What is the most interesting question you can ask to get to know someone?
08.06.2025 04:05
20- What’s your favorite candy? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
Doctor/Nurse Stripper/Client
How often do prisoners try to escape from jail/prison, and how many of them succeed?
What would you say to prove to yourself that it was really you?
19~ Who/when was your first “heartbreak”?
38~ Share your most embarrassing sexual memory?
Would you do it again, and would you rather 2 females or 2 males?
2~ How old were you when you got to 2nd base? (Tongue kissing, breast feeling, or outside the clothes genital contact) Who? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
How to protect yourself from wildfire smoke and poor air quality - The Washington Post
50~ How many children do you have? What are their ages?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Model/Photographer Police/Criminal
Xbox sale round-up June 3, 2025 - DLC - TrueAchievements
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Tomato Recall Escalates to Highest Health Risk Alert—Here’s What You Need to Know - Real Simple
I would allow you to do it… What would you do to me?
What was the longest? What was the shortest?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Why do you allow your cat to lie in bed with you?
34- Ever been to a concert? What was your favorite? Who would you like to see?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Why do older men like to get anal sex?
3- What’s your favorite smell? Do you a least favorite?
Any that are a turn off?
A comprehensive questionnaire, this should be a fun exercise to get to know each other. Try to give as much detail as possible when answering questions. You can go through this together and talk about each question or fill out the questionnaire as completely as you can and once you are done, go through each question together. If you have been together for a while, it is also fun to try to answer the questions for your partner. Remember this should be fun, so if you do not wish to answer a question you can “PASS” and not answer. Both should answer honestly and without judgement. (This is important, without judgement) I hope this helps you get closer and strengthens your relationship… You can learn a lot about the other person… and yourself…
What is the definite integral of x^x from 0 to 2?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
82~ Do you have any fantasies involving Role-Playing?
Would you ever want to be woken up with oral and/or intercourse?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Have you ever accidentally seen your mother-in-law doing something that was private to her?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
13- What is the craziest/scariest thing you've ever done?
Why are Trump supporters so incredibly stupid?
17- What’s your favorite holiday? What’s your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
*** What’s Your Favorite…? ***
25~ How do you feel about PDA? (Public Display of Affection)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Have you ever? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
49~ How many times have you been married? Why did they end?
How well do you know me? And some of your thoughts about me
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Do you have a favorite? Is it ok if your partner does?
What is your view on sex? Meaning, When/Where/ How often/
61~ How willing would you be to try new sexual positions?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
89~ Do you like taking showers together?
30~ What's something unexpected that turns you on?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
5- Have you ever been hypnotized? Would you allow yourself to be?
You know that I will be 100% truthful, so ask.
33- If you could visit any time period, when would you pick? Please explain why?
Will you cheat again? How can, you be sure? Define what cheating is to you.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
* Give a rating for each one (0-100)
Nothing too Serious
40~ If you could go back in time, and relive your life, with the knowledge you have now, what age would you go back to and why?
84~ How do you feel about reading/listening to adult stories?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What is your favorite position? Why?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
37- Do you like your name? If you could change it, what would you change it too?
11~ Have you ever been caught by your parents or children or others while having sex?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
11- List at least 5 things on your bucket list. Have you done any of them already?
7- What if a person smells a certain way? 8- How about smoking?
27- What was/ is nickname? Does it have a meaning behind it?
7- What are your thoughts on religion? Is there an afterlife?
92~ Everyone needs a “safe” word. What is yours?
Family Relation Age Play
What is your favorite toy? Ever wanted to try a specific toy?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
85~ If you gave me a “free Pass” to have me do anything for one hour, what would you want me to do to you?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
23~ What do you believe is required to have a successful and healthy relationship? (This is important, take your time, and really think about this)
5~ When you first started having sex, was it what you thought it would be?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How many times do you think you have “made love”?
*** Deal Breaker Questions ***
10~ How many dates are necessary before you to have sex with someone?
10- List 5 of your top pet peeves.
48~ Have you ever paid or been paid for sex?
1- What was your first impression of me? Has it changed?
Any that are a turn off?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
If yes, what?
These go from easy to answer, to OMG, you really want to know that?! to some serious thought. Take your time and have fun with this. The past is the past… it got you two here together…
51~ What tends to bring a smile to your face?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couples’ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETC…)
Nurse/Patient Celebrity/Fan
What do you dislike about me? I asked you to be 100% honest.
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
29- How superstitious are you?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
42~ What’s your biggest regret in life?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
59~ Have/do you masturbate? How often? What do you use? (Toys, Phone sex, Erotica, Hard Core, shower/water, etc) Would you, while your partner watches?
6- Do you have dreams? Can you remember them? What do you usually dream about?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
31- If given a chance to be immortal, would you take it? Why?
Prisoner/Prison Guard Landlord/Tenant
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
41~ What are you best at in bed? What do you think you are not so good at? Anything you want to get good at?
44~ Care to share something about yourself that no one else knows about you?
Can you Deep Throat? Do you like the taste of yourself?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
If you win, what will you make them do?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Does the thought excite you? Care to share?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
21- What's your favorite way to spend a weekend or time off?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Do you watch it? What is your favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
65~ Describe the best orgasm you’ve ever had? Care to share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
12- What’s your favorite food? What’s your least favorite?
81~ Do you have any kinks and/or fetishes?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
4- For a pet, Cat, dog or other?
How old are you? Male or Female?
Would you mind if your partner watched it? How about together vs alone?
17- Have you ever done drugs? Which ones? How often?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
12- What is the weirdest thing you've ever eaten?
13- How about having a certain hair cut/style?
If you say it, I will stop, and we can talk about it when you are ready.
Repairman/Lonely Wife Virgin/Experienced
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
52~ What are your hobbies?
47~ What would be your dream job and why?
9- If you could have three wishes, what would they be? Why?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
15- What's your favorite saying? What word or phrase is your least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
13- What’s your favorite drink? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
28~ What are some things that turn on? What is your biggest turn on?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
18~ Who/when was your first “crush”?
*** Questions about Relationships/Past ***
39~ What are your love languages?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
21~ What was the best date you ever went on? What has been the worst?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
83~ How do you feel about Porn?
11- Is there something you would like me to do, in any area of our relationship that I have not done, or you want more of?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Please share Did you stop?
9- What’s your favorite season and why? What’s your least favorite?
18- How often do you drink alcohol? What is your favorite drink?
3- What Superhero or Superpower would you want to be/have?
8- What are your thoughts on politics?
14- Do you have a “Deal Breaker”, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
70~ Would/do you have/like anal sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
26~ What side of the bed do you sleep on?
Master/Slave Boss/Maid
*** Questions About Me ***
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
52~ Are you willing to make “those types” of bets with your partner?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Escort/Client Job Applicant/Hiring Manager
That one or two things that made you go hmmmm, OMG or wow!
67~ Do you like it when your partner moans and/or is vocal during sex?
34~ Do you like the lights on or off during sex?
What have you learned about me that was new and/or surprising?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
51~ Are you willing to play adult games with your partner?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
36~ What is your favorite time of day to have sex/make love?
If NO, would you ever have one? Would it be with 2 men or 2 women?
22- What is your favorite childhood memory? What is your least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
33- Beach or Mountains? Or is there another place to like better?
32- What's your greatest talent? Can I see it right now?
Do you think this brought you closer together?
Would you read them together?
7-What do I do in bed that drives you wild? How about, what turns you off?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Do you like the “69” position? Do you prefer to be on top or bottom?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How many partners have you had oral sex with? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Get this wrong and this could mean the end… :-) some funny, some not…
23- What is your dream job? What was it as a child?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
15- What bad habit do you wish you could quit? Do you have any addictions?
*** Random Questions ***
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
85~ If I gave you a “Free Pass” for you to do anything to me for one hour, knowing that no matter what you did,
71~ Would you give your partner a hand or foot job? Would you receive one?
92~ Have you ever had or have an STD? How many? What was it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Over time has your thoughts on sex changed?
28- What are some things that people do that irritate you?
14- What is an embarrassing moment in your life? How about your most embarrassing?
How about if they talk dirty and/or call you names?
If YES, was it with 2 men or 2 women? Did you enjoy it?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Would /have you ever given your partner a lap dance and Striptease?
1~ How old were you when you had your first kiss? Who? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
62~ Have you used adult toys?
What have you learned about yourself that you did not before this?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Do you like it when they show and tell you what they want?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
50~ Where would you like to be touched more? Do you have a place that you want to be touched, that no one has, or has only happened a couple times? How about less?
10- What is your favorite family tradition? What’s your least favorite?
76~ Have you had a threesome? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
9~ How many times over your lifetime do you think you have had sex so far?
53~ How much can you tell me about the one thing you are most passionate about?
19- What’s your favorite fairytale? What’s your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
29~ What are some things that turn you off? What is your biggest turn off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
The Ice Breaker Questions
3- Should Pluto still be considered a planet? 4- How about smoking?
75~ If your partner wants an orgasm/have sex when you don't desire to have sex, how do you plan to deal with their needs?
80~ Share your top three fantasies/desires. (Be detailed) 😊
14- What's your favorite dessert? Do you a least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
2- What’s your favorite color? Do you a least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- Is there something you’ve always wanted to ask me but you’re afraid?
48~ Do you have any siblings? Are you close to your family?