What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 00:12
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Why am I sweating so much at night even though my room is really cold?
18- How often do you drink alcohol? What is your favorite drink?
19- Do/have you smoked? What do you prefer? How often?
11- How about if they like a certain sports team? 12-How about drinking too much?
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44~ Care to share something about yourself that no one else knows about you?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
15~ Have you ever been “in love”? Who? Care to Share?
If there was only one man remaining on the Earth, would this be regarded as extinction?
5~ When you first started having sex, was it what you thought it would be?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Are there any queer Space Marine Legion in Warhammer 30k or 40k?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
1~ How old were you when you had your first kiss? Who? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
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How many times do you think you have “made love”?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Why are black people harassed more by police officers?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
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?
Would /have you ever given your partner a lap dance and Striptease?
What would you say to prove to yourself that it was really you?
45~ How do you feel about me blindfolding you? How about blindfolding me?
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5- Have you ever been hypnotized? Would you allow yourself to be?
92~ Have you ever had or have an STD? How many? What was it?
How many partners have you had oral sex with? Who? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Would you ever want to be woken up with oral and/or intercourse?
7-What do I do in bed that drives you wild? How about, what turns you off?
How do you know if your husband loves you truly and deeply?
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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52~ Are you willing to make “those types” of bets with your partner?
Repairman/Lonely Wife Virgin/Experienced
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?
Is it ok to be spanked by your parents if you are not in bed in your set bedtime?
10- List 5 of your top pet peeves.
17- What’s your favorite holiday? What’s your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
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Do you like the “69” position? Do you prefer to be on top or bottom?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What's an uncomfortable truth you've learned to accept?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Would you read them together?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
89~ Do you like taking showers together?
Would you allow me to clean every part of your body with my soapy hands and fingers?
3- What’s your favorite smell? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Any that are a turn off?
*** Questions About Me ***
61~ How willing would you be to try new sexual positions?
51~ What tends to bring a smile to your face?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
48~ Do you have any siblings? Are you close to your family?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What is your view on sex? Meaning, When/Where/ How often/
1- What’s your favorite animal? Do you a least favorite?
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?
10- What is your favorite family tradition? What’s your least favorite?
What was the longest? What was the shortest?
11- What's your favorite restaurant? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Nurse/Patient Celebrity/Fan
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
25~ How do you feel about PDA? (Public Display of Affection)
51~ Are you willing to play adult games with your partner?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
19~ Who/when was your first “heartbreak”?
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…
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
28- What are some things that people do that irritate you?
9- If you could have three wishes, what would they be? Why?
Nothing too Serious
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
*** Questions about Relationships/Past ***
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Would you mind if your partner watched it? How about together vs alone?
Will you cheat again? How can, you be sure? Define what cheating is to you.
40~ What’s the weirdest place you’ve ever had sex?
32- What's your greatest talent? Can I see it right now?
*** What’s Your Favorite…? ***
Family Relation Age Play
Model/Photographer Police/Criminal
33- If you could visit any time period, when would you pick? Please explain why?
What have you learned about me that was new and/or surprising?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
20- What’s your favorite candy? What’s your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Doctor/Nurse Stripper/Client
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) 😊
If yes, what?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
*** Random Questions ***
How old are you? Male or Female?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
92~ Everyone needs a “safe” word. What is yours?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Teacher/Student Stranger/One Night Stand
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
38~ Share your most embarrassing sexual memory?
12- What is the weirdest thing you've ever eaten?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
17- Have you ever done drugs? Which ones? How often?
13~ Is there a difference between, making love, having sex, and fucking?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Do you think this brought you closer together?
15- What bad habit do you wish you could quit? Do you have any addictions?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
23- What is your dream job? What was it as a child?
How well do you know me? And some of your thoughts about me
(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…)
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
9- Is there something you’ve always wanted to ask me but you’re afraid?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
31- If given a chance to be immortal, would you take it? Why?
70~ Would/do you have/like anal sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
If YES, was it with 2 men or 2 women? Did you enjoy it?
81~ Do you have any kinks and/or fetishes?
10~ How many dates are necessary before you to have sex with someone?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you have a favorite? Is it ok if your partner does?
48~ Have you ever paid or been paid for sex?
Escort/Client Job Applicant/Hiring Manager
60~ How important is oral sex? Do you like receiving? Do you like giving?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
26~ What side of the bed do you sleep on?
You know that I will be 100% truthful, so ask.
47~ What would be your dream job and why?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
36~ What is your favorite time of day to have sex/make love?
12- What’s your favorite food? What’s your least favorite?
33- Beach or Mountains? Or is there another place to like better?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
29~ What are some things that turn you off? What is your biggest turn off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If you win, what will you make them do?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
8- What are your thoughts on politics?
That one or two things that made you go hmmmm, OMG or wow!
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Is it ok for a man to perform oral sex after he has ejaculated inside of 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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
28~ What are some things that turn on? What is your biggest turn on?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
* Give a rating for each one (0-100)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Can you Deep Throat? Do you like the taste of yourself?
What do you dislike about me? I asked you to be 100% honest.
9~ How many times over your lifetime do you think you have had sex so far?
1- What was your first impression of me? Has it changed?
Prisoner/Prison Guard Landlord/Tenant
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Does the thought excite you? Care to share?
How about if they talk dirty and/or call you names?
11- List at least 5 things on your bucket list. Have you done any of them already?
11~ Have you ever been caught by your parents or children or others while having sex?
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?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Do you like it when they show and tell you what they want?
3- What Superhero or Superpower would you want to be/have?
13- How about having a certain hair cut/style?
7- What are your thoughts on religion? Is there an afterlife?
Over time has your thoughts on sex changed?
53~ How much can you tell me about the one thing you are most passionate about?
34~ Do you like the lights on or off during sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Master/Slave Boss/Maid
9- What’s your favorite season and why? What’s your least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
2- What’s your favorite color? Do you a least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
82~ Do you have any fantasies involving Role-Playing?
42~ What’s your biggest regret in life?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
3- Should Pluto still be considered a planet? 4- How about smoking?
4- For a pet, Cat, dog or other?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
76~ Have you had a threesome? 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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
19- What’s your favorite fairytale? What’s your least favorite?
52~ What are your hobbies?
14- What is an embarrassing moment in your life? How about your most embarrassing?
37- Do you like your name? If you could change it, what would you change it too?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
What have you learned about yourself that you did not before this?
I would allow you to do it… What would you do to me?
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…
Have you ever? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Please share Did you stop?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
30~ What's something unexpected that turns you on?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Get this wrong and this could mean the end… :-) some funny, some not…
65~ Describe the best orgasm you’ve ever had? Care to share?
If you say it, I will stop, and we can talk about it when you are ready.
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
6- Do you have dreams? Can you remember them? What do you usually dream about?
13- What is the craziest/scariest thing you've ever done?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
29- How superstitious are you?
The Ice Breaker Questions
18~ Who/when was your first “crush”?
39~ What are your love languages?
14- What's your favorite dessert? Do you a least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
49~ How many times have you been married? Why did they end?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
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
18- What’s your favorite way to relax after a long day? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
*** Deal Breaker Questions ***
62~ Have you used adult toys?
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
15- What's your favorite saying? What word or phrase is your least favorite?
83~ How do you feel about Porn?
21~ What was the best date you ever went on? What has been the worst?
Any that are a turn off?
50~ How many children do you have? What are their ages?
84~ How do you feel about reading/listening to adult stories?
22- Do you have any birth marks? How about scars? Care to share how you got them?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you watch it? What is your favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What is your favorite position? Why?
21- What's your favorite way to spend a weekend or time off?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?