What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 09:48
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Why am I sweating so much at night even though my room is really cold?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
80~ Share your top three fantasies/desires. (Be detailed) 😊
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
What a list actors/ actresses are notorious for being jerks in real life?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Can you Deep Throat? Do you like the taste of yourself?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Why did Obito, a supposed "bad person," do good things for Kakashi?
92~ Have you ever had or have an STD? How many? What was it?
50~ How many children do you have? What are their ages?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
(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…)
Will you cheat again? How can, you be sure? Define what cheating is to you.
Would you ever want to be woken up with oral and/or intercourse?
Have you ever accidentally found out that you were about to be fired?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
15- What's your favorite saying? What word or phrase is your least favorite?
47~ What would be your dream job and why?
Why do Democrats never produce a good argument for why Trump was a bad president?
34~ Do you like the lights on or off during sex?
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)
Who was the guy that had sex with the AIDS monkey?
22- Do you have any birth marks? How about scars? Care to share how you got them?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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?
Will you share your wife? Can she take both of us at the same time?
28- What are some things that people do that irritate you?
What is your view on sex? Meaning, When/Where/ How often/
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?
Why do Muslims not get HIV/AIDS in spite of having 4 wives and multiple relationships?
52~ Are you willing to make “those types” of bets with your partner?
Teacher/Student Stranger/One Night Stand
51~ What tends to bring a smile to your face?
2- What’s your favorite color? Do you a least favorite?
Would you mind if your partner watched it? How about together vs alone?
48~ Have you ever paid or been paid for sex?
Why are daughters mean to their mothers?
21~ What was the best date you ever went on? What has been the worst?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
15- What bad habit do you wish you could quit? Do you have any addictions?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
70~ Would/do you have/like anal sex?
10~ How many dates are necessary before you to have sex with someone?
11- List at least 5 things on your bucket list. Have you done any of them already?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
29- How superstitious are you?
Doctor/Nurse Stripper/Client
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?
How about if they talk dirty and/or call you names?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
25~ How do you feel about PDA? (Public Display of Affection)
12- What’s your favorite food? What’s your least favorite?
39~ What are your love languages?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
40~ What’s the weirdest place you’ve ever had sex?
What is your favorite toy? Ever wanted to try a specific toy?
3- What’s your favorite smell? Do you a least favorite?
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?
How many times do you think you have “made love”?
27- What was/ is nickname? Does it have a meaning behind it?
Model/Photographer Police/Criminal
11~ Have you ever been caught by your parents or children or others while having sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
81~ Do you have any kinks and/or fetishes?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Do you like it when they show and tell you what they want?
What is your favorite position? Why?
18- How often do you drink alcohol? What is your favorite drink?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
23- What is your dream job? What was it as a child?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
If you win, what will you make them do?
20- What’s your favorite candy? What’s your least 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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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,
51~ Are you willing to play adult games with your partner?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
45~ How do you feel about me blindfolding you? How about blindfolding me?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
82~ Do you have any fantasies involving Role-Playing?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
*** Questions About Me ***
Would you allow me to clean every part of your body with my soapy hands and fingers?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
7- What if a person smells a certain way? 8- How about smoking?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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…
9- If you could have three wishes, what would they be? Why?
Family Relation Age Play
5- Have you ever been hypnotized? Would you allow yourself to be?
11- What's your favorite restaurant? What’s your least favorite?
*** What’s Your Favorite…? ***
13~ Is there a difference between, making love, having sex, and fucking?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
15~ Have you ever been “in love”? Who? Care to Share?
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?
If yes, what?
The Ice Breaker Questions
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What was the longest? What was the shortest?
Prisoner/Prison Guard Landlord/Tenant
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
11- How about if they like a certain sports team? 12-How about drinking too much?
How many partners have you had oral sex with? Who? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Any that are a turn off?
76~ Have you had a threesome? Care to Share?
12- What is the weirdest thing you've ever eaten?
36- Do you play video games? What is your favorite? Do you a least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
89~ Do you like taking showers together?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
84~ How do you feel about reading/listening to adult stories?
13- What’s your favorite drink? What’s your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
4- For a pet, Cat, dog or other?
83~ How do you feel about Porn?
19- Do/have you smoked? What do you prefer? How often?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
21- What's your favorite way to spend a weekend or time off?
49~ How many times have you been married? Why did they end?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
32- What's your greatest talent? Can I see it right now?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
31- If given a chance to be immortal, would you take it? Why?
7-What do I do in bed that drives you wild? How about, what turns you off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you have a favorite? Is it ok if your partner does?
*** Random Questions ***
*** Questions about Relationships/Past ***
6- Do you have dreams? Can you remember them? What do you usually dream about?
What have you learned about me that was new and/or surprising?
22- What is your favorite childhood memory? What is your least favorite?
You know that I will be 100% truthful, so ask.
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7- What are your thoughts on religion? Is there an afterlife?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
That one or two things that made you go hmmmm, OMG or wow!
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
1- What was your first impression of me? Has it changed?
Would you do it again, and would you rather 2 females or 2 males?
19- What’s your favorite fairytale? What’s your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Do you think this brought you closer together?
13- What is the craziest/scariest thing you've ever done?
18~ Who/when was your first “crush”?
92~ Everyone needs a “safe” word. What is yours?
14- What's your favorite dessert? Do you a least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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…
52~ What are your hobbies?
44~ Care to share something about yourself that no one else knows about you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Escort/Client Job Applicant/Hiring Manager
10- List 5 of your top pet peeves.
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
36~ What is your favorite time of day to have sex/make love?
9~ How many times over your lifetime do you think you have had sex so far?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
How old are you? Male or Female?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
If YES, was it with 2 men or 2 women? Did you enjoy it?
If NO, would you ever have one? Would it be with 2 men or 2 women?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
Does the thought excite you? Care to share?
10- What is your favorite family tradition? What’s your least favorite?
Over time has your thoughts on sex changed?
60~ How important is oral sex? Do you like receiving? Do you like giving?
* Give a rating for each one (0-100)
48~ Do you have any siblings? Are you close to your family?
Any that are a turn off?
42~ What’s your biggest regret in life?
19~ Who/when was your first “heartbreak”?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
62~ Have you used adult toys?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
*** Deal Breaker Questions ***
71~ Would you give your partner a hand or foot job? Would you receive one?
67~ Do you like it when your partner moans and/or is vocal during sex?
1~ How old were you when you had your first kiss? Who? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
What would you say to prove to yourself that it was really you?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
14- What is an embarrassing moment in your life? How about your most embarrassing?
33- If you could visit any time period, when would you pick? Please explain why?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
3- What Superhero or Superpower would you want to be/have?
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
61~ How willing would you be to try new sexual positions?
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
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Nothing too Serious
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?
If you say it, I will stop, and we can talk about it when you are ready.
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
37- Do you like your name? If you could change it, what would you change it too?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
13- How about having a certain hair cut/style?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What do you dislike about me? I asked you to be 100% honest.
28~ What are some things that turn on? What is your biggest turn on?
17- Have you ever done drugs? Which ones? How often?
53~ How much can you tell me about the one thing you are most passionate about?
I would allow you to do it… What would you do to me?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
30~ What's something unexpected that turns you on?
8- What are your thoughts on politics?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
Do you watch it? What is your favorite?
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?
Would /have you ever given your partner a lap dance and Striptease?
38~ Share your most embarrassing sexual memory?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Master/Slave Boss/Maid
Please share Did you stop?
How well do you know me? And some of your thoughts about me
18- What’s your favorite way to relax after a long day? 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?
1- What’s your favorite animal? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
33- Beach or Mountains? Or is there another place to like better?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
17- What’s your favorite holiday? What’s your least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
26~ What side of the bed do you sleep on?
5~ When you first started having sex, was it what you thought it would be?
Have you ever? Care to Share?