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You can use these 3 types of questions as conversation starters while slowly getting your answer.

3 Types of Questions to Ask

How much a person knows you will depend on how long you’ve known each other, how observant he/she is, and how open you are to this person.

So if you wish to know if they only know you on a surface-level or not, here are 100 questions you can use to find out:

1. Light and Fun

These questions answer details about you that you let people see on a surface-level. Even your work colleagues and acquaintances could know your favorite lipstick color or hairstyle, your birthday, and other personal tidbits just by seeing you regularly.

Let’s begin with light topics that tackle the fun things about you:

  • Do I like my hair long or short?
  • What’s my favorite alcoholic drink?
  • Am I a morning person or a night person?
  • Which ice cream flavor is my favorite?
  • Do I love coffee or tea?
  • What is my favorite color?
  • Is my handwriting good?
  • How many siblings do I have?
  • Am I a dog person or cat person?
  • Do I have a favorite shirt?
  • What is my job?
  • How old am I?
  • Do I prefer Pepsi to Coke?
  • Name one song I loved in the last 10 years.
  • Which rock band is my favorite?
  • Do I play any instrument?
  • What dessert do I love the most?
  • Do I dye my hair?
  • When is my birthday month?
  • What recent TV show did I go crazy for?
  • Am I a fan of karaoke?
  • How do I like my eggs?
  • What is my go-to pair of shoes?
  • Who is my best friend?
  • Do I eat out often?
  • What is the color of my eyes?
  • Do I know how to whistle?
  • When it comes to clothing, do I go for plains or prints?
  • What sports do I play?
  • Where do I work?
  • Do I go to the gym?
  • Which is my favorite restaurant?
  • Am I left-handed or right-handed?

2. Deep and Serious

These questions dig into deeper-level facts or behavior you shared with your friends or partner through the months or years they’ve known you.

If you’re a morning/night person, what drink makes you drunk the most, and how generous or cheapskate you are when it comes to Secret Santa’s are good examples of questions that can be answered by people you’ve known for years.

  • Who was the first person who broke my heart?
  • Am I close with my siblings?
  • What’s my favorite holiday?
  • Do I have a target retirement age?
  • Have I ever broken a law and gotten away with it?
  • Am I closer to my mom or dad?
  • What occasion do I love the most?
  • Do movies make me cry?
  • Where is my favorite summer destination?
  • Would I pick skiing or fishing?
  • How many times do I check my phone?
  • Can I ride a bike?
  • Do I have tattoos? If so, how many?
  • Have I ever sent a meal back to the kitchen?
  • What is my favorite book of all time?
  • Can I snap my fingers?
  • Do I like superhero movies?
  • What unique skill do I have?
  • Do I love or hate clowns?
  • Am I allergic to any food?
  • Who do I look up to in my profession?
  • Have I ever gone hiking before?
  • What is the latest TV series I binged-watched?
  • Where do I like spending my birthdays?
  • Am I religious?
  • Who was my first crush?
  • What is my go-to comfort food?
  • Which book made an impact in my life?
  • How many kids do I have/plan to have?
  • Who is my favorite cartoon character?
  • What does my ideal weekend look like?
  • Do I love to sing/dance?
  • How many pets have I had in the last 5 years?
  • What is the biggest lie I have ever made?

3. Values and Memories

These questions would definitely prove that your friends or partner knows you a LOT.

Unlike the previous personal tidbits, these details cannot be known just by mere observation. Understanding your personal values and sharing memories would take a lot of lunch-outs, vacations, sleepovers, and occasions to get to know a person this much.

  • What’s the funniest Secret Santa gift I ever received?
  • Do I have a favorite childhood story that I love retelling?
  • Which of my siblings am I close with?
  • What’s my biggest pet peeve in relationships?
  • Is it my dream to travel around the world?
  • Have I lost anyone close to me?
  • What’s the biggest achievement I’ve ever made so far?
  • Do you know of that song that makes me irritated?
  • What is the longest road trip I’ve ever been on?
  • Did I go to public or private school?
  • How long can I go without my phone?
  • What outfit did I swear I’d never wear?
  • Do I consider myself healthy?
  • How old is my dream retirement age?
  • What makes me ugly-cry?
  • Where do I see myself in 5 years?
  • Am I a fan of Disneyland?
  • What is my idea of a romantic getaway?
  • Do I believe in the afterlife?
  • What’s the strangest gift I’ve ever given you?
  • Which of my body parts do I hate the most?
  • How many times have I ever been married?
  • Who is my go-to person when I’m feeling down?
  • Do I regret anything huge that made an impact in my life?
  • How did my last relationship end?
  • What is the most controversial opinion that I have?
  • If I could choose my cause of death, what would it be?
  • Have I ever been depressed in my life?
  • Am I OK with spending my last days in a retirement home?
  • Which food is my specialty dish?
  • What was the most embarrassing thing that has happened to me?
  • When was the last time I had to be admitted to the hospital?
  • Have I converted religions before?
  • Which of these do I value the most? Health, Family, Friends, Career, Money?
  • What is the happiest day in my life so far?

✍️  September 24, 2020

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