What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 00:56
5- Have you ever been hypnotized? Would you allow yourself to be?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
62~ Have you used adult toys?
Do empaths fall easier for abusive people?
Prisoner/Prison Guard Landlord/Tenant
13- How about having a certain hair cut/style?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Scientists discover that dogs can alert humans to this quickly-spreading disease - Earth.com
52~ Are you willing to make “those types” of bets with your partner?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Please share Did you stop?
10- What is your favorite family tradition? What’s your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Unreleased GeForce RTX 3080 Ti with 20GB memory spotted on eBay - VideoCardz.com
18- What’s your favorite way to relax after a long day? What’s your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
21- What's your favorite way to spend a weekend or time off?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Has any man licked his wife's vagina while another man had sex with her?
10~ How many dates are necessary before you to have sex with someone?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
13- What’s your favorite drink? What’s your least favorite?
What are some signs he is deeply in love with you?
* Give a rating for each one (0-100)
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?
You know that I will be 100% truthful, so ask.
Was Adam white or black (African)?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
40~ What’s the weirdest place you’ve ever had sex?
27- What was/ is nickname? Does it have a meaning behind it?
How do the youth in Taiwan perceive their national identity in relation to China?
What would you say to prove to yourself that it was really you?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Can a cop pull you over walking home asking why you are out so late?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
Family Relation Age Play
Is it true that most women like alpha males?
70~ Would/do you have/like anal sex?
23- What is your dream job? What was it as a child?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What are some tips for balancing chores, work, and family life as an adult with children?
3- Should Pluto still be considered a planet? 4- How about smoking?
3- What Superhero or Superpower would you want to be/have?
11- How about if they like a certain sports team? 12-How about drinking too much?
*** Deal Breaker Questions ***
Do you think this brought you closer together?
9- What’s your favorite season and why? What’s your least favorite?
26~ What side of the bed do you sleep on?
(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…)
11- What's your favorite restaurant? What’s your least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
50~ How many children do you have? What are their ages?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
44~ Care to share something about yourself that no one else knows about you?
53~ How much can you tell me about the one thing you are most passionate about?
Can you Deep Throat? Do you like the taste of yourself?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you 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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
I would allow you to do it… What would you do to me?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
If you win, what will you make them do?
Nothing too Serious
Doctor/Nurse Stripper/Client
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
51~ Are you willing to play adult games with your partner?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Would you ever want to be woken up with oral and/or intercourse?
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?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
49~ How many times have you been married? Why did they end?
76~ Have you had a threesome? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
Would you mind if your partner watched it? How about together vs alone?
7- What if a person smells a certain way? 8- How about smoking?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
82~ Do you have any fantasies involving Role-Playing?
45~ How do you feel about me blindfolding you? How about blindfolding me?
61~ How willing would you be to try new sexual positions?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
20- What’s your favorite candy? What’s your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
Have you ever? Care to Share?
The Ice Breaker Questions
Does the thought excite you? Care to share?
28- What are some things that people do that irritate you?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
92~ Have you ever had or have an STD? How many? What was it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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,
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
*** Questions about Relationships/Past ***
11~ Have you ever been caught by your parents or children or others while having sex?
9- If you could have three wishes, what would they be? Why?
How many partners have you had oral sex with? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Get this wrong and this could mean the end… :-) some funny, some not…
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
17- Have you ever done drugs? Which ones? How often?
Would you do it again, and would you rather 2 females or 2 males?
22- What is your favorite childhood memory? What is your least favorite?
2- What’s your favorite color? Do you a least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
How about if they talk dirty and/or call you names?
7- What are your thoughts on religion? Is there an afterlife?
Do you like it when they show and tell you what they want?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Escort/Client Job Applicant/Hiring Manager
19~ Who/when was your first “heartbreak”?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
10- List 5 of your top pet peeves.
Would you read them together?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
51~ What tends to bring a smile to your face?
17- What’s your favorite holiday? What’s your least favorite?
How well do you know me? And some of your thoughts about me
Master/Slave Boss/Maid
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Would you allow me to clean every part of your body with my soapy hands and fingers?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
If yes, what?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
1- What’s your favorite animal? Do you a least favorite?
12- What is the weirdest thing you've ever eaten?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
1~ How old were you when you had your first kiss? Who? 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…
How old are you? Male or Female?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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?
21~ What was the best date you ever went on? What has been the worst?
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?
19- What’s your favorite fairytale? What’s your least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
4- For a pet, Cat, dog or other?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Model/Photographer Police/Criminal
34~ Do you like the lights on or off during sex?
What have you learned about me that was new and/or surprising?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
39~ What are your love languages?
48~ Have you ever paid or been paid for sex?
If you say it, I will stop, and we can talk about it when you are ready.
What is your favorite toy? Ever wanted to try a specific toy?
Would /have you ever given your partner a lap dance and Striptease?
48~ Do you have any siblings? Are you close to your family?
92~ Everyone needs a “safe” word. What is yours?
What have you learned about yourself that you did not before this?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
7-What do I do in bed that drives you wild? How about, what turns you off?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Over time has your thoughts on sex changed?
18~ Who/when was your first “crush”?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
*** What’s Your Favorite…? ***
19- Do/have you smoked? What do you prefer? How often?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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)
Teacher/Student Stranger/One Night Stand
84~ How do you feel about reading/listening to adult stories?
If YES, was it with 2 men or 2 women? Did you enjoy it?
30~ What's something unexpected that turns you on?
Any that are a turn off?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3- What’s your favorite smell? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
42~ What’s your biggest regret in life?
36~ What is your favorite time of day to have sex/make love?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Repairman/Lonely Wife Virgin/Experienced
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
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?
29- How superstitious are you?
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?
65~ Describe the best orgasm you’ve ever had? Care to share?
67~ Do you like it when your partner moans and/or is vocal during sex?
That one or two things that made you go hmmmm, OMG or wow!
28~ What are some things that turn on? What is your biggest turn on?
18- How often do you drink alcohol? What is your favorite drink?
14- What's your favorite dessert? Do you a least favorite?
81~ Do you have any kinks and/or fetishes?
If NO, would you ever have one? Would it be with 2 men or 2 women?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
*** Random Questions ***
1- What was your first impression of me? Has it changed?
11- List at least 5 things on your bucket list. Have you done any of them already?
52~ What are your hobbies?
13- What is the craziest/scariest thing you've ever done?
33- Beach or Mountains? Or is there another place to like better?
How many times do you think you have “made love”?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Will you kiss after your partner has gone down on you? Swallow or spit semen?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
15~ Have you ever been “in love”? Who? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
*** Questions About Me ***
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
5~ When you first started having sex, was it what you thought it would be?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
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?
15- What bad habit do you wish you could quit? Do you have any addictions?
83~ How do you feel about Porn?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
What was the longest? What was the shortest?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
80~ Share your top three fantasies/desires. (Be detailed) 😊
8- What are your thoughts on politics?
47~ What would be your dream job and why?
33- If you could visit any time period, when would you pick? Please explain why?
Do you like the “69” position? Do you prefer to be on top or bottom?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Nurse/Patient Celebrity/Fan
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Do you watch it? What is your favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Do you have a favorite? Is it ok if your partner does?
25~ How do you feel about PDA? (Public Display of Affection)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
22- Do you have any birth marks? How about scars? Care to share how you got them?
37- Do you like your name? If you could change it, what would you change it too?
38~ Share your most embarrassing sexual memory?
What is your favorite position? Why?
71~ Would you give your partner a hand or foot job? Would you receive one?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
89~ Do you like taking showers together?
13~ Is there a difference between, making love, having sex, and fucking?
Any that are a turn off?
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?
32- What's your greatest talent? Can I see it right now?