What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 07:21
Prisoner/Prison Guard Landlord/Tenant
Does the thought excite you? Care to share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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What’s the longest time you gone without having sex, after, having it? How much time between the others?
28- What are some things that people do that irritate you?
How about if they talk dirty and/or call you names?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
*** Questions about Relationships/Past ***
My son got caught peeing on a carpet in his room and he is 12 years old. What should I do?
How old are you? Male or Female?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
31- If given a chance to be immortal, would you take it? Why?
What have you learned about me that was new and/or surprising?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Do you think this brought you closer together?
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78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
36~ What is your favorite time of day to have sex/make love?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
39~ What are your love languages?
How well do you know me? And some of your thoughts about me
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
10~ How many dates are necessary before you to have sex with someone?
33- Beach or Mountains? Or is there another place to like better?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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If NO, would you ever have one? Would it be with 2 men or 2 women?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
9~ How many times over your lifetime do you think you have had sex so far?
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What was the longest? What was the shortest?
Have you ever? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
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Do you have a favorite? Is it ok if your partner does?
89~ Do you like taking showers together?
Please share Did you stop?
What led Megan to marry into the Royal Family despite her successful acting career in Hollywood?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
29~ What are some things that turn you off? What is your biggest turn off?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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17- What’s your favorite holiday? What’s your least favorite?
* Give a rating for each one (0-100)
How many times do you think you have “made love”?
Why is my ex trying to provoke an argument with me?
19~ Who/when was your first “heartbreak”?
(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…)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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…
33- If you could visit any time period, when would you pick? Please explain why?
Model/Photographer Police/Criminal
52~ What are your hobbies?
Can you Deep Throat? Do you like the taste of yourself?
If you say it, I will stop, and we can talk about it when you are ready.
Get this wrong and this could mean the end… :-) some funny, some not…
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
13- What is the craziest/scariest thing you've ever done?
71~ Would you give your partner a hand or foot job? Would you receive one?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
7-What do I do in bed that drives you wild? How about, what turns you off?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
60~ How important is oral sex? Do you like receiving? Do you like giving?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
*** What’s Your Favorite…? ***
76~ Have you had a threesome? Care to Share?
What have you learned about yourself that you did not before this?
Do you like the “69” position? Do you prefer to be on top or bottom?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Would you allow me to clean every part of your body with my soapy hands and fingers?
6- Do you have dreams? Can you remember them? What do you usually dream about?
1- What was your first impression of me? Has it changed?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
23- What is your dream job? What was it as a child?
48~ Have you ever paid or been paid for sex?
Any that are a turn off?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
83~ How do you feel about Porn?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
40~ What’s the weirdest place you’ve ever had sex?
50~ How many children do you have? What are their ages?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
The Ice Breaker Questions
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
What do you dislike about me? I asked you to be 100% honest.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
15~ Have you ever been “in love”? Who? Care to Share?
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?
52~ Are you willing to make “those types” of bets with your partner?
61~ How willing would you be to try new sexual positions?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
*** Deal Breaker Questions ***
Would you read them together?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
11~ Have you ever been caught by your parents or children or others while having sex?
13- What’s your favorite drink? What’s your least favorite?
9- If you could have three wishes, what would they be? Why?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
You know that I will be 100% truthful, so ask.
If yes, what?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
9- What’s your favorite season and why? What’s your least favorite?
10- What is your favorite family tradition? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
*** Random Questions ***
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
How many partners have you had oral sex with? Who? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Nurse/Patient Celebrity/Fan
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Master/Slave Boss/Maid
8- What are your thoughts on politics?
22- What is your favorite childhood memory? What is your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Escort/Client Job Applicant/Hiring Manager
51~ What tends to bring a smile to your face?
19- Do/have you smoked? What do you prefer? How often?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
1- What’s your favorite animal? Do you a least favorite?
29- How superstitious are you?
92~ Everyone needs a “safe” word. What is yours?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Do you watch it? What is your favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
11- What's your favorite restaurant? What’s your least favorite?
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?
3- Should Pluto still be considered a planet? 4- How about smoking?
What would you say to prove to yourself that it was really you?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
17- Have you ever done drugs? Which ones? How often?
Doctor/Nurse Stripper/Client
32- What's your greatest talent? Can I see it right now?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
47~ What would be your dream job and why?
82~ Do you have any fantasies involving Role-Playing?
1~ How old were you when you had your first kiss? Who? Care to Share?
12- What is the weirdest thing you've ever eaten?
65~ Describe the best orgasm you’ve ever had? Care to share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
Would you do it again, and would you rather 2 females or 2 males?
62~ Have you used adult toys?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
13~ Is there a difference between, making love, having sex, and fucking?
48~ Do you have any siblings? Are you close to your family?
7- What are your thoughts on religion? Is there an afterlife?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
That one or two things that made you go hmmmm, OMG or wow!
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?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
10- List 5 of your top pet peeves.
Would you mind if your partner watched it? How about together vs alone?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
53~ How much can you tell me about the one thing you are most passionate about?
80~ Share your top three fantasies/desires. (Be detailed) 😊
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
7- What if a person smells a certain way? 8- How about smoking?
What is your view on sex? Meaning, When/Where/ How often/
44~ Care to share something about yourself that no one else knows about you?
13- How about having a certain hair cut/style?
18- How often do you drink alcohol? What is your favorite drink?
22- Do you have any birth marks? How about scars? Care to share how you got them?
If YES, was it with 2 men or 2 women? Did you enjoy it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
3- What’s your favorite smell? Do you a least favorite?
34~ Do you like the lights on or off during sex?
36- Do you play video games? What is your favorite? Do you a least favorite?
30~ What's something unexpected that turns you on?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Any that are a turn off?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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…
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?
Do you like it when they show and tell you what they want?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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,
34- Ever been to a concert? What was your favorite? Who would you like to see?
38~ Share your most embarrassing sexual memory?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
81~ Do you have any kinks and/or fetishes?
49~ How many times have you been married? Why did they end?
18~ Who/when was your first “crush”?
What is your favorite position? Why?
4- For a pet, Cat, dog or other?
Would you ever want to be woken up with oral and/or intercourse?
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)
51~ Are you willing to play adult games with your partner?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
42~ What’s your biggest regret in life?
67~ Do you like it when your partner moans and/or is vocal during sex?
3- What Superhero or Superpower would you want to be/have?
14- What's your favorite dessert? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Will you cheat again? How can, you be sure? Define what cheating is to you.
I would allow you to do it… What would you do to me?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** Questions About Me ***
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
15- What's your favorite saying? What word or phrase is your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
27- What was/ is nickname? Does it have a meaning behind it?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Teacher/Student Stranger/One Night Stand
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Family Relation Age Play
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
If you win, what will you make them do?
What is your favorite toy? Ever wanted to try a specific toy?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
19- What’s your favorite fairytale? What’s your least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
37- Do you like your name? If you could change it, what would you change it too?
5- Have you ever been hypnotized? Would you allow yourself to be?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
92~ Have you ever had or have an STD? How many? What was it?
12- What’s your favorite food? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
28~ What are some things that turn on? What is your biggest turn on?
84~ How do you feel about reading/listening to adult stories?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Over time has your thoughts on sex changed?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
2- What’s your favorite color? Do you a least favorite?
70~ Would/do you have/like anal sex?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
26~ What side of the bed do you sleep on?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
20- What’s your favorite candy? What’s your least favorite?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
15- What bad habit do you wish you could quit? Do you have any addictions?
45~ How do you feel about me blindfolding you? How about blindfolding me?
11- List at least 5 things on your bucket list. Have you done any of them already?
Nothing too Serious
Repairman/Lonely Wife Virgin/Experienced