What is the most interesting question you can ask to get to know someone?
Last Updated: 16.06.2025 23:59
26~ What side of the bed do you sleep on?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
*** Deal Breaker Questions ***
How did Kate Mulgrew feel about Jeri Ryan joining the cast of Star Trek: Voyager?
If you win, what will you make them do?
7- What are your thoughts on religion? Is there an afterlife?
11- How about if they like a certain sports team? 12-How about drinking too much?
If my lovely sister sleeps with my boyfriend, what should I do about her?
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What is the best case of “You just picked a fight with the wrong person” that you've witnessed?
19- What’s your favorite fairytale? What’s your least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Can you explain the difference between an ego, soul, mind, and consciousness?
Family Relation Age Play
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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…
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Do you have a favorite? Is it ok if your partner does?
10~ How many dates are necessary before you to have sex with someone?
53~ How much can you tell me about the one thing you are most passionate about?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
32- What's your greatest talent? Can I see it right now?
Why do I want to be caught sucking dick by my wife?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
Escort/Client Job Applicant/Hiring Manager
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would /have you ever given your partner a lap dance and Striptease?
Have you ever? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What type of fish is best for fish tacos?
10- What is your favorite family tradition? What’s your least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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Would you mind if your partner watched it? How about together vs alone?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
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's your favorite dessert? Do you a least favorite?
Would you ever want to be woken up with oral and/or intercourse?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Is there a possibility that we are living in a simulation and that there is a concept of rebirth?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
*** Questions about Relationships/Past ***
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Any that are a turn off?
89~ Do you like taking showers together?
76~ Have you had a threesome? Care to Share?
61~ How willing would you be to try new sexual positions?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Doctor/Nurse Stripper/Client
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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?
9- If you could have three wishes, what would they be? Why?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Nothing too Serious
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
15- What bad habit do you wish you could quit? Do you have any addictions?
3- What Superhero or Superpower would you want to be/have?
82~ Do you have any fantasies involving Role-Playing?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
22- What is your favorite childhood memory? What is your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
36~ What is your favorite time of day to have sex/make love?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
15~ Have you ever been “in love”? Who? Care to Share?
51~ Are you willing to play adult games with your partner?
* Give a rating for each one (0-100)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
What have you learned about yourself that you did not before this?
Does the thought excite you? Care to share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
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?
*** What’s Your Favorite…? ***
The Ice Breaker Questions
What is your favorite toy? Ever wanted to try a specific toy?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
5~ When you first started having sex, was it what you thought it would be?
30- Do you prefer living in the countryside, in a town, or in a big city? 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?
19~ Who/when was your first “heartbreak”?
Do you think this brought you closer together?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Will you cheat again? How can, you be sure? Define what cheating is to you.
4- For a pet, Cat, dog or other?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
7-What do I do in bed that drives you wild? How about, what turns you off?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
48~ Have you ever paid or been paid for sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
3- Should Pluto still be considered a planet? 4- How about smoking?
12- What is the weirdest thing you've ever eaten?
9~ How many times over your lifetime do you think you have had sex so far?
20- What’s your favorite candy? What’s your least favorite?
Master/Slave Boss/Maid
65~ Describe the best orgasm you’ve ever had? Care to share?
1- What’s your favorite animal? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Any that are a turn off?
31- If given a chance to be immortal, would you take it? Why?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
How old are you? Male or Female?
7- What if a person smells a certain way? 8- How about smoking?
30~ What's something unexpected that turns you on?
17- What’s your favorite holiday? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
27- What was/ is nickname? Does it have a meaning behind it?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Can you Deep Throat? Do you like the taste of yourself?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
18~ Who/when was your first “crush”?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
21~ What was the best date you ever went on? What has been the worst?
83~ How do you feel about Porn?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
29- How superstitious are you?
28~ What are some things that turn on? What is your biggest turn on?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
25~ How do you feel about PDA? (Public Display of Affection)
39~ What are your love languages?
How well do you know me? And some of your thoughts about me
81~ Do you have any kinks and/or fetishes?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
34- Ever been to a concert? What was your favorite? Who would you like to see?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
How many times do you think you have “made love”?
2- What’s your favorite color? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
5- Have you ever been hypnotized? Would you allow yourself to be?
Would you do it again, and would you rather 2 females or 2 males?
Over time has your thoughts on sex changed?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
6- What’s your favorite TV series? Do you have a favorite genre? 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…
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…
*** Random Questions ***
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
11- What's your favorite restaurant? What’s your least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
Would you read them together?
33- Beach or Mountains? Or is there another place to like better?
45~ How do you feel about me blindfolding you? How about blindfolding me?
40~ What’s the weirdest place you’ve ever had sex?
13- What is the craziest/scariest thing you've ever done?
What would you say to prove to yourself that it was really you?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
36- Do you play video games? What is your favorite? Do you a least favorite?
17- Have you ever done drugs? Which ones? How often?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Do you watch it? What is your favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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?
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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
*** Questions About Me ***
Nurse/Patient Celebrity/Fan
1~ How old were you when you had your first kiss? Who? Care to Share?
28- What are some things that people do that irritate you?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Please share Did you stop?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
8- What are your thoughts on politics?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
23- What is your dream job? What was it as a child?
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)
I would allow you to do it… What would you do to me?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
67~ Do you like it when your partner moans and/or is vocal during sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
21- What's your favorite way to spend a weekend or time off?
Would you allow me to clean every part of your body with my soapy hands and fingers?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
38~ Share your most embarrassing sexual memory?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Teacher/Student Stranger/One Night Stand
1- What was your first impression of me? Has it changed?
29~ What are some things that turn you off? What is your biggest turn off?
Do you like the “69” position? Do you prefer to be on top or bottom?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
37- Do you like your name? If you could change it, what would you change it too?
If yes, what?
That one or two things that made you go hmmmm, OMG or wow!
What was the longest? What was the shortest?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
11- List at least 5 things on your bucket list. Have you done any of them already?
13- What’s your favorite drink? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
11~ Have you ever been caught by your parents or children or others while having sex?
Prisoner/Prison Guard Landlord/Tenant
34~ Do you like the lights on or off during sex?
What is your favorite position? Why?
52~ Are you willing to make “those types” of bets with your partner?
How about if they talk dirty and/or call you names?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How many partners have you had oral sex with? Who? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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.
Model/Photographer Police/Criminal
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
You know that I will be 100% truthful, so ask.
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
70~ Would/do you have/like anal sex?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Repairman/Lonely Wife Virgin/Experienced
8- What's your favorite flavor of ice cream? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
92~ Have you ever had or have an STD? How many? What was it?
49~ How many times have you been married? Why did they end?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Get this wrong and this could mean the end… :-) some funny, some not…
62~ Have you used adult toys?
48~ Do you have any siblings? Are you close to your family?
14- What is an embarrassing moment in your life? How about your most embarrassing?
47~ What would be your dream job and why?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
42~ What’s your biggest regret in life?
Do you like it when they show and tell you what they want?
44~ Care to share something about yourself that no one else knows about you?
13- How about having a certain hair cut/style?
18- How often do you drink alcohol? What is your favorite drink?
What do you dislike about me? I asked you to be 100% honest.
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What is your view on sex? Meaning, When/Where/ How often/
52~ What are your hobbies?
9- What’s your favorite season and why? What’s your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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,
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?
84~ How do you feel about reading/listening to adult stories?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
What have you learned about me that was new and/or surprising?
51~ What tends to bring a smile to your face?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
80~ Share your top three fantasies/desires. (Be detailed) 😊
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
15- What's your favorite saying? What word or phrase is your least favorite?
19- Do/have you smoked? What do you prefer? How often?
12- What’s your favorite food? What’s your least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
(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…)