know how to get up close and personal with a date, it’s time to try it out on your next one. We hope these tips and personal questions can help you find the love of your life or at least your love for the night!

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Danielle Anne
Those who can’t do, teach. I can neither do nor teach as well as others, but I can try. Aside from being a writer, I am also a physical therapist. My dream is...
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