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