What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 06:10
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
What does it mean when we dream about demons, ghosts, monsters, etc.?
50~ How many children do you have? What are their ages?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
What’s one positive trait you’ve gained because of BPD?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Is it ok to be spanked by your parents if you are not in bed in your set bedtime?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
What is your favorite position? Why?
What is the meaning of xx in texting?
What do you dislike about me? I asked you to be 100% honest.
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
What type of sex do women prefer, oral, anal, or vaginal?
1- What’s your favorite animal? Do you a least favorite?
26~ What side of the bed do you sleep on?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What are the strangest parts of The Bible?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Model/Photographer Police/Criminal
6- Do you have dreams? Can you remember them? What do you usually dream about?
Prisoner/Prison Guard Landlord/Tenant
8- What's your favorite flavor of ice cream? Do you a least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Major supermarket chain workers start strike across 4 cities - TheStreet
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
32- What's your greatest talent? Can I see it right now?
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?
Why does it itch on my vulva, uterus, and sides of my vagina, but it doesn't itch inside the vagina?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
23- What is your dream job? What was it as a child?
Was Daenerys' downfall inevitable after she left Meereen in Game of Thrones?
33- Beach or Mountains? Or is there another place to like better?
70~ Would/do you have/like anal 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?
How can I earn money through OnlyFans?
1~ How old were you when you had your first kiss? Who? Care to Share?
17- Have you ever done drugs? Which ones? How often?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Why do men suck dick? Me, I can't get enough
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
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4- For a pet, Cat, dog or other?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
*** Deal Breaker Questions ***
Escort/Client Job Applicant/Hiring Manager
Get this wrong and this could mean the end… :-) some funny, some not…
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
1- What was your first impression of me? Has it changed?
14- What's your favorite dessert? Do you a least favorite?
28- What are some things that people do that irritate you?
I would allow you to do it… What would you do to me?
*** Questions about Relationships/Past ***
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
19~ Who/when was your first “heartbreak”?
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?
37- Do you like your name? If you could change it, what would you change it too?
21- What's your favorite way to spend a weekend or time off?
Master/Slave Boss/Maid
15- What bad habit do you wish you could quit? Do you have any addictions?
5- Have you ever been hypnotized? Would you allow yourself to be?
What is your favorite toy? Ever wanted to try a specific toy?
3- What Superhero or Superpower would you want to be/have?
Do you think this brought you closer together?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
27- What was/ is nickname? Does it have a meaning behind it?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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…
3- What’s your favorite smell? Do you a least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
92~ Everyone needs a “safe” word. What is yours?
81~ Do you have any kinks and/or fetishes?
19- Do/have you smoked? What do you prefer? How often?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
How many times do you think you have “made love”?
40~ What’s the weirdest place you’ve ever had sex?
Over time has your thoughts on sex changed?
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)
Will you kiss after your partner has gone down on you? Swallow or spit semen?
You know that I will be 100% truthful, so ask.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
12- What is the weirdest thing you've ever eaten?
Do you have a favorite? Is it ok if your partner does?
67~ Do you like it when your partner moans and/or is vocal during sex?
34~ Do you like the lights on or off during sex?
10- List 5 of your top pet peeves.
Do you watch it? What is your 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?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
If you say it, I will stop, and we can talk about it when you are ready.
Would /have you ever given your partner a lap dance and Striptease?
What is your view on sex? Meaning, When/Where/ How often/
29~ What are some things that turn you off? What is your biggest turn off?
52~ What are your hobbies?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Any that are a turn off?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
19- What’s your favorite fairytale? What’s your least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
15~ Have you ever been “in love”? Who? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
38~ Share your most embarrassing sexual memory?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
51~ What tends to bring a smile to your face?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Would you mind if your partner watched it? How about together vs alone?
83~ How do you feel about Porn?
76~ Have you had a threesome? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
7- What if a person smells a certain way? 8- How about smoking?
Teacher/Student Stranger/One Night Stand
3- Should Pluto still be considered a planet? 4- How about smoking?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
5~ When you first started having sex, was it what you thought it would be?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
9- Is there something you’ve always wanted to ask me but you’re afraid?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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?
9~ How many times over your lifetime do you think you have had sex so far?
48~ Have you ever paid or been paid for sex?
If NO, would you ever have one? Would it be with 2 men or 2 women?
18~ Who/when was your first “crush”?
92~ Have you ever had or have an STD? How many? What was it?
36~ What is your favorite time of day to have sex/make love?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
22- Do you have any birth marks? How about scars? Care to share how you got them?
Family Relation Age Play
89~ Do you like taking showers together?
13~ Is there a difference between, making love, having sex, and fucking?
Nurse/Patient Celebrity/Fan
Would you ever want to be woken up with oral and/or intercourse?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
31- If given a chance to be immortal, would you take it? Why?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
42~ What’s your biggest regret in life?
2- What’s your favorite color? Do you a least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
61~ How willing would you be to try new sexual positions?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Do you like the “69” position? Do you prefer to be on top or bottom?
Doctor/Nurse Stripper/Client
11- What's your favorite restaurant? What’s your least favorite?
What have you learned about me that was new and/or surprising?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
39~ What are your love languages?
Would you do it again, and would you rather 2 females or 2 males?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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…
*** Random Questions ***
Do you like it when they show and tell you what they want?
36- Do you play video games? What is your favorite? Do you a least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
17- What’s your favorite holiday? What’s your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
44~ Care to share something about yourself that no one else knows about you?
Will you cheat again? How can, you be sure? Define what cheating is to you.
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
8- What are your thoughts on politics?
How about if they talk dirty and/or call you names?
21~ What was the best date you ever went on? What has been the worst?
10- What is your favorite family tradition? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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,
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Nothing too Serious
That one or two things that made you go hmmmm, OMG or wow!
Can you Deep Throat? Do you like the taste of yourself?
Does the thought excite you? Care to share?
Would you read them together?
Have you ever? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
9- What’s your favorite season and why? What’s your least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
13- What is the craziest/scariest thing you've ever done?
How old are you? Male or Female?
13- How about having a certain hair cut/style?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
33- If you could visit any time period, when would you pick? Please explain why?
How well do you know me? And some of your thoughts about me
Any that are a turn off?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
9- If you could have three wishes, what would they be? Why?
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?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
49~ How many times have you been married? Why did they end?
28~ What are some things that turn on? What is your biggest turn on?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
The Ice Breaker Questions
49~ If you could, would you want to be the opposite sex for a day, week, or year?
22- What is your favorite childhood memory? What is your least favorite?
If you win, what will you make them do?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
7- What are your thoughts on religion? Is there an afterlife?
What have you learned about yourself that you did not before this?
51~ Are you willing to play adult games with your partner?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
20- What’s your favorite candy? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
What would you say to prove to yourself that it was really you?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
*** Questions About Me ***
48~ Do you have any siblings? Are you close to your family?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
29- How superstitious are you?
18- How often do you drink alcohol? What is your favorite drink?
If yes, what?
60~ How important is oral sex? Do you like receiving? Do you like giving?
What was the longest? What was the shortest?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
11- How about if they like a certain sports team? 12-How about drinking too much?
52~ Are you willing to make “those types” of bets with your partner?
11~ Have you ever been caught by your parents or children or others while having sex?
11- List at least 5 things on your bucket list. Have you done any of them already?
30~ What's something unexpected that turns you on?
* Give a rating for each one (0-100)
(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…)
Please share Did you stop?
Would you allow me to clean every part of your body with my soapy hands and fingers?
13- What’s your favorite drink? What’s your least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
12- What’s your favorite food? What’s your least favorite?
82~ Do you have any fantasies involving Role-Playing?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
53~ How much can you tell me about the one thing you are most passionate about?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
7-What do I do in bed that drives you wild? How about, what turns you off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
62~ Have you used adult toys?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
47~ What would be your dream job and why?
*** What’s Your Favorite…? ***
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
10~ How many dates are necessary before you to have sex with someone?
How many partners have you had oral sex with? Who? Care to Share?