What is the most interesting question you can ask to get to know someone?
Last Updated: 22.06.2025 00:41
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
80~ Share your top three fantasies/desires. (Be detailed) đ
Get this wrong and this could mean the end⌠:-) some funny, some notâŚ
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20- Whatâs your favorite candy? Whatâs your least favorite?
How old are you? Male or Female?
83~ How do you feel about Porn?
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78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
The Ice Breaker Questions
33- Beach or Mountains? Or is there another place to like better?
Do you think this brought you closer together?
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?
Aut explicabo sapiente quis consequuntur fuga consectetur fugit.
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
32- What's your greatest talent? Can I see it right now?
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Why am I so jealous towards couples? Why am I tired of being single and feel my life is over?
Take the short quiz here @ Discover Your Love LanguageÂŽ - The 5 Love LanguagesÂŽ
24~ What are your expectations in a relationship? (I know a very big question, take your time)
50~ How many children do you have? What are their ages?
89~ Do you like taking showers together?
42~ Whatâs your biggest regret in life?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŚ
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14- What's your favorite dessert? Do you a least favorite?
Over time has your thoughts on sex changed?
52~ Are you willing to make âthose typesâ of bets with your partner?
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Model/Photographer Police/Criminal
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Have you ever? Care to Share?
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
10- What is your favorite family tradition? Whatâs your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
16~ Do you believe in âsoulmatesâ? Have you found yours? 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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What is your view on sex? Meaning, When/Where/ How often/
How about if they talk dirty and/or call you names?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Is Veuve Clicquot Brut a good champagne?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
31- If given a chance to be immortal, would you take it? Why?
14- What is an embarrassing moment in your life? How about your most embarrassing?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
If yes, what?
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
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?
10~ How many dates are necessary before you to have sex with someone?
9- If you could have three wishes, what would they be? Why?
23- What is your dream job? What was it as a child?
21- What's your favorite way to spend a weekend or time off?
14 â Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Would you allow me to clean every part of your body with my soapy hands and fingers?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What would you say to prove to yourself that it was really you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
9- Is there something youâve always wanted to ask me but youâre afraid?
What have you learned about me that was new and/or surprising?
8- What are your thoughts on politics?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Would you ever want to be woken up with oral and/or intercourse?
71~ Would you give your partner a hand or foot job? Would you receive one?
Do you have a favorite? Is it ok if your partner does?
Nurse/Patient Celebrity/Fan
48~ Do you have any siblings? Are you close to your family?
30~ What's something unexpected that turns you on?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
13- How about having a certain hair cut/style?
84~ How do you feel about reading/listening to adult stories?
36- Do you play video games? What is your favorite? Do you a least favorite?
29- How superstitious are you?
If you say it, I will stop, and we can talk about it when you are ready.
Does the thought excite you? Care to share?
Doctor/Nurse Stripper/Client
*** Questions about Relationships/Past ***
Do you like the â69â position? Do you prefer to be on top or bottom?
70~ Would/do you have/like anal sex?
3- What Superhero or Superpower would you want to be/have?
51~ What tends to bring a smile to your face?
Prisoner/Prison Guard Landlord/Tenant
12- Whatâs your favorite food? Whatâs your least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
That one or two things that made you go hmmmm, OMG or wow!
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
18~ Who/when was your first âcrushâ?
13~ Is there a difference between, making love, having sex, and fucking?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
26~ What side of the bed do you sleep on?
What is your favorite position? Why?
7- What are your thoughts on religion? Is there an afterlife?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
36~ What is your favorite time of day to have sex/make love?
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
28- What are some things that people do that irritate you?
7-What do I do in bed that drives you wild? How about, what turns you off?
60~ How important is oral sex? Do you like receiving? Do you like giving?
12- What is the weirdest thing you've ever eaten?
*** Whatâs Your FavoriteâŚ? ***
92~ Have you ever had or have an STD? How many? What was it?
Teacher/Student Stranger/One Night Stand
49~ How many times have you been married? Why did they end?
*** Deal Breaker Questions ***
6- Do you have dreams? Can you remember them? What do you usually dream about?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Would you mind if your partner watched it? How about together vs alone?
22- Do you have any birth marks? How about scars? Care to share how you got them?
15- What's your favorite saying? What word or phrase is your least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
*** Questions About Me ***
15~ Have you ever been âin loveâ? Who? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
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?
How many times do you think you have âmade loveâ?
22- What is your favorite childhood memory? What is your least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
I would allow you to do it⌠What would you do to me?
37- Do you like your name? If you could change it, what would you change it too?
Do you like it when they show and tell you what they want?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
92~ Everyone needs a âsafeâ word. What is yours?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
19~ Who/when was your first âheartbreakâ?
34~ Do you like the lights on or off during sex?
What have you learned about yourself that you did not before this?
25~ How do you feel about PDA? (Public Display of Affection)
48~ Have you ever paid or been paid for sex?
* Give a rating for each one (0-100)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
1- What was your first impression of me? Has it changed?
11- How about if they like a certain sports team? 12-How about drinking too much?
3- Whatâs your favorite smell? Do you a least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
85~ If you gave me a âfree Passâ to have me do anything for one hour, what would you want me to do to you?
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
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 âPASSâ 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 yourselfâŚ
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
If you win, what will you make them do?
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couplesâ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETCâŚ)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Will you cheat again? How can, you be sure? Define what cheating is to you.
11- List at least 5 things on your bucket list. Have you done any of them already?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
1~ How old were you when you had your first kiss? Who? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Any that are a turn off?
3- What was the most surprising thing youâve learned about me throughout our relationship?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŚ
3- Should Pluto still be considered a planet? 4- How about smoking?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
28~ What are some things that turn on? What is your biggest turn on?
51~ Are you willing to play adult games with your partner?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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?
Repairman/Lonely Wife Virgin/Experienced
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Escort/Client Job Applicant/Hiring Manager
38~ Share your most embarrassing sexual memory?
13- What is the craziest/scariest thing you've ever done?
45~ How do you feel about me blindfolding you? How about blindfolding me?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
4- For a pet, Cat, dog or other?
17- Have you ever done drugs? Which ones? How often?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
76~ Have you had a threesome? Care to Share?
52~ What are your hobbies?
Piecing, tattoo, color hair, dress up a certain way, it could be anything⌠Shave meâŚ
81~ Do you have any kinks and/or fetishes?
18- How often do you drink alcohol? What is your favorite drink?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
65~ Describe the best orgasm youâve ever had? Care to share?
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
2- Whatâs your favorite color? Do you a least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
11- What's your favorite restaurant? Whatâs your least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
33- If you could visit any time period, when would you pick? Please explain why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
7- What if a person smells a certain way? 8- How about smoking?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
47~ What would be your dream job and why?
Please share Did you stop?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
15- What bad habit do you wish you could quit? Do you have any addictions?
How well do you know me? And some of your thoughts about me
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
19- Whatâs your favorite fairytale? Whatâs your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Do you watch it? What is your favorite?
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 togetherâŚ
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
44~ Care to share something about yourself that no one else knows about you?
14- Do you have a âDeal Breakerâ, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
17- Whatâs your favorite holiday? Whatâs your least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Family Relation Age Play
62~ Have you used adult toys?
39~ What are your love languages?
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?
Master/Slave Boss/Maid
You know that I will be 100% truthful, so ask.
What was the longest? What was the shortest?
Can you Deep Throat? Do you like the taste of yourself?
What do you dislike about me? I asked you to be 100% honest.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
5~ When you first started having sex, was it what you thought it would be?
Nothing too Serious
Would you read them together?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
10- List 5 of your top pet peeves.
19- Do/have you smoked? What do you prefer? How often?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
27- What was/ is nickname? Does it have a meaning behind it?
40~ Whatâs the weirdest place youâve ever had sex?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
9- Whatâs your favorite season and why? Whatâs your least favorite?
61~ How willing would you be to try new sexual positions?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
*** Random Questions ***
11~ Have you ever been caught by your parents or children or others while having sex?
13- Whatâs your favorite drink? Whatâs your least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
1- Whatâs your favorite animal? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Would you do it again, and would you rather 2 females or 2 males?
How many partners have you had oral sex with? Who? Care to Share?
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?
85~ If I gave you a âFree Passâ for you to do anything to me for one hour, knowing that no matter what you did,
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
29~ What are some things that turn you off? What is your biggest turn off?