What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 05:31
21~ What was the best date you ever went on? What has been the worst?
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?
10- List 5 of your top pet peeves.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
9~ How many times over your lifetime do you think you have had sex so far?
If yes, what?
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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?
Get this wrong and this could mean the end… :-) some funny, some not…
20- What’s your favorite candy? What’s your least favorite?
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Prisoner/Prison Guard Landlord/Tenant
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
If you win, what will you make them do?
What are effective strategies to build a referral network for BPO projects?
If YES, was it with 2 men or 2 women? Did you enjoy it?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
What ended your relationship with your best friend?
11- How about if they like a certain sports team? 12-How about drinking too much?
Do you think this brought you closer together?
Teacher/Student Stranger/One Night Stand
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44~ Care to share something about yourself that no one else knows about you?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
36~ What is your favorite time of day to have sex/make love?
53~ How much can you tell me about the one thing you are most passionate about?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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Do you watch it? What is your favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
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4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
If you say it, I will stop, and we can talk about it when you are ready.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
How many times do you think you have “made love”?
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67~ Do you like it when your partner moans and/or is vocal during sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
How can I have an overnight glow-up for school?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Any that are a turn off?
25~ How do you feel about PDA? (Public Display of Affection)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
The Ice Breaker Questions
Will you cheat again? How can, you be sure? Define what cheating is to you.
29~ What are some things that turn you off? What is your biggest turn off?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
15~ Have you ever been “in love”? Who? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
30~ What's something unexpected that turns you on?
* Give a rating for each one (0-100)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
12- What is the weirdest thing you've ever eaten?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Model/Photographer Police/Criminal
51~ What tends to bring a smile to your face?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
52~ What are your hobbies?
Nothing too Serious
1- What’s your favorite animal? Do you a least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
17- Have you ever done drugs? Which ones? How often?
65~ Describe the best orgasm you’ve ever had? Care to share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
I would allow you to do it… What would you do to me?
80~ Share your top three fantasies/desires. (Be detailed) 😊
How about if they talk dirty and/or call you names?
1- What was your first impression of me? Has it changed?
50~ How many children do you have? What are their ages?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
92~ Everyone needs a “safe” word. What is yours?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
38~ Share your most embarrassing sexual memory?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
If NO, would you ever have one? Would it be with 2 men or 2 women?
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,
12- What’s your favorite food? What’s your least favorite?
9- What’s your favorite season and why? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
*** Deal Breaker Questions ***
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
1~ How old were you when you had your first kiss? Who? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
14- What is an embarrassing moment in your life? How about your most embarrassing?
7- What if a person smells a certain way? 8- How about smoking?
13- What is the craziest/scariest thing you've ever done?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
3- What’s your favorite smell? Do you a least favorite?
5~ When you first started having sex, was it what you thought it would be?
6- Do you have dreams? Can you remember them? What do you usually dream about?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Please share Did you stop?
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?
3- Should Pluto still be considered a planet? 4- How about smoking?
60~ How important is oral sex? Do you like receiving? Do you like giving?
13- What’s your favorite drink? What’s your least favorite?
*** What’s Your Favorite…? ***
What is your favorite toy? Ever wanted to try a specific toy?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Would you mind if your partner watched it? How about together vs alone?
Have you ever? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
29- How superstitious are you?
4- For a pet, Cat, dog or other?
22- What is your favorite childhood memory? What is your least favorite?
76~ Have you had a threesome? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
15- What bad habit do you wish you could quit? Do you have any addictions?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
81~ Do you have any kinks and/or fetishes?
47~ What would be your dream job and why?
21- What's your favorite way to spend a weekend or time off?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
39~ What are your love languages?
33- Beach or Mountains? Or is there another place to like better?
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?
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?
(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…)
49~ How many times have you been married? Why did they end?
2- What’s your favorite color? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
26~ What side of the bed do you sleep on?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What is your view on sex? Meaning, When/Where/ How often/
*** Questions About Me ***
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would /have you ever given your partner a lap dance and Striptease?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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?
*** Random Questions ***
7- What are your thoughts on religion? Is there an afterlife?
*** Questions about Relationships/Past ***
Do you like the “69” position? Do you prefer to be on top or bottom?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
9- If you could have three wishes, what would they be? Why?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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?
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…
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
36- Do you play video games? What is your favorite? Do you a least favorite?
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71~ Would you give your partner a hand or foot job? Would you receive one?
Does the thought excite you? Care to share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
31- If given a chance to be immortal, would you take it? Why?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
8- What are your thoughts on politics?
7-What do I do in bed that drives you wild? How about, what turns you off?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Any that are a turn off?
37- Do you like your name? If you could change it, what would you change it too?
How well do you know me? And some of your thoughts about me
11- List at least 5 things on your bucket list. Have you done any of them already?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
13- How about having a certain hair cut/style?
19~ Who/when was your first “heartbreak”?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
17- What’s your favorite holiday? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
42~ What’s your biggest regret in life?
Do you like it when they show and tell you what they want?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What do you dislike about me? I asked you to be 100% honest.
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
What would you say to prove to yourself that it was really you?
62~ Have you used adult toys?
33- If you could visit any time period, when would you pick? Please explain why?
10~ How many dates are necessary before you to have sex with someone?
Can you Deep Throat? Do you like the taste of yourself?
18~ Who/when was your first “crush”?
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…
8- What's your favorite flavor of ice cream? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
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?
61~ How willing would you be to try new sexual positions?
Escort/Client Job Applicant/Hiring Manager
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
48~ Do you have any siblings? Are you close to your family?
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?
Would you read them together?
Doctor/Nurse Stripper/Client
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
You know that I will be 100% truthful, so ask.
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
92~ Have you ever had or have an STD? How many? What was it?
Repairman/Lonely Wife Virgin/Experienced
28- What are some things that people do that irritate you?
51~ Are you willing to play adult games with your partner?
5- Have you ever been hypnotized? Would you allow yourself to be?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
How old are you? Male or Female?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
83~ How do you feel about Porn?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
11~ Have you ever been caught by your parents or children or others while having sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Nurse/Patient Celebrity/Fan
13~ Is there a difference between, making love, having sex, and fucking?
18- How often do you drink alcohol? What is your favorite drink?
89~ Do you like taking showers together?
82~ Do you have any fantasies involving Role-Playing?
How many partners have you had oral sex with? Who? Care to Share?
Over time has your thoughts on sex changed?
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 have you learned about yourself that you did not before this?
84~ How do you feel about reading/listening to adult stories?
Master/Slave Boss/Maid
3- What Superhero or Superpower would you want to be/have?
What is your favorite position? Why?
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- What is your favorite family tradition? What’s your least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
48~ Have you ever paid or been paid for sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
What was the longest? What was the shortest?
Would you ever want to be woken up with oral and/or intercourse?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Would you do it again, and would you rather 2 females or 2 males?
What have you learned about me that was new and/or surprising?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
70~ Would/do you have/like anal sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
23- What is your dream job? What was it as a child?
28~ What are some things that turn on? What is your biggest turn on?
34~ Do you like the lights on or off during sex?
32- What's your greatest talent? Can I see it right now?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
14- What's your favorite dessert? Do you a least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Family Relation Age Play
Do you have a favorite? Is it ok if your partner does?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?