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