What is the most interesting question you can ask to get to know someone?
Last Updated: 26.06.2025 00:24
Would you ever want to be woken up with oral and/or intercourse?
*** Random Questions ***
1~ How old were you when you had your first kiss? Who? Care to Share?
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73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Is a man over 50 not married no kids a red flag?
What is your favorite position? Why?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Nothing too Serious
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9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
You know that I will be 100% truthful, so ask.
2- What’s your favorite color? Do you a least favorite?
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4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Please share Did you stop?
Why don't some people like the 10 Commandments?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
39~ What are your love languages?
If you say it, I will stop, and we can talk about it when you are ready.
52~ What are your hobbies?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What goes into writing a great movie script?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
26~ What side of the bed do you sleep on?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
What was it like being spanked as a kid?
7-What do I do in bed that drives you wild? How about, what turns you off?
71~ Would you give your partner a hand or foot job? Would you receive one?
Have you ever? Care to Share?
Why do I feel so tired all the time even after a good night’s sleep?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
53~ How much can you tell me about the one thing you are most passionate about?
What was the longest? What was the shortest?
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27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
52~ Are you willing to make “those types” of bets with your partner?
30~ What's something unexpected that turns you on?
61~ How willing would you be to try new sexual positions?
12- What’s your favorite food? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
9- If you could have three wishes, what would they be? Why?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
28~ What are some things that turn on? What is your biggest turn on?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
22- What is your favorite childhood memory? What is your least favorite?
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
19- Do/have you smoked? What do you prefer? How often?
36- Do you play video games? What is your favorite? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
29~ What are some things that turn you off? What is your biggest turn off?
What have you learned about me that was new and/or surprising?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
*** What’s Your Favorite…? ***
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
What have you learned about yourself that you did not before this?
*** Questions about Relationships/Past ***
12- What is the weirdest thing you've ever eaten?
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?
10~ How many dates are necessary before you to have sex with someone?
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…
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)
3- What’s your favorite smell? Do you a least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
21~ What was the best date you ever went on? What has been the worst?
28- What are some things that people do that irritate you?
Over time has your thoughts on sex changed?
83~ How do you feel about Porn?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
33- Beach or Mountains? Or is there another place to like better?
Doctor/Nurse Stripper/Client
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
80~ Share your top three fantasies/desires. (Be detailed) 😊
84~ How do you feel about reading/listening to adult stories?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Would /have you ever given your partner a lap dance and Striptease?
13- What is the craziest/scariest thing you've ever done?
*** Questions About Me ***
17- Have you ever done drugs? Which ones? How often?
Nurse/Patient Celebrity/Fan
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Would you do it again, and would you rather 2 females or 2 males?
Would you mind if your partner watched it? How about together vs alone?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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…
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
The Ice Breaker Questions
92~ Everyone needs a “safe” word. What is yours?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
What would you say to prove to yourself that it was really you?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Does the thought excite you? Care to share?
17- What’s your favorite holiday? What’s your least favorite?
Family Relation Age Play
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
33- If you could visit any time period, when would you pick? Please explain why?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
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,
9- Is there something you’ve always wanted to ask me but you’re afraid?
76~ Have you had a threesome? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
67~ Do you like it when your partner moans and/or is vocal during sex?
Model/Photographer Police/Criminal
31- If given a chance to be immortal, would you take it? Why?
What is your favorite toy? Ever wanted to try a specific toy?
If YES, was it with 2 men or 2 women? Did you enjoy it?
5- Have you ever been hypnotized? Would you allow yourself to be?
(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…)
27- What was/ is nickname? Does it have a meaning behind it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
21- What's your favorite way to spend a weekend or time off?
6- Do you have dreams? Can you remember them? What do you usually dream about?
81~ Do you have any kinks and/or fetishes?
11- How about if they like a certain sports team? 12-How about drinking too much?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
18- How often do you drink alcohol? What is your favorite drink?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Prisoner/Prison Guard Landlord/Tenant
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Do you watch it? What is your favorite?
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?
Can you Deep Throat? Do you like the taste of yourself?
5~ When you first started having sex, was it what you thought it would be?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
51~ Are you willing to play adult games with your partner?
25~ How do you feel about PDA? (Public Display of Affection)
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
Do you have a favorite? Is it ok if your partner does?
11- What's your favorite restaurant? What’s your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
How about if they talk dirty and/or call you names?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
4- For a pet, Cat, dog or other?
82~ Do you have any fantasies involving Role-Playing?
20- What’s your favorite candy? What’s your least favorite?
34~ Do you like the lights on or off during sex?
I would allow you to do it… What would you do to me?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you like it when they show and tell you what they want?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
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?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
11~ Have you ever been caught by your parents or children or others while having sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What do you dislike about me? I asked you to be 100% honest.
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?
37- Do you like your name? If you could change it, what would you change it too?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
15- What's your favorite saying? What word or phrase is your least favorite?
18~ Who/when was your first “crush”?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
13- How about having a certain hair cut/style?
How many times do you think you have “made love”?
7- What if a person smells a certain way? 8- How about smoking?
Teacher/Student Stranger/One Night Stand
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
How well do you know me? And some of your thoughts about me
48~ Do you have any siblings? Are you close to your family?
65~ Describe the best orgasm you’ve ever had? Care to share?
23- What is your dream job? What was it as a child?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Any that are a turn off?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
11- List at least 5 things on your bucket list. Have you done any of them already?
If you win, what will you make them do?
1- What’s your favorite animal? Do you a least favorite?
Master/Slave Boss/Maid
* Give a rating for each one (0-100)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
38~ Share your most embarrassing sexual memory?
How old are you? Male or Female?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
7- What are your thoughts on religion? Is there an afterlife?
62~ Have you used adult toys?
44~ Care to share something about yourself that no one else knows about you?
32- What's your greatest talent? Can I see it right now?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
14- What's your favorite dessert? Do you a least favorite?
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?
92~ Have you ever had or have an STD? How many? What was it?
10- List 5 of your top pet peeves.
Any that are a turn off?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
What is your view on sex? Meaning, When/Where/ How often/
3- What Superhero or Superpower would you want to be/have?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
If NO, would you ever have one? Would it be with 2 men or 2 women?
22- Do you have any birth marks? How about scars? Care to share how you got them?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
9- What’s your favorite season and why? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Do you like the “69” position? Do you prefer to be on top or bottom?
1- What was your first impression of me? Has it changed?
50~ How many children do you have? What are their ages?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
19- What’s your favorite fairytale? What’s your least favorite?
If yes, what?
70~ Would/do you have/like anal sex?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
18- What’s your favorite way to relax after a long day? What’s your least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
47~ What would be your dream job and why?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Would you read them together?
Escort/Client Job Applicant/Hiring Manager
*** Deal Breaker Questions ***
48~ Have you ever paid or been paid for sex?
42~ What’s your biggest regret in life?
19~ Who/when was your first “heartbreak”?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
89~ Do you like taking showers together?
8- What are your thoughts on politics?
That one or two things that made you go hmmmm, OMG or wow!
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Do you think this brought you closer together?
Get this wrong and this could mean the end… :-) some funny, some not…
49~ How many times have you been married? Why did they end?
How many partners have you had oral sex with? Who? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
34- Ever been to a concert? What was your favorite? Who would you like to see?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
29- How superstitious are you?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
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?
36~ What is your favorite time of day to have sex/make love?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?