300 Questions To Ask Your Pen Pal

If you are looking for the ultimate list of questions to ask your pen pal then you are in the right place! You are guaranteed to keep the letter-writing going with this huge list!

Some of our reader’s favorite posts on the blog come from our conversation starters section. They include posts like questions to ask a girl, funny questions to ask your parents, and questions to ask your kids. So the other day I got a note from a mom asking if we could create a post about the best questions to ask your pen pal.

She told me that her daughter had recently become a pen pal with someone and she was struggling to find things to talk about to ask. Of course, I jumped on the idea because I love the idea that people are still writing letters in paper and digital form to one another!

When it comes to having a pen pal I feel like good pen pal questions are the secret to a lasting friendship. Through questions pen pals get to know one another and become more friends.

Y’all I hope you love this huge list of questions to ask your pen pal! There will be some serious questions, some silly questions, and a whole lot of variety so that pen pals can keep the letters coming for years to come!

The Best Questions to Ask Your Pen pal

• What’s your favorite childhood memory?
• What is your favorite film?
• Do you sing in the shower?
• What is the best gift you’ve ever received?
• Are you in a relationship?

• Do you prefer being indoors or outdoors?
• Do you keep a diary?
• Do you have any holiday/vacation plans?
• What do you do for work, and do you enjoy it?
• Who is your favorite actor or actress?

• Do you enjoy playing board and card games?
• Do you prefer cats or dogs?
• Can you describe your house to me?
• Who was the last person you spoke to on the phone?
• What has been the funniest text you have received this month?

• When was the last time you cried, and why?
• Have you ever broken the law?
• Can you play a musical instrument?
• What do you keep in your bag or handbag?
• Can you knit?

• How many hours do you sleep each night?
• What’s your favorite way to spend an evening?
• Who is your role model?
• If you could choose one superpower, what would it be, and why?
• Do you believe in ghosts?

• Who was your first-ever pen pal?
• How did you get into snail mail?
• What has been your favorite job so far?
• What is your favorite go-to recipe for mid-week meals?
• If you won $1 million, what would be the first thing you bought?

• What makes you angry?
• What makes you smile?
• What is your current hairdo?
• Who is your favorite band or singer?
• What’s your favorite music genre?

• What’s your favorite vegetable?
• Do you eat meat?
• How often do you change your bedding?
• How often do you eat in a restaurant?
• What is your biggest vice/guilty pleasure?

• Are you close to your family?
• Would you like to have children one day?
• What were your schooldays like?
• Can you swim?
• Do you celebrate Christmas?

• How do you celebrate Christmas?
• Have you ever met a celebrity?
• Do you use social media? If so, which platforms?
• Which phone app could you not live without?
• Do you prefer giving or receiving gifts?

• If you could afford to volunteer full-time for a charity, which would it be?
• Do you have a group of friends or individual friends?
• What’s your favorite season?
• What’s your favorite outfit at the moment?
• Do you wear jewelry?

• Tell me about your parents.
• What was your first ever job?
• Who is your favorite comedian?
• Do you like going to the cinema?
• Do you like the theatre?

• Who was your first kiss with?
• Do you have any siblings?
• Do you like walking?
• Who is your favorite Youtuber?
• Where do you sit to write your letters?

• Do you enjoy or dread weddings?
• Have you ever been a bridesmaid or a groomsman?
• Who is your celebrity crush?
• Can you sew?
• Are you any good at DIY?

• Do you exercise?
• Who taught you to cook?
• What’s your favorite sports team?
• Do you make New Year’s resolutions?
• If you had to talk for fifteen minutes about something, what would it be?

• What is something you wish you could change about the world?
• Favorite ice cream flavor?
• What was the last thing that made you laugh?
• What colors do you wear, mainly?
• Do you prefer writing things down digitally or on paper?

• What are a few things that remind you of your childhood?
• What stresses you out?
• Are you more of a girly-girl or a tomboy?
• What is your middle name?
• What are your favorite girl or boy names?

• What does your morning/evening routine look like?
• What’s something you’re oddly passionate about?
• Do you have any hidden talents?
• Which freaks you out the most: mice/rats, bugs, spiders, or snakes?
• What is your greatest fear?

• What is your favorite color scheme?
• How do you spend your free time?
• What are your thoughts on social media?
• Do you like wearing makeup?
• What makes you really sad?

• What do you daydream about?
• Are you an introvert or an extrovert?
• What are your thoughts on personality typing?
• What does eating healthy mean to you?
• What would be the tastiest meal, in your opinion?

• Have you broken any bones or gotten stitches?
• How tall are you?
• What was one of the scariest moments/days of your life?
• What was the highlight of your day?
• If you could travel anywhere for free, where would you go?

• What kind of car or truck do you want to get?
• What would your dream house look like?
• What “aesthetic” do you, love?
• What style of decor do you love? (i.e. farmhouse, modern, vintage, etc.)
• Are you a hugger?

• Do you play any instruments?
• How many siblings do you have?
• Do you have a big or small extended family?
• Does your family have any inside jokes?
• What is one thing you’re excited for and one thing you’re afraid of in the future?

• What are a few of your favorite movies?
• Does your family have any ____ traditions? (i. e. summer, Christmas, weekend, etc.)
• What are some of your favorite memories?
• What are a few of your favorite books?
• Do you prefer real books, e-books, or audiobooks?

• What is something you’re struggling with right now?
• What is something you’re super excited about right now?
• Do you like nicknames? Do you have any?
• Coffee, tea, or hot chocolate?
• Beach or mountains?

• One unpopular opinion you have?
• What do your vacations usually look like?
• Where have you traveled?
• How would your friends describe you?
• Where do you usually write letters?

• What is something you’re struggling with right now?
• What is something you’re super excited about right now?
• Do you like nicknames? Do you have any?
• Coffee, tea, or hot chocolate?
• Beach or mountains?

• One unpopular opinion you have?
• What do your vacations usually look like?
• Where have you traveled?
• How would your friends describe you?
• What do you think people’s first impression of you is?

• What is your favorite animal?
• What are your hobbies or interests? (i. e. reading, horseback riding, architecture, art, etc.)
• Do you have any pets?
• What do you think people’s first impression of you is?
• Do you put water on your toothbrush before or after the toothpaste?

• Do you like pineapple on pizza?
• What does your week normally look like?
• Do you live in the city, country, or somewhere in between?
• What are a few things you’re grateful for right now?
• What do you imagine your life will look like in ten years?

• Who are your role models?
• If you could meet with any person, past or present, who would it be?
• What is your favorite and least favorite thing about your appearance?
• What is your favorite and least favorite part of your character/personality?
• What would a perfect day look like to you?

• What is your favorite flower?
• Do you have a favorite number?
• Do you imagine shapes, numbers, and days of the week to have colors or personalities?
• What color is your hair? Your eyes?
• What is the view out the nearest window?

• If you could take any class you wanted, what would it be?
• What makes you cry?
• What makes you laugh?
• What is your favorite snack?
• When do you usually get up, and go to bed?

• How can I pray for you?
• When’s your birthday?
• How big is your family?
• What’s your astrological sign?
• What’s your dream job?

• How would you describe your fashion style?
• Do you wear makeup? Every day or rarely?
• Describe your hairstyle.
• Do you wear any type of glasses?
• Favorite school subject?

• Do you have a favorite candy bar?
• What’s your strongest childhood memory?
• What’s your dream travel destination?
• How many places have you been to?
• What’s your favorite local getaway spot?

• Do you prefer hotels or hostels?
• Have you ever flown first class?
• What funny memory do you have from your travels?
• How would you describe your travel style?
• What are your must-bring travel essentials?

• Are you a light or heavy packer?
• Do you like to cook new dishes or do you cook what you’re familiar with?
• What dish did you always eat as a child?
• What’s your favorite restaurant in your area?
• Are you a picky eater?

• What’s your favorite dish from X cuisine (i.e. Chinese, French, Italian, Mediterranean)?
• What is something you will absolutely not eat?
• What “quirky” food have you tried?
• Have you ever eaten any other animal meat apart from seafood, poultry, beef, or pork?
• What’s your go-to breakfast?

• Do you like brinner AKA breakfast for dinner?
• What’s your favorite pie flavor?
• Do you like pickled foods?
• Can you handle spicy foods? 
• If you had to pick one cuisine to eat for the rest of your life what would you choose?

• What is one cuisine or food you have always wanted to try?
• What’s your all-time favorite TV show that you can watch on repeat?
• Do you have a favorite Disney film?
• Are you a Star Wars or a Star Trek fan?
• Who’s your favorite Avenger?

• What are your thoughts on Gal Gadot as Wonder Woman?
• Do you have an all-time favorite Studio Ghibli film?
• What Youtuber do you not care to watch?
• What’s your current favorite Netflix series?
• Which Youtuber have you been watching the longest?

• What types of TV shows do you prefer to watch? 
• Do you like watching award shows?
• What TV show did you always watch with your family as a child?
• What anime show(s) do you like watching?
• Which actor/actress would you choose to play you in a biography?

• If you could write a movie script, what would the plot be about?
• Have you ever had any celebrity sightings before? 
• Would you rather see the future or travel back to the past?
• Would you rather have a photographic memory or be able to speak any and all languages in the world?
• If you could write a book about your life, what would the title of it be?

• What superpower would you want and why?
• If you could teleport, where would you teleport right now?
• What kind of old person do you think you’ll be?
• What fictional character do you think would be boring in real life?
• What do you love about yourself?

• Do you mind sharing an embarrassing story?
• Do you have any regrets?
• Are you more likely to avoid confrontation or face it?
• What do you look for in a significant other?
• What do you think is a waste of money?

• Do you trust your first impressions of people?
• What makes you feel better when you’re upset or angry?
• Who is in your family?
• What’s a fun fact about you that most people don’t know?
• What’s one thing you’re really good at?

• What is it like where you live?
• What’s something you like that most people dislike?
• What’s something you dislike that most people like?
• If you were granted three wishes, what would you wish for?
• If you were invisible for one day, what would you do?

• If you won the lottery, how would you spend the money?
• If you could relive any day of your life, which would you choose and why?
• Is there any song that instantly makes you happy?
• Do you have any birthmarks?
• When you were a child, what did you want to become when you grow up?

• What was your first pet and what was it called?
• Do you have any bad habits?
• If you were invisible for one day, what would you do?
• What has been your most memorable birthday so far, and why?
• What animal would you like to be reincarnated to? Why?

• Do you have any birthmarks?
• Do you have something that you can not live without?
• What is the first thing you do when you wake up in the morning?
• If you could invite 5 people to a dinner party, who would you invite, and why?
• What 3 items would you bring to a desert island?
• What movie have you watched more than 10 times?

• What would you put in a time capsule?
• Do you have a favorite quote?
• What is your favorite thing about your hometown?
• Do you know how to dance?
• Would you ever do a skydive?

• Do you like rides any roller coasters?
• Are you an early bird or a night owl?
• What is the last book you read?
• What is the best book you read?
• Do you have any tattoos or piercings?

• Do you have a top 5 travel bucket list?
• Do you like your name?
• Would you like to be famous someday?
• If you could have a mythical creature as a pet, what would it be?
• Which element best represents you?

• Is there anyone you want to be closer to?
• Do you like your cereal crunchy or soggy?
• What is your favorite scent?
• Do you prefer swimming in the ocean or pools?
• What would you do if you found $50 on the ground?

• What is one thing you would like to teach your children?
• If you could travel back to any era, which would you choose?
• What is your most used emoji?
• Favorite fairytale?
• Does your zodiac sign fit your personality?

• Favorite sea animal?
• A Disney princess you feel most relatable to?
• Favorite item in your room?
• What do you spend most of your money on?
• How did you get into pen paling?

• Do you believe in luck?
• Are you a competitive person?
• What was the best advice someone has ever given to you?
• Which social game was your favorite while growing up?
• Something that annoys you easily?

• Who is the person in the world that knows you best?
• Tell me one interesting thing about each person you live with.
• What is a weird habit that you have?
• If you could be any animal, what would it be and why?
• Do you have any scars? How did you get them?

• If you could only eat one food for a week, what would it be?
• If you could do anything you wanted for an entire day, what would you do?
• What’s the coolest place you have ever visited and why?
• Who is the person you most like to spend time with and why?
• What is the weirdest thing you posted on the internet?

Do you have some more great questions to ask your pen pal? Be sure to add them to the comments so we can add them o the list!

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