What is the most interesting question you can ask to get to know someone?
Last Updated: 16.06.2025 00:24
Will you kiss after your partner has gone down on you? Swallow or spit semen?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
51~ What tends to bring a smile to your face?
How far does good behavior take you in a prison?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
What topics are okay with you in comics and what topics should be totally off the table?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
How many partners have you had oral sex with? Who? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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How about if they talk dirty and/or call you names?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
How do I come out as queer to my best friend in a funny and stupid way?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
How can I handle my distrust and jealousy for my partner?
If YES, was it with 2 men or 2 women? Did you enjoy it?
If you say it, I will stop, and we can talk about it when you are ready.
34~ Do you like the lights on or off during sex?
Teens like me, what are your expectations when entering adulthood?
1- What was your first impression of me? Has it changed?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
39~ What are your love languages?
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80~ Share your top three fantasies/desires. (Be detailed) 😊
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…
9~ How many times over your lifetime do you think you have had sex so far?
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5- What do I do outside the bedroom that turns you on? How about, what turns you off?
22- Do you have any birth marks? How about scars? Care to share how you got them?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What's an uncomfortable truth you've learned to accept?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Why are Korean female leads so angry all the time?
7- What if a person smells a certain way? 8- How about smoking?
8- What are your thoughts on politics?
67~ Do you like it when your partner moans and/or is vocal during sex?
Why do old men think young women and girls would want them over guys their own age?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
7- What are your thoughts on religion? Is there an afterlife?
19~ Who/when was your first “heartbreak”?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
89~ Do you like taking showers together?
What is your view on sex? Meaning, When/Where/ How often/
25~ How do you feel about PDA? (Public Display of Affection)
How many times do you think you have “made love”?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
50~ How many children do you have? What are their ages?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
53~ How much can you tell me about the one thing you are most passionate about?
40~ What’s the weirdest place you’ve ever had sex?
19- Do/have you smoked? What do you prefer? How often?
28- What are some things that people do that irritate you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
30~ What's something unexpected that turns you on?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
33- If you could visit any time period, when would you pick? Please explain why?
48~ Have you ever paid or been paid for sex?
*** Deal Breaker Questions ***
*** Questions about Relationships/Past ***
10~ How many dates are necessary before you to have sex with someone?
76~ Have you had a threesome? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
83~ How do you feel about Porn?
18- How often do you drink alcohol? What is your favorite drink?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What was the longest? What was the shortest?
Model/Photographer Police/Criminal
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
38~ Share your most embarrassing sexual memory?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
3- What’s your favorite smell? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
I would allow you to do it… What would you do to me?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
44~ Care to share something about yourself that no one else knows about you?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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 like the “69” position? Do you prefer to be on top or bottom?
1~ How old were you when you had your first kiss? Who? Care to Share?
26~ What side of the bed do you sleep on?
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
6- Do you have dreams? Can you remember them? What do you usually dream about?
33- Beach or Mountains? Or is there another place to like better?
15- What's your favorite saying? What word or phrase is your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
47~ What would be your dream job and why?
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- How superstitious are you?
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
The Ice Breaker Questions
Family Relation Age Play
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
62~ Have you used adult toys?
17- What’s your favorite holiday? What’s your least favorite?
48~ Do you have any siblings? Are you close to your family?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
That one or two things that made you go hmmmm, OMG or wow!
Get this wrong and this could mean the end… :-) some funny, some not…
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
7~ How many times in one day have you had sex? Who/When/Where? 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?
What is your favorite position? Why?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
13- What is the craziest/scariest thing you've ever done?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
32- What's your greatest talent? Can I see it right now?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
What do you dislike about me? I asked you to be 100% honest.
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
2- What’s your favorite color? Do you a least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Escort/Client Job Applicant/Hiring Manager
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
3- What Superhero or Superpower would you want to be/have?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Would /have you ever given your partner a lap dance and Striptease?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
52~ Are you willing to make “those types” of bets with your partner?
11- How about if they like a certain sports team? 12-How about drinking too much?
9- What’s your favorite season and why? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Master/Slave Boss/Maid
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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,
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…
52~ What are your hobbies?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Over time has your thoughts on sex changed?
Would you allow me to clean every part of your body with my soapy hands and fingers?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
13- What’s your favorite drink? What’s your least favorite?
Do you watch it? What is your favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
* Give a rating for each one (0-100)
Any that are a turn off?
Prisoner/Prison Guard Landlord/Tenant
7-What do I do in bed that drives you wild? How about, what turns you off?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
*** Random Questions ***
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
84~ How do you feel about reading/listening to adult stories?
27- What was/ is nickname? Does it have a meaning behind it?
Would you read them together?
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?
23- What is your dream job? What was it as a child?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
If you win, what will you make them do?
Would you ever want to be woken up with oral and/or intercourse?
51~ Are you willing to play adult games with your partner?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
13- How about having a certain hair cut/style?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
If yes, what?
5~ When you first started having sex, was it what you thought it would be?
18~ Who/when was your first “crush”?
22- What is your favorite childhood memory? What is your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Nurse/Patient Celebrity/Fan
28~ What are some things that turn on? What is your biggest turn on?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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)
82~ Do you have any fantasies involving Role-Playing?
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?
49~ How many times have you been married? Why did they end?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
92~ Everyone needs a “safe” word. What is yours?
How old are you? Male or Female?
*** What’s Your Favorite…? ***
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
11- What's your favorite restaurant? What’s your least favorite?
Do you think this brought you closer together?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
36~ What is your favorite time of day to have sex/make love?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
15- What bad habit do you wish you could quit? Do you have any addictions?
Would you do it again, and would you rather 2 females or 2 males?
Have you ever? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What would you say to prove to yourself that it was really you?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
31- If given a chance to be immortal, would you take it? Why?
Teacher/Student Stranger/One Night Stand
Nothing too Serious
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
9- Is there something you’ve always wanted to ask me but you’re afraid?
Any that are a turn off?
70~ Would/do you have/like anal sex?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
92~ Have you ever had or have an STD? How many? What was it?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
65~ Describe the best orgasm you’ve ever had? Care to share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
You know that I will be 100% truthful, so ask.
14- What's your favorite dessert? Do you a least favorite?
21~ What was the best date you ever went on? What has been the worst?
How well do you know me? And some of your thoughts about me
12- What’s your favorite food? What’s your least favorite?
(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…)
11- List at least 5 things on your bucket list. Have you done any of them already?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
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?
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?
What have you learned about me that was new and/or surprising?
What is your favorite toy? Ever wanted to try a specific toy?
9- If you could have three wishes, what would they be? Why?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
1- What’s your favorite animal? Do you a least favorite?
10- What is your favorite family tradition? What’s your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
61~ How willing would you be to try new sexual positions?
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
8- What's your favorite flavor of ice cream? Do you a least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Do you like it when they show and tell you what they want?
Would you mind if your partner watched it? How about together vs alone?
42~ What’s your biggest regret in life?
17- Have you ever done drugs? Which ones? How often?
Do you have a favorite? Is it ok if your partner does?
19- What’s your favorite fairytale? What’s your least favorite?
Doctor/Nurse Stripper/Client
29~ What are some things that turn you off? What is your biggest turn off?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
4- For a pet, Cat, dog or other?
10- List 5 of your top pet peeves.
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
20- What’s your favorite candy? What’s your least favorite?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
37- Do you like your name? If you could change it, what would you change it too?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Does the thought excite you? Care to share?
Repairman/Lonely Wife Virgin/Experienced
15~ Have you ever been “in love”? Who? Care to Share?
Please share Did you stop?
What have you learned about yourself that you did not before this?
81~ Do you have any kinks and/or fetishes?
*** Questions About Me ***
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
71~ Would you give your partner a hand or foot job? Would you receive one?