What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 16:24
I would allow you to do it… What would you do to me?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
40~ What’s the weirdest place you’ve ever had sex?
Why is Nickelback known to be a bad band?
37- Do you like your name? If you could change it, what would you change it too?
52~ What are your hobbies?
30~ What's something unexpected that turns you on?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Does the thought excite you? Care to share?
What smell will you never forget?
22- What is your favorite childhood memory? What is your least favorite?
What would you say to prove to yourself that it was really you?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
If a cat is feminine in German, what article do you give to a male cat?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Have you ever secretly watched someone while they were doing something private?
1~ How old were you when you had your first kiss? Who? Care to Share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
50~ How many children do you have? What are their ages?
How did Nickelback gain a large fan base despite criticism of their music?
Would you ever want to be woken up with oral and/or intercourse?
62~ Have you used adult toys?
61~ How willing would you be to try new sexual positions?
What does it mean to you to live a life that reflects biblical values?
32- What's your greatest talent? Can I see it right now?
60~ How important is oral sex? Do you like receiving? Do you like giving?
How many times do you think you have “made love”?
82~ Do you have any fantasies involving Role-Playing?
10- What is your favorite family tradition? What’s your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
19- Do/have you smoked? What do you prefer? How often?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Escort/Client Job Applicant/Hiring Manager
Why are black women the largest unmarried group in the United States of America?
12- What’s your favorite food? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
38~ Share your most embarrassing sexual memory?
17- What’s your favorite holiday? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What have you learned about yourself that you did not before this?
15~ Have you ever been “in love”? Who? Care to Share?
*** Questions about Relationships/Past ***
3- What was the most surprising thing you’ve learned about me throughout our relationship?
8- What's your favorite flavor of ice cream? Do you a least favorite?
How old are you? Male or Female?
*** Deal Breaker Questions ***
89~ Do you like taking showers together?
What have you learned about me that was new and/or surprising?
22- Do you have any birth marks? How about scars? Care to share how you got them?
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- What is an embarrassing moment in your life? How about your most embarrassing?
7-What do I do in bed that drives you wild? How about, what turns you off?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
If yes, what?
Can you Deep Throat? Do you like the taste of yourself?
28~ What are some things that turn on? What is your biggest turn on?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
15- What's your favorite saying? What word or phrase is your least favorite?
36~ What is your favorite time of day to have sex/make love?
11~ Have you ever been caught by your parents or children or others while having sex?
47~ What would be your dream job and why?
10- List 5 of your top pet peeves.
Would you do it again, and would you rather 2 females or 2 males?
76~ Have you had a threesome? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
9- What’s your favorite season and why? What’s your least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Any that are a turn off?
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?
17- Have you ever done drugs? Which ones? How often?
Get this wrong and this could mean the end… :-) some funny, some not…
9- Is there something you’ve always wanted to ask me but you’re afraid?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Any that are a turn off?
Do you think this brought you closer together?
Will you cheat again? How can, you be sure? Define what cheating is to you.
42~ What’s your biggest regret in life?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
4- For a pet, Cat, dog or other?
21~ What was the best date you ever went on? What has been the worst?
Would you mind if your partner watched it? How about together vs alone?
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?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
70~ Would/do you have/like anal sex?
2- What’s your favorite color? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
20- What’s your favorite candy? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
13- What is the craziest/scariest thing you've ever done?
What is your favorite toy? Ever wanted to try a specific toy?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
19~ Who/when was your first “heartbreak”?
7- What are your thoughts on religion? Is there an afterlife?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
If YES, was it with 2 men or 2 women? Did you enjoy it?
(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- List at least 5 things on your bucket list. Have you done any of them already?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
51~ What tends to bring a smile to your face?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
18~ Who/when was your first “crush”?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? 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,
How many partners have you had oral sex with? Who? Care to Share?
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?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Do you like the “69” position? Do you prefer to be on top or bottom?
Nothing too Serious
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
67~ Do you like it when your partner moans and/or is vocal during sex?
Doctor/Nurse Stripper/Client
*** Random Questions ***
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
12- What is the weirdest thing you've ever eaten?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What is your view on sex? Meaning, When/Where/ How often/
If you win, what will you make them do?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
71~ Would you give your partner a hand or foot job? Would you receive one?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
*** What’s Your Favorite…? ***
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
19- What’s your favorite fairytale? What’s your least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
11- How about if they like a certain sports team? 12-How about drinking too much?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
33- If you could visit any time period, when would you pick? Please explain why?
1- What’s your favorite animal? Do you a least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Have you ever? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Family Relation Age Play
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
83~ How do you feel about Porn?
Do you have a favorite? Is it ok if your partner does?
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?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Model/Photographer Police/Criminal
48~ Have you ever paid or been paid for sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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)
5~ When you first started having sex, was it what you thought it would be?
*** Questions About Me ***
31- If given a chance to be immortal, would you take it? Why?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
1- What was your first impression of me? Has it changed?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Do you watch it? What is your favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
3- What’s your favorite smell? Do you a least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
84~ How do you feel about reading/listening to adult stories?
What was the longest? What was the shortest?
5- Have you ever been hypnotized? Would you allow yourself to be?
What is your favorite position? Why?
25~ How do you feel about PDA? (Public Display of Affection)
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
14- What's your favorite dessert? Do you a least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
Would /have you ever given your partner a lap dance and Striptease?
13~ Is there a difference between, making love, having sex, and fucking?
13- How about having a certain hair cut/style?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
You know that I will be 100% truthful, so ask.
26~ What side of the bed do you sleep on?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
29~ What are some things that turn you off? What is your biggest turn off?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Prisoner/Prison Guard Landlord/Tenant
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
9~ How many times over your lifetime do you think you have had sex so far?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
11- What's your favorite restaurant? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
23- What is your dream job? What was it as a child?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
3- What Superhero or Superpower would you want to be/have?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
49~ How many times have you been married? Why did they end?
How about if they talk dirty and/or call you names?
18- How often do you drink alcohol? What is your favorite drink?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
36- Do you play video games? What is your favorite? Do you a least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
The Ice Breaker Questions
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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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…
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
65~ Describe the best orgasm you’ve ever had? Care to share?
If you say it, I will stop, and we can talk about it when you are ready.
Nurse/Patient Celebrity/Fan
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
92~ Have you ever had or have an STD? How many? What was it?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
53~ How much can you tell me about the one thing you are most passionate about?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Teacher/Student Stranger/One Night Stand
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
10~ How many dates are necessary before you to have sex with someone?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you like it when they show and tell you what they want?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
48~ Do you have any siblings? Are you close to your family?
Would you read them together?
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.?
* Give a rating for each one (0-100)
9- If you could have three wishes, what would they be? Why?
What do you dislike about me? I asked you to be 100% honest.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
92~ Everyone needs a “safe” word. What is yours?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
44~ Care to share something about yourself that no one else knows about you?
Would you allow me to clean every part of your body with my soapy hands and fingers?
34~ Do you like the lights on or off during sex?
Repairman/Lonely Wife Virgin/Experienced
51~ Are you willing to play adult games with your partner?
80~ Share your top three fantasies/desires. (Be detailed) 😊
7- What if a person smells a certain way? 8- How about smoking?
Please share Did you stop?
Over time has your thoughts on sex changed?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
29- How superstitious are you?
13- What’s your favorite drink? What’s your least favorite?
8- What are your thoughts on politics?
28- What are some things that people do that irritate you?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
That one or two things that made you go hmmmm, OMG or wow!
Master/Slave Boss/Maid