What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 08:59
26~ What side of the bed do you sleep on?
Master/Slave Boss/Maid
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Why did my ex-narcissist move so fast with his new supply marriage engagement moving in, etc.?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
39~ What are your love languages?
15~ Have you ever been “in love”? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
62~ Have you used adult toys?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
How about if they talk dirty and/or call you names?
Have you ever been humiliated in front of a group of girls and enjoyed it?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
18- What’s your favorite way to relax after a long day? What’s your least favorite?
7- What if a person smells a certain way? 8- How about smoking?
Do you think Japan will have same-sex marriage by 2030?
11- What's your favorite restaurant? What’s your least favorite?
How well do you know me? And some of your thoughts about me
Prisoner/Prison Guard Landlord/Tenant
What symptoms did you notice before being diagnosed with cancer?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Nurse/Patient Celebrity/Fan
Why do some people tell the girl I like that I don’t like her when I do like her?
76~ Have you had a threesome? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
70~ Would/do you have/like anal sex?
80~ Share your top three fantasies/desires. (Be detailed) 😊
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
19- What’s your favorite fairytale? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
What is your daily motivation and does it work?
31- If given a chance to be immortal, would you take it? Why?
51~ What tends to bring a smile to your face?
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?
When will dating stop being so hard for Gen Z?
Will you cheat again? How can, you be sure? Define what cheating is to you.
48~ Have you ever paid or been paid for sex?
15- What's your favorite saying? What word or phrase is your least favorite?
28- What are some things that people do that irritate you?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Do you watch it? What is your favorite?
9- What’s your favorite season and why? What’s your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
*** Deal Breaker Questions ***
How old are you? Male or Female?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
12- What is the weirdest thing you've ever eaten?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Would /have you ever given your partner a lap dance and Striptease?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Family Relation Age Play
13- How about having a certain hair cut/style?
Do you like the “69” position? Do you prefer to be on top or bottom?
21~ What was the best date you ever went on? What has been the worst?
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Any that are a turn off?
36- Do you play video games? What is your favorite? Do you a least favorite?
Escort/Client Job Applicant/Hiring Manager
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Please share Did you stop?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
13- What is the craziest/scariest thing you've ever done?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
4- For a pet, Cat, dog or other?
82~ Do you have any fantasies involving Role-Playing?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
1~ How old were you when you had your first kiss? Who? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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…
33- Beach or Mountains? Or is there another place to like better?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What is your favorite position? Why?
21- What's your favorite way to spend a weekend or time off?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
52~ Are you willing to make “those types” of bets with your partner?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
5~ When you first started having sex, was it what you thought it would be?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
What would you say to prove to yourself that it was really you?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What have you learned about me that was new and/or surprising?
36~ What is your favorite time of day to have sex/make love?
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)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
(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…)
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,
How many partners have you had oral sex with? Who? Care to Share?
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?
47~ What would be your dream job and why?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
65~ Describe the best orgasm you’ve ever had? Care to share?
18~ Who/when was your first “crush”?
If you say it, I will stop, and we can talk about it when you are ready.
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What do you dislike about me? I asked you to be 100% honest.
42~ What’s your biggest regret in life?
1- What was your first impression of me? Has it changed?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
20- What’s your favorite candy? What’s your least favorite?
17- Have you ever done drugs? Which ones? How often?
The Ice Breaker Questions
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
89~ Do you like taking showers together?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Have you ever? Care to Share?
Do you think this brought you closer together?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Would you read them together?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
14- What's your favorite dessert? Do you a least favorite?
That one or two things that made you go hmmmm, OMG or wow!
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Do you have a favorite? Is it ok if your partner does?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
13~ Is there a difference between, making love, having sex, and fucking?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
3- Should Pluto still be considered a planet? 4- How about smoking?
3- What Superhero or Superpower would you want to be/have?
34- Ever been to a concert? What was your favorite? Who would you like to see?
34~ Do you like the lights on or off during sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
If NO, would you ever have one? Would it be with 2 men or 2 women?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
What have you learned about yourself that you did not before this?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
29~ What are some things that turn you off? What is your biggest turn off?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
3- What’s your favorite smell? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
11- How about if they like a certain sports team? 12-How about drinking too much?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Model/Photographer Police/Criminal
I would allow you to do it… What would you do to me?
Nothing too Serious
10- What is your favorite family tradition? What’s your least favorite?
Over time has your thoughts on sex changed?
67~ Do you like it when your partner moans and/or is vocal during sex?
Would you do it again, and would you rather 2 females or 2 males?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
12- What’s your favorite food? What’s your least favorite?
19- Do/have you smoked? What do you prefer? How often?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
11~ Have you ever been caught by your parents or children or others while having sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
18- How often do you drink alcohol? What is your favorite drink?
What was the longest? What was the shortest?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Do you like it when they show and tell you what they want?
83~ How do you feel about Porn?
Any that are a turn off?
9~ How many times over your lifetime do you think you have had sex so far?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
25~ How do you feel about PDA? (Public Display of Affection)
49~ How many times have you been married? Why did they end?
30~ What's something unexpected that turns you on?
10~ How many dates are necessary before you to have sex with someone?
Repairman/Lonely Wife Virgin/Experienced
2- What’s your favorite color? Do you a least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Would you mind if your partner watched it? How about together vs alone?
28~ What are some things that turn on? What is your biggest turn on?
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?
17- What’s your favorite holiday? What’s your least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
*** Questions About Me ***
10- List 5 of your top pet peeves.
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
44~ Care to share something about yourself that no one else knows about you?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
52~ What are your hobbies?
84~ How do you feel about reading/listening to adult stories?
9- If you could have three wishes, what would they be? Why?
71~ Would you give your partner a hand or foot job? Would you receive one?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
33- If you could visit any time period, when would you pick? Please explain why?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
48~ Do you have any siblings? Are you close to your family?
7-What do I do in bed that drives you wild? How about, what turns you off?
Would you ever want to be woken up with oral and/or intercourse?
Doctor/Nurse Stripper/Client
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?
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?
29- How superstitious are you?
If you win, what will you make them do?
13- What’s your favorite drink? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
You know that I will be 100% truthful, so ask.
11- List at least 5 things on your bucket list. Have you done any of them already?
60~ How important is oral sex? Do you like receiving? Do you like giving?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
* Give a rating for each one (0-100)
61~ How willing would you be to try new sexual positions?
What is your view on sex? Meaning, When/Where/ How often/
24~ What are your expectations in a relationship? (I know a very big question, take your time)
19~ Who/when was your first “heartbreak”?
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
1- What’s your favorite animal? Do you a least favorite?
If yes, what?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Does the thought excite you? Care to share?
Get this wrong and this could mean the end… :-) some funny, some not…
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
40~ What’s the weirdest place you’ve ever had sex?
Can you Deep Throat? Do you like the taste of yourself?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Teacher/Student Stranger/One Night Stand
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
81~ Do you have any kinks and/or fetishes?
22- What is your favorite childhood memory? What is your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
15- What bad habit do you wish you could quit? Do you have any addictions?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
*** Random Questions ***
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
32- What's your greatest talent? Can I see it right now?
51~ Are you willing to play adult games with your partner?
37- Do you like your name? If you could change it, what would you change it too?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
How many times do you think you have “made love”?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
23- What is your dream job? What was it as a child?
92~ Have you ever had or have an STD? How many? What was it?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
*** What’s Your Favorite…? ***
50~ How many children do you have? What are their ages?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
*** Questions about Relationships/Past ***
8- What are your thoughts on politics?
7- What are your thoughts on religion? Is there an afterlife?