Many inmates need housing when they come home. If you would be willing to help someone locate a residence upon exiting prison, please visit Inmate Housing Profiles.

Questions for pals.

68 posts / 0 new
Last post
fee's picture

MERRY CHRISTMAS now I bought this especially for you he says as he hands over a stun gun and pepper spray. blah!

blipsycat's picture

This is a really good idea for a thread. I've just starting writing to pen pals, and I'm not that good at coming up with things to talk about. So, all these questions will give me a lot of ideas of things I can ask them. Thanks to all who have contributed! :)

carlylou's picture

Yep go for it wofldreamer :o) Some of the old threads are the best and have alot of useful things on

carlylou's picture

Ok Carlylou I will paste them tomorrow I have been sick all this week and have not been able to do much.

i keep going back tp the first ones this is a good thread and soooo many questions !!!

KAM's picture

When is thanksgiving, forgive me its not a holdiay we celebrate here in the UK nor do we have cards specifically for it so I will have to get creative I guess..but the date would be useful please..

Thursday Nov. 24th.

Silas Sydenham
Silas Sydenham's picture

My thanksgiving is giving thanks that we don't have to worry about Thanksgiving in Australia. Now that the football finals are over, its just partypartyparty until February. All Saints' Day, Melbourne Cup, Schoollies' Week, Christmas, Hogmanay, Invasion Day. You just cannot get hold of a tradesman from November until March. And God only knows, I do try to get hold of those tradesmen.

FreakLikeMe's picture

Ok, please before anybody talks about Christmas.
Let us get over Thanksgiving Day. (The USA and Canada)
ones first.

Oh tell me about it.. I got 5 birthdays before i even think about Christmas.

actually 6..

FreakLikeMe's picture

i love silas, he's so funny:awe:

In an irritating kinda way.. he is lovely.

Melanie1972's picture

i love silas, he's so funny:awe:

Inna79's picture


Thank you very much for the posts and these amazing questions!!! I am going to use some of these questions right away!!!

OFF TOPIC: (What I am going to ask in a thread where can talk about this kind of questions)
I am new in here and just send letter and few postcards to pen pal and I am anxiously waiting his response. Sadly mail goes and (comes?) for about 4-7 days if I send it as a express mail (costs 11 euros) and otherwise 6-10 days + how long they handel it in VA, Greensville CC?! I live in Finland, europe.

Thank you for this forum and you people writing here, it's a big help for me and the others too I can guess.
I'm sorry if you find typos because english is not my native language...

wolfdreamer's picture

What was the happiest moment of your life? The saddest?
Who was the most important person in your life? Can you tell me about him or her?
Who has been the biggest influence on your life? What lessons did that person teach you?
Who has been the kindest to you in your life?
It’s been said that after they pass away, the most important people in our lives “live within us.” Is there anyone from your past that lives within you?
What are the most important lessons you’ve learned in life?
What is your earliest memory?
Are there any words of wisdom you’d like to pass along to me?
What are you proudest of in your life?
When in life have you felt most alone?
How has your life been different than what you’d imagined?
How would you like to be remembered?
Do you have any regrets?
What does your future hold?
Is there anything that you’ve never told me but want to tell me now?
Is there something about me that you’ve always wanted to know but have never asked?
Friends or Colleagues
If you could interview anyone from your life living or dead, but not a celebrity, who would it be and why?
What is your first memory of me?
Was there a time when you didn’t like me?
What makes us such good friends?
How would you describe me? How would you describe yourself?
Where will we be in 10 years? 20 years?
Do you think we’ll ever lose touch with each other?
Is there anything that you’ve always wanted to tell me but haven’t?
Where did you grow up?
What was your childhood like?
Who were your favorite relatives?
Do you remember any of the stories they used to tell you?
How did you and grandma/grandpa meet?
What was my mom/dad like growing up?
Do you remember any songs that you used to sing to her/him? Can you sing them now?
Was she/he well-behaved?
What is the worst thing she/he ever did?
What were your parents like?
What were your grandparents like?
How would you like to be remembered?
Are you proud of me?
Raising children
When did you first find out that you’d be a parent? How did you feel?
Can you describe the moment when you saw your child for the first time?
How has being a parent changed you?
What are your dreams for your children?
Do you remember when your last child left home for good?
Do you have any favorite stories about your kids?
Do you remember what was going through your head when you first saw me?
How did you choose my name?
What was I like as a baby? As a young child?
Do you remember any of the songs you used to sing to me? Can you sing them now?
What were my siblings like?
What were the hardest moments you had when I was growing up?
If you could do everything again, would you raise me differently?
What advice would you give me about raising my own kids?
What are your dreams for me?
How did you meet mom/dad?
Are you proud of me?
Growing up
When and where were you born?
Where did you grow up?
What was it like?
Who were your parents?
What were your parents like?
How was your relationship with your parents?
Did you get into trouble? What was the worst thing you did?
Do you have any siblings? What were they like growing up?
What did you look like?
How would you describe yourself as a child? Were you happy?
What is your best memory of childhood? Worst?
Did you have a nickname? How’d you get it?
Who were your best friends? What were they like?
How would you describe a perfect day when you were young?
What did you think your life would be like when you were older?
Do you have any favorite stories from your childhood?
Did you enjoy school?
What kind of student were you?
What would you do for fun?
How would your classmates remember you?
Are you still friends with anyone from that time in your life?
What are your best memories of grade school/high school/college/graduate school? Worst memories?
Was there a teacher or teachers who had a particularly strong influence on your life? Tell me about them.
Do you have any favorite stories from school?
Love & Relationships
Do you have a love of your life?
When did you first fall in love?
Can you tell me about your first kiss?
What was your first serious relationship?
Do you believe in love at first sight?
Do you ever think about previous lovers?
What lessons have you learned from your relationships?
Marriage & Partnerships
How did you meet your husband/wife?
How did you know he/she was “the one”?
How did you propose?
What were the best times? The most difficult times?
Did you ever think of getting divorced?
Did you ever get divorced? Can you tell me about it?
What advice do you have for young couples?
Do you have any favorite stories from your marriage or about your husband/wife?
What do you do for a living?
Tell me about how you got into your line of work.
Do you like your job?
What did you think you were going to be when you grew up?
What did you want to be when you grew up?
What lessons has your work life taught you?
If you could do anything now, what would you do? Why?
Do you plan on retiring? If so, when? How do you feel about it?
Do you have any favorite stories from your work life?
Can you tell me about your religious beliefs/spiritual beliefs? What is your religion?
Have you experienced any miracles?
What was the most profound spiritual moment of your life?
Do you believe in God?
Do you believe in the after-life? What do you think it will be like?
When you meet God, what do you want to say to Him?
Serious Illness
Can you tell me about your illness?
Do you think about dying? Are you scared?
How do you imagine your death?
Do you believe in an after-life?
Do you regret anything?
Do you look at your life differently now than before you were diagnosed?
Do you have any last wishes?
If you were to give advice to me or my children, or even children to come in our family, what would it be?
What have you learned from life? The most important things?
Has this illness changed you? What have you learned?
How do you want to be remembered?
Family heritage
What is your ethnic background?
Where is your mom’s family from? Where is your dad’s family from?
Have you ever been there? What was that experience like?
What traditions have been passed down in your family?
Who were your favorite relatives?
Do you remember any of the stories they used to tell you?
What are the classic family stories? Jokes? Songs?
Were you in the military?
Did you go to war? What was it like?
How did war change you?
During your service, can you recall times when you were afraid?
What are your strongest memories from your time in the military?
What lessons did you learn from this time in your life?
Remembering a loved one
What was your relationship to _____?
Tell me about _____.
What is your first memory of _____?
What is your best memory of _____?
What is your most vivid memory of _____?
What did _____ mean to you?
Are you comfortable/ can you talk about _____’s death? How did _____ die?
What has been the hardest thing about losing _____?
What would you ask _____ if _____ were here today?
What do you miss most about _____?
How do you think _____ would want to be remembered?
Can you talk about the biggest obstacles _____ overcame in life?
Was there anything you and _____ disagreed about, fought over, or experienced some conflict around?
What about _____ makes you smile?
What was your relationship like?
What did _____ look like?
Did you have any favorite jokes _____ used to tell?
Do you have any stories you want to share about _____?
What were _____’s hopes and dreams for the future?
Is there something about _____ that you think no one else knows?
How are you different now than you were before you lost _____?
What is the image of _____ that persists?
Do you have any traditions to honor _____?
What has helped you the most in your grief?
What are the hardest times?

wolfdreamer's picture

1. What was your favorite Halloween costume and why?

2. If you could have dinner with any three people from any time, fictional or non-fictional, who would they be and why?

3. If you could be invisible, where would you go and what would you do?

4. If your life was turned into a movie, what actor would play you?

5. What made you laugh the hardest in your entire life?

6. What's your favorite childhood memory?

7. If you were a waiter and a customer was being rude, would you spit in their food?

21 Questions to Ask a Guy - More Intimate Questions

Some questions to ask once you know a guy a bit better.

8. What is your deepest regret?

9. Have you ever dated someone from another race? Would you?

10. What was your first date like?

11. What's the worst lie you ever told? Did you get caught?

12. If you suddenly found yourself turned into a woman, how would you spend your day?

13. How do you handle people you don't like?

14. Would you rather be smart and ugly or dumb and beautiful?

21 Questions to Ask a Guy - Sexually Intimate Questions

Lay these questions on a guy when you know him well.

15. Do you have a sexual fantasy no one else knows about?

16. What's the difference between sex and making love?

17. If you could change the age at which you lost your virginity, would you? Would it be younger or older and why?

18. What's the craziest place you ever had sex?

19. Have you ever had sex with someone when you didn't really want to?

20. What turns you on? Turns you off?

21. Have you ever cheated on your partner? Did this person ever find out, and if so, what happened?

wolfdreamer's picture

1. What's the hardest thing you've ever done?

This random question reveals a lot about a guy. Both the answer and how he answers are revealing. Does he try a joke? Something like "Asking you out." Or does he answer the question seriously? "Getting over the death of a loved one." Either way you learn a lot.

2. If you were a car, what kind of car would you be?

Does he see himself as a fast sports car, an old classic pick up or a sturdy SUV? This random question can be fun.

3. If you were a city, what would you be?

This random question looks into a few aspects of a guy. Is he L.A. glitz? New York energy? Romantic Paris? Ancient Rome? Or small town USA?

4. If you were a movie, what would you be?

Would he be an action picture? A porn? A romantic comedy? Science-fiction? You can follow this up with, what actor would play you in the movie?

5. If you were a soup, what would you be?

I know. This one may sound kind of out there - but that's the point. Here you're looking at a guy's imagination and sense of humor. Will he go with the flow and answer the question or will he think it's weird? Either way, this random question reveals a guy's personality. Is he chicken noodle? Beef stew? Thick and chunky? Lentil? This one's mostly for fun.

6. If you were a tree, what would be carved in your trunk?

Another question that sounds kind of out there, but what did you expect - these are supposed to be random!

7. If you were sand, what would you say to people on your beach?

Have fun? Don't pollute? Use sunscreen! This is a chance for a guy to get creative and use his sense of humor.

8. If you were a house, what would you say to the people living inside you?

This random question is a bit more complicated than the one's before it, gauging humor, imagination and a guy's sense of home.

9. If you were a pebble, what would you say to a little kid throwing you into a pond?

Another opportunity for a fun question to get a random conversation going.

10. If you were an animal, what would you be?

This one's pretty easy for a guy. Just pick a cool animal and call it a day. The real key is the explanation. Be sure to ask the follow-up question: Why'd you pick that animal? Chances are he wouldn't have answered the question without already thinking of his explanation, which is what you're looking for with this one.

11. If you could travel through time and meet yourself when you were a kid, what would you say?

This random question deals with a number of issues. If a guy is money-oriented, he might say "I'd tell myself to buy Microsoft stock." Or he might do the whole "Back to the Future" sporting bets thing. This question deals with regrets and opportunities.

12. If a bartender named a drink after you, what would it be called? What would be in it?

This is another creativity and imagination kind of question that also looks into drinking patterns.

13. If you had to eliminate one thing in your life, what would it be?

A variation of the "If you were stranded on a desert island..." kind of questions.

14. If your house was on fire and you could only save one thing, what would it be?

Let him know that all his pets and loved ones are not in the house. Here you're looking at what material things a guy finds important.

15. What did you want to be when you were little and are you that now?

A little more roundabout way of asking about a guy's job and his attitude toward it.

16. If you could be any cartoon character, who would you be?

Would he be one of the Superfriends? Papa Smurf? Spongebob? Charlie Brown?

17. What do women like about you the most? The least?

This random question looks at how he thinks the opposite sex perceives him. On another level it also examines how he sees himself.

18. Should the guy always pay for a date?

This can be a hard question for a guy to answer . There's no clear-cut right or wrong response.

19. What would be the title of your autobiography?

Another random question more for fun. But then if his title is "No Regrets" or "Positive Impact" these are vastly different than "A Wasted Life."

20. If you had one superhero ability, what would it be?

This random question is mostly for fun but can be revealing. For example, the ability to fly is vastly different from the ability to see through anything but lead.

One thing to keep in mind is the old saying "Every question contains a power not found in the answer." What that means is simply - you can tell a lot about a guy by the questions he asks.

Remember the trick with many of these random questions lies in the answers. If a guy is into you, he may try to give you the answer he thinks you want to hear. That's easy to do with regular questions, but with more random questions, it's harder for a guy to figure out what answer you want, which makes them more revealing. Also remember that what is most revealing may not be the actual answer, but how he answers.

[="silver"]- - - Updated - - -[/]

Where do you see yourself professionally five years from now?
What is your job profile all about?
So, what are your hobbies?
What are you on the lookout for in a relationship?
If you had three wishes, what would they be?
What is the one thing you love about yourself?
Which is your favorite sports and sports person?
What kind of music do you love to listen to?
Describe yourself in five words.
So, what are your ideas about having fun?
Would you kiss a girl on the first date?
How important is sexual compatibility according to you?
If you were given an entire day off with your date, how would you spend your time?
Tell me about your favorite movie.
How long have you been speed dating?
What according to you is your most prized possession?
Which is the best book you have read so far?
Can you define love in your own way?
Have you been in a relationship before, and if so, why did you break up?
Who is your favorite celebrity or Hollywood actress and why?
What would you like to change about yourself?
How would you like to spend a Sunday morning?
How much importance do you attach to religion?
Have you ever felt the need to get married?
What qualities are you looking for in a girlfriend?
What do you find the most attractive in the opposite sex
What are your hobbies?
Would you forgive your partner if they cheated on you?
What kind of music do you like?
Funny Questions (no date guaranteed!)
Would you mind if my mom joined us on a date as well?
Are you the same guy I met aboard the Star Trek?
Can I leave right now? My dog must be missing me!
Have you been arrested for crime?
How would your best friend describe you?
If you could live anywhere in the world, which place would you choose?
What is the one thing in the world that makes you cry?
Is the cup half empty or half full?
Do you know any tricks?
Which animals represents you the closest?

wolfdreamer's picture

If you were an animal, what would you be and why?
If you were a cartoon, which one would you prefer being?
What is the weirdest thing you have ever eaten?
What's the worst thing you did as a kid?
What do you do to have fun?
Have you been told, you look like someone famous? (This question looks simple but some really funny answers can come up!)
What is that one thing which makes you different?
If you were the Miss World, what would your message for aspiring models be?
If you were to name one piece of clothing that describes you, what would you say?
If you could eliminate one thing from your daily schedule, what would it be and why?
If you wake up as (name any famous personality), what's the first thing you would do?
Name one funny trait you have, that you would like others to know.
Which letter of the alphabet describes you best? (Interesting, isn't it?)
If you turn into your partner for a day, what would you do?
What's the funniest pick up line used on you?
Share one truth and one lie about your personality and let the others guess which is what.
If you were to write a book about yourself, what would you name it?
Which body part would you choose to get a tattoo done?
If you were to get a permanent tattoo done, what would it be and where?
Name one thing that's impossible to do for everyone present here.
Tea or coffee? Earth or Mars? Crayon or paintbrush? Candy or ice cream? Famous Five or Secret Seven? (You can add as many pairs as you can think of and make it a rapid-fire kind of an icebreaker questionnaire.)
Tell us something you hate doing. Why?
What's your pet peeve?
Have you even been in jail?
Were you ever drunk?
Name one thing that drives you crazy.
What's the one thing, you can't live without?
As a child, what did you wish to become when you grew up? (A good conversation starter indeed!)
What's your motto in life? (Now this one's an icebreaker question to get to know someone.)
Share a funny incident in your life.
If you could have an unlimited storage of one thing, what would it be?
What's the funniest prank ever played on you?
What's the naughtiest thing you have done in school?
If given a chance, who would you like to be for a day? Or who would you like to exchange roles with?
What's the funniest daily horoscope you have read?
What's the silliest thing you have heard people say about you?
Share one funniest, one silliest and one wackiest status you have put up on a social networking site.
Would you rather be a giant rodent or a tiny elephant? (Here are some more would you rather questions you may choose from.)

wolfdreamer's picture

Describe your self. What do you think about yourself and do you think people perceive you in the same way?
Which is your most favorite book ever?
Which is the one television character that you simply adore?
What kind of music do you like?
Which is your favorite genre of movies? (Comedy/Romance/Suspense/Action/Horror)
What do you do when you feel very sad or depressed?
What makes you angry? Are you short-tempered? How do you overcome your anger?
Which is the best vacation you've ever had?
If you could have a luncheon with any three people (real or fictitious/from any time period/dead or alive), which three people would you choose and why?
Which is your most cherished childhood memory? What kind of kid were you, naughty or nice?
If given complete freedom to start afresh, what profession would you choose and why?
What is your idea of fun? If given a chance to skip work for a day, how would you spend the entire day?
Which is your favorite time of the day?
Are you a morning person or a night person?
What is the craziest thing you've ever done?
Name one person you love the most and one person you hate the most.
If we were a couple and we had a fight, how would you try to patch things up?
What is the funniest prank played on you or played by you?
If given a choice, which animal would you want to be? Why?
Who was your first crush? Did you ever tell him/her about your feelings?
Which is your most favorite place in this earth?
If you were stranded on a lonely beach, what are the five things that you would want to survive?

debbiety's picture

It's all good Gemma I have asked the same questions 4 or 5 times myself but its always fun lol

personwithaname's picture

What nationality are you? Asian

What’s your shoe size? 6.5

What’s your favorite food? anything good? I was on a sashimi kick for awhile but rn im craving salads and like soup? idk im cold

What’s your favorite candy? gum its not candy but it comes in diff flavors

What’s your favorite TV show? bobs burgers, im currently in love w it and i keep rewatching eps so thts how u know its real

What are your favorite movies? eternal sunshine of the spotless mind, call me by your name

Who’s your favorite actor or actress? emma stone i love her shes so adorable and she makes great facial expressions

What’s your favorite cartoon? bobs burgers bb or steven universe

What’s your favorite kind of music? rock , pop , indie, recently ive been getting into edm though

What’s your favorite song? rn ive been listening to harry styles sing lizzos song juice, its so good but rlly only the ending though haha

What’s your favorite color? periwinkle

What’s your favorite pastime? idk what tht means i guess reading n listening to music

What’s your favorite book? elena vanishing

What’s your favorite quote? "we accept the love we think we deserve"

What’s your favorite phrase? go git em brotha (its not my favorite phrase what am i saying ahh but its a good one that can be used in a variety of circumstances)

What’s your favorite word? oy vey (tht may b two words but dont rag on me 4 tht)

What is your favorite flower? dahlia / forgetmenots / bbys breath

What’s your favorite flavor of ice cream? mint chocolate chip

What’s your favorite sport? soccer / badminton / ping pong

What’s your favorite day of the week? saturday it just seems like a nice flowing word ya know

What is your favorite restaurant? i dont have one i like food n i like to eat it n thts about it

What is your favorite drink? milk, i ate expired dairy recently and tht was NOT fun i do not recommend

If you were standing on a corner in Winslow, Arizona, what would be on your mind? where is tht. Id be like what do i do now. im at a corner where should i go next

If you could eat lunch with one famous person, who would it be? steve jobs? just someone w good insight and can help me better myself as a person

If you won the lottery, how long would you wait to tell people? i wouldnt except 4 myself i dont want their opinions to change and i know they can use it as a manipulative vice

Can you juggle? rlly badly but sure

What did you have for breakfast this morning? a bowl w eggs steak potatoes cheese and pepper

What’s the last movie you saw in theaters? i dont watch a lot of movies so idk 

What one person would you never want to meet? someone tht  wants to hurt me and in a way tht i cant deflect it or do other things that i do not want

How do you know when a Smurf suffocates? you see them balloon a lil like violet from the charlie and the chocolate factory

Have you ever been in a car accident? no i think, a car hit us once but nothing bad happened so

How many times did you fail your driver’s test? i passed it bbbbyy

Which store would you choose to max out your credit card? a store that has good resale value on its items

What’s the most annoying thing people ask you? is tht rlly ur name

What time did you wake up this morning? 200 pm

When’s your bedtime? idk 

When’s the last time you cried? last night when i got charged for stuff tht i unsubscribed too i was so mad

Do you have any piercings and where? ears only but i want belly button ones idk

Do you have any tattoos and where? arm, ankle, hand, elbow, knee, thigh

How many candles were on your last birthday cake? i didnt have candles i dont remeber my bday tbh

Before this, who was your last letter from? idk these are some hard questions to answer

Who are you most like in your family? myself , nah jk my mom 

What’s your best feature? my lips or cheekbone or eyebrows

What’s your worst feature? my nose my eyes

Have you ever had an imaginary friend? yea its a lot of work to maintain a stable image in ur mind cause i always wanna b switchin it up

What personality traits do you hate most in other people? when theyre goofy and act stupid and unconfident 

Is your middle finger longer than your ring finger? yes

Are you afraid of the dark? sometimes

What’s your biggest pet peeve? me not getting my way but thats called being stupid and thats sometimes who i am

What do you like most about the opposite sex? their energy 

What do you dislike most about the opposite
sex? um im shy sometimes so ig they intimidate me but thts lame i feel like

Would you date someone who was missing teeth? idk if they had fake teeth to cover it

What was your most embarrassing moment? i have too many 

What’s the best way to spend the afternoon? w friends or exploring and being by myself

Gold or Silver? gold if u wanna be girly, silver if u wanna b badass

Who would you hate to be stuck in a room with? someone gross and boring or annoying 

What inspires you? people and their thought processes

Would you prefer living at the beach, in the city, or in the country? city i dont wanna b bored

Popcorn: Butter, Air, Salted, Caramel or all? salted w butter or kettle corn style tht shit slaps

Favorite Sandwich filling? tomatoes? cheese? mustard

What characteristics in people do you despise? laziness / unwilling to cooperate

How many keys on your key ring? 0

Where would you retire? somewhere fun

Red or White Wine? red

What did you do for your last birthday? hung out w a friend of mine

Do you carry an organ donor card? no

Where do they have the best pizza? carmines

Where's the best place to meet a guy or girl? in person , at school, or i guess kroger idk

Magicians: cool or creepy? cool

Do you chew gum? yes

What are your favorite magazines? people , whatever has interesting gossip

Do you floss everyday? no 

Which character on Friends has the personality closest to yours? um i hope chandler i think i have jokes but not all of them stick the landing

What time is it? 540 am

Do you have any pets? i used to have fish

Have you ever been toilet papering(Halloween tradition)? no 

Have you ever loved someone so much it made you cry? yes

Croutons or bacon bits? bacon ?

Disney or Warner Bros.? disney i dont remeber what warner does

Favorite fast food restaurant? chick fil a 

Last person you went out to dinner with? my friend 

Ford or Chevy? neither

If you were sent to an abandoned island, what are the 5 things you'd take with you? Boat is not an option. whatever is needed to survive a resort, and airplane

If you had a theme song, which one would it be? here i am once again

If you had a crystal ball to answer any one burning question, what question would you ask? whos my love or whats my purpose

If you had the power to change the world, what one thing would you change? ig evil? make ppl a little better

What famous person (living or dead) would you most like to have dinner with? Why? the arctic monkeys

"If you had only 24 hours to live, you had no restrictions, money was not an object, so you could do whatever you wanted with who ever you wanted, what would you do?"

What do you want most right now? go to thailand and get tats 

What are you most grateful for? my family

What is the best thing about your youth? time

What is the worst? pressure

When have you felt most uncomfortable being nude? when taking nudes

In what way are you least understood? emotionally or mentally

What was the worst vacation you ever took? to a city nearby

What would you most readily die for? my parents maybe

What would you most like sympathy for? nothing

What is your favorite store in the world? anthropologie

What was your most disappointing sexual experience? oof too many ah boys suck

What is the strongest opinion you hold? idk

What is the most difficult problem you’ve 
ever had to solve? i dont know i solved it so who cares

What is the best example of “perfection” you can think of? 

Who is the person you miss the most right now?

Where would you most like to be right now?

What was the biggest sin ever committed against you?

What sin do you most enjoy committing?

What is the one thing you’d most like to be forgiven for?

Who is the person you know with the purest soul?

Who is the person most loyal to you?

What is the greatest thing you’d sacrifice to find true love?

Who made the strongest first impression on you?

What is the biggest injustice you have ever suffered?

What single word best describes you?

What single word do you hate most?

What is the most surprising action you’ve
ever taken?

When was your life most out of control?

Who is the person most similar to yourself in the world?

Who is the person most able to make you laugh?

What is the most valuable thing you own?

What person have you taken most advantage of?

What subject would you most like to learn
more about?

Who in life have you felt the strongest need to protect?

What would you most like to be remembered for after you die?

Whose smile can most easily persuade or seduce you?

What is the hardest thing about love?

What is the cruelest thing a person has ever said to you?

What is a recurring dream that you most enjoy?

With whom is your willpower weakest?

What are the best and worst letters you have ever received in the mail?

What is the sexiest thing anyone has ever worn for you?

What crime have you been most tempted to commit?

What is the worst crime you have ever committed?

What would be the best way to get rid of a dead body?

What crime from history fascinates you the most?

What is the worst punishment you’ve ever had to endure?

Who do you think was the worst criminal in history?

What’s the weakest you’ve ever been?

Who had the best body you ever made love with?

When do you most need attention from your lover?

Who is the dumbest person you’ve ever dated more than once?

What in the world would you most like to see protected?

Where would you most hate to be pierced?

Who is the person you’d most like to take revenge on?

Who is the most sensitive person to your needs?

What is the most difficult confession you’ve ever had to make?

What is the most painful thing a lover has ever done to you?

Who most deserves your love?

What is the hardest thing to forgive?

Who was the least attractive person you were attracted to?

What was your most difficult break up?

What’s the thing you know most about?

Who have you been most frustrated by in your life?

What is the best thing you’ve ever put in your mouth first thing in the morning?

What was the most difficult choice you were ever forced to make?

What is the single nastiest thing you’ve ever done to someone?

What is the cruelest thing you’ve ever suffered?

What is the best thing you’ve ever tasted?

What thing about your family are you least proud of?

What topic do you feel uncomfortable discussing with your lovers?

What kind of power do you want most?

What is the best gift you ever gave to someone?

What is the hardest decision you ever had to make?

What is the thing of the highest value you have ever lost?

What is the most painful thing you’ve ever had to tell a friend?

What is the biggest favor a friend has ever done for you?

What is the cruelest thing you have ever done to a friend?

What is the thing a friend has that you would most like to have yourself?

What is the strongest craving you get?

What is the best toy you have ever owned?

When in your life have you felt the loneliest?

What is your strongest emotion?

What’s the best way to commit suicide?

When were you most disappointed in yourself?

What’s the shortest amount of time between orgasms you’ve ever experienced?

Which law would you most like to change?

Who is the person you have hated the most in your lifetime?

What has disappointed you the most?

What is the oldest you’d like to live to?

What’s the best year of your life so far?

What’s the shortest time you’ve spent between meeting someone and having sex?

What is the best position for sex?

What’s the best compliment you’ve ever received?

What’s the easiest money you have ever earned?

What’s the worst thing you have done on account of money?

What would you find hardest about being in prison?

Who is the person with whom you’ve been most infatuated with?

What is the one thing you are proudest of in life?

What one thing would you most like to happen tomorrow?

What is the most indulgent thing you do each day or week?

What is the worst sexual experience you ever had?

What one thing would you most like to steal?

What is the biggest thing you have ever stolen?

Which sibling is or was most favored by your parents?

What is the worst emotional pain you’ve ever suffered?

Whose thoughts would you most like to read?

Who is the person you know who you’d most like to see naked?

What has truly been the most embarrassing moment of your life?

Who is the person you’d most like to torture?

What is the biggest risk you’ve ever taken?

What have you lost that you’d most like to retrieve?

Who is the person you’d like to help most?

What is the worst thing you have ever said to your mother?

What is the closest you’ve ever come to death?

What is the biggest surprise you’ve ever had in bed?

What is the worst physical harm you have ever inflicted on someone?

What is the most erotic scent you have ever smelled?

What is the most disgusting thing you’ve ever had to do?

When do you have the most difficult time telling the truth?

In which year of your life did you change the most?

Who is the person you most wanted to have an affair with but didn’t?

Who is the person you’d most like to touch but never have?

What is the best thing you have ever gotten for free?

What is the wildest thing you’ve ever done in public?

What do you least respect about your father?

What is the thing your best at?

What dream are you least likely to ever forget?

What is the most original thing your lover has ever done?

What is the most daring sexual thing you’ve ever done with someone of the gender you don’t prefer sexually?

Who is the one person you have learned the most from in life?

What is the worst thing you have to do each morning?

What do you have the worst reputation for? And the best?

What is the least amount of money you’d accept to never have sex again?

What is the longest amount of time you could spend on a desert island with your lover or spouse before needing the company of others?

Who is the person you most regret having sex with?

What is the most erotic moment in your life so far?

What is the youngest age at which people should begin having sex?

What is the longest you have gone without having sex?

What is the single most bizarre place you’ve ever had sex?

Who is the person you can most easily anger?

Who was the best lover you ever had?

Who is the person you are most open with?

What is the most amount of money you would spend for proof if you suspected that your spouse was cheating on you?

Who is the person you find hardest to please?

What is the one thing you miss most about another place?

Who taught you the most about good sex?

What was the hardest secret you ever had to keep?

What is the most sacred thing in your life?

What is the biggest lie you’ve ever been told?

What is the grandest lie you’ve ever told?

What was the hardest apology you ever delivered?

What do you feel most guilt for in life?

What is the one thing you’d most like to forget?

What is the single thing in your life you are least likely to ever forget?

What is the most comforting thing you have in your home?

What is the biggest myth about sex?

What is the largest sacrifice you ever made?

Who is the easiest person to be with that you know?

What is the biggest regret of your life so far?

Who is the worst enemy you ever made?

What is the one thing in life you care about most?

What is the one thing that gives you most joy in the world?

What do you most look forward to? And dread?

What was the biggest thing you ever got away with?

When were you happiest to come home?

What is the worst trouble you have ever gotten yourself into?

Who is your greatest hero from history?

What is the best telephone call you’ve ever received or made?

What’s the best thing you ever found?

What was the most jealous moment of your life?

Where in the world have you felt safest? And most in danger?

When did you have the most fun in your life?

Who is the person you make feel guilty most often?

What’s the single most beautiful sight you’ve ever seen?

Which nationality do you find best looking overall?

What one part of your body do you think comes closest to being ideal?

When have you found it hardest to look at yourself in the mirror?

What’s the most extreme thing you would do to your own appearance to make yourself look

What’s the best hiding place you know?

What is the best gift you ever received?

Whose absence have you felt most in your life?

What was the best wish you ever had come true?

What was the moment in your life you felt most in love?

What is the worst way you abuse your body?

Who have you most feared in your life?

What is the best thing to do right after sex?

In what situation do you have least control of your emotions?

What is your best memory from your child hood?

What would you most like to hear from your father?

To whom do you talk most about sex?

What is the one thing that most pleases you?

What news do you most fear hearing?

What is your worst addiction?

What’s the biggest advantage you have going for you?

What do you most want to change in your life?

What do you most need to change in your life?

What is the best thing about your life?

What was the worst accident you ever experienced?

What habit would you most like to give up?

In what situation do you most rely on your parents?

In what area of your life are you neediest?

What questions do you avoid most?

What would you most like to stop?

How do you flirt best?

What would you like to change most about women?

What is the best thing about being a man/woman?

What is the biggest mistake you’ve ever made in a relationship?

What is the quality you love most in your partner?

What is the biggest advantage you have over your lover?

What is the single best thing you’ve done for your lover?

What is the most difficult thing about being married?

What do you brag about most when trying to impress your lover?

What would you least be able to forgive in your spouse?

Who is the closest thing to a sex addict you’ve ever known?

What makes you most nervous?

What are you most greedy for?

What makes you lose your temper most easily?

What part of the female body fascinates you most?

What is the wildest thing you’ve ever done in a car?

What is the worst word anyone ever used to describe you?

What would you most like to change in your house?

What is the strongest drug you have ever tried?

What makes you most content?

What is the best game that you play?

What’s the worst revenge you’ve ever had to suffer?

What’s the best revenge you’ve ever taken on someone?

What is the biggest favor you’ve ever done for a friend?

What is the worst habit you’ve ever had?

What was the worst experience you ever had involving alcohol?

What’s the deepest depression you’ve ever been in?

What’s the lowest thing you’ve ever done?

What’s the highest price you would pay for
great sex?

What’s the most romantic evening you’ve ever had?

What was the worst year of your life?

When were you most disappointed by a friend?

What is the most annoying habit your lover has? And how do you most annoy him/her?

What was the hardest you ever fought for something?

What was the weakest excuse you ever used?

What is the greatest sacrifice anyone has ever made for you?

What has been the single most important influence on your life?

What is the most worthy cause on Earth?

What is the hardest test you’ve ever taken?

What was the most difficult promise you’ve ever had to keep?

In what situation would you most enjoy being temporarily invisible?

What would be the quickest way to hell for you?

Who is the most amazing relative in your family?

What is the emptiest part of your life?

What was the hardest question you’ve ever answered?

What would you most easily be driven to kill for?

What’s the biggest surprise you’ve ever had?

What’s the biggest failure of your life so far?

What is the thing you’d most like to begin?

What is the thing you’d most like to complete?

What was the greatest number of times you had sex in one day?

What is the best place to touch, and to be touched?

When did it take you the longest time to reach orgasm?

What’s the most physical demanding sexual position you’ve ever tried?

What was your quickest quickie?

Who was the noisiest partner you ever made love with?