What is the most interesting question you can ask to get to know someone?
09.06.2025 10:43
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you like the “69” position? Do you prefer to be on top or bottom?
Teacher/Student Stranger/One Night Stand
1- What was your first impression of me? Has it changed?
Nurse/Patient Celebrity/Fan
9- What’s your favorite season and why? What’s your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What do you dislike about me? I asked you to be 100% honest.
Prisoner/Prison Guard Landlord/Tenant
Has your wife made you a cuckold?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
*** Deal Breaker Questions ***
Are there any nude pictures of women with big tits?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
If yes, what?
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32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
Is The Last of Us Part 2 really as woke as people say it is?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
12- What is the weirdest thing you've ever eaten?
82~ Do you have any fantasies involving Role-Playing?
27- What was/ is nickname? Does it have a meaning behind it?
21~ What was the best date you ever went on? What has been the worst?
71~ Would you give your partner a hand or foot job? Would you receive one?
Family Relation Age Play
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Any that are a turn off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
34- Ever been to a concert? What was your favorite? Who would you like to see?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
19~ Who/when was your first “heartbreak”?
28- What are some things that people do that irritate you?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
Why are white women not interested in dating Asian men? Are they not attractive to you at all?
What is your view on sex? Meaning, When/Where/ How often/
Can you Deep Throat? Do you like the taste of yourself?
The Ice Breaker Questions
8- What are your thoughts on politics?
How well do you know me? And some of your thoughts about me
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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37- Do you like your name? If you could change it, what would you change it too?
48~ Do you have any siblings? Are you close to your family?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
89~ Do you like taking showers together?
36~ What is your favorite time of day to have sex/make love?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
42~ What’s your biggest regret in life?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
11~ Have you ever been caught by your parents or children or others while having sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
(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…)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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)
Repairman/Lonely Wife Virgin/Experienced
If NO, would you ever have one? Would it be with 2 men or 2 women?
61~ How willing would you be to try new sexual positions?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
31- If given a chance to be immortal, would you take it? Why?
Do you like it when they show and tell you what they want?
I would allow you to do it… What would you do to me?
What would you say to prove to yourself that it was really you?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
10- List 5 of your top pet peeves.
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
92~ Everyone needs a “safe” word. What is yours?
13- What is the craziest/scariest thing you've ever done?
How about if they talk dirty and/or call you names?
7- What are your thoughts on religion? Is there an afterlife?
60~ How important is oral sex? Do you like receiving? Do you like giving?
81~ Do you have any kinks and/or fetishes?
10- What is your favorite family tradition? What’s your least favorite?
39~ What are your love languages?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
51~ Are you willing to play adult games with your partner?
7-What do I do in bed that drives you wild? How about, what turns you off?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
9~ How many times over your lifetime do you think you have had sex so far?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
1~ How old were you when you had your first kiss? Who? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
32- What's your greatest talent? Can I see it right now?
28~ What are some things that turn on? What is your biggest turn on?
Master/Slave Boss/Maid
34~ Do you like the lights on or off during sex?
3- What Superhero or Superpower would you want to be/have?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
19- Do/have you smoked? What do you prefer? How often?
11- List at least 5 things on your bucket list. Have you done any of them already?
38~ Share your most embarrassing sexual memory?
65~ Describe the best orgasm you’ve ever had? Care to share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Would you ever want to be woken up with oral and/or intercourse?
Have you ever? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Nothing too Serious
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
10~ How many dates are necessary before you to have sex with someone?
33- If you could visit any time period, when would you pick? Please explain why?
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…
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
23- What is your dream job? What was it as a child?
29- How superstitious are you?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Will you cheat again? How can, you be sure? Define what cheating is to you.
13- What’s your favorite drink? What’s your least favorite?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
4- For a pet, Cat, dog or other?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
17- Have you ever done drugs? Which ones? How often?
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…
13~ Is there a difference between, making love, having sex, and fucking?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Would you do it again, and would you rather 2 females or 2 males?
92~ Have you ever had or have an STD? How many? What was it?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
84~ How do you feel about reading/listening to adult stories?
9- Is there something you’ve always wanted to ask me but you’re afraid?
How many partners have you had oral sex with? Who? Care to Share?
Over time has your thoughts on sex changed?
13- How about having a certain hair cut/style?
18~ Who/when was your first “crush”?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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?
19- What’s your favorite fairytale? What’s your least favorite?
How old are you? Male or Female?
14- What's your favorite dessert? Do you a least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
83~ How do you feel about Porn?
21- What's your favorite way to spend a weekend or time off?
That one or two things that made you go hmmmm, OMG or wow!
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
If you win, what will you make them do?
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?
62~ Have you used adult toys?
*** Questions about Relationships/Past ***
41~ Are there moments in your past that you would want to change? Please share 3 of them.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
5- Have you ever been hypnotized? Would you allow yourself to be?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Please share Did you stop?
52~ Are you willing to make “those types” of bets with your partner?
49~ How many times have you been married? Why did they end?
What is your favorite position? Why?
8- What's your favorite flavor of ice cream? Do you a least favorite?
*** What’s Your Favorite…? ***
18- How often do you drink alcohol? What is your favorite drink?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
50~ How many children do you have? What are their ages?
Do you watch it? What is your favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you have a favorite? Is it ok if your partner does?
53~ How much can you tell me about the one thing you are most passionate about?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
9- If you could have three wishes, what would they be? Why?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
76~ Have you had a threesome? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
15- What's your favorite saying? What word or phrase is your least favorite?
Would you read them together?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
3- What’s your favorite smell? Do you a least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
5~ When you first started having sex, was it what you thought it would be?
If YES, was it with 2 men or 2 women? Did you enjoy it?
52~ What are your hobbies?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
12- What’s your favorite food? What’s your least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
1- What’s your favorite animal? Do you a least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
If you say it, I will stop, and we can talk about it when you are ready.
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?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Model/Photographer Police/Criminal
7- What if a person smells a certain way? 8- How about smoking?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
30~ What's something unexpected that turns you on?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
45~ How do you feel about me blindfolding you? How about blindfolding me?
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?
* Give a rating for each one (0-100)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
6- Do you have dreams? Can you remember them? What do you usually dream about?
11- What's your favorite restaurant? What’s your least favorite?
Would you mind if your partner watched it? How about together vs alone?
2- What’s your favorite color? Do you a least favorite?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
*** Random Questions ***
33- Beach or Mountains? Or is there another place to like better?
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,
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
58~ Have you ever taken Nude or Hard-core photos and/or videos? 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?
22- What is your favorite childhood memory? What is your least favorite?
Would /have you ever given your partner a lap dance and Striptease?
44~ Care to share something about yourself that no one else knows about you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
*** Questions About Me ***
What have you learned about yourself that you did not before this?
Any that are a turn off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Doctor/Nurse Stripper/Client
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
You know that I will be 100% truthful, so ask.
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)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
15~ Have you ever been “in love”? Who? Care to Share?
48~ Have you ever paid or been paid for sex?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
20- What’s your favorite candy? What’s your least favorite?
51~ What tends to bring a smile to your face?
15- What bad habit do you wish you could quit? Do you have any addictions?
Get this wrong and this could mean the end… :-) some funny, some not…
11- How about if they like a certain sports team? 12-How about drinking too much?
Does the thought excite you? Care to share?
Escort/Client Job Applicant/Hiring Manager
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
How many times do you think you have “made love”?
Do you think this brought you closer together?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Would you allow me to clean every part of your body with my soapy hands and fingers?
67~ Do you like it when your partner moans and/or is vocal during sex?
What was the longest? What was the shortest?
26~ What side of the bed do you sleep on?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
47~ What would be your dream job and why?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
What have you learned about me that was new and/or surprising?
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?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®