What is the most interesting question you can ask to get to know someone?
11.06.2025 04:43
5~ When you first started having sex, was it what you thought it would be?
Will you cheat again? How can, you be sure? Define what cheating is to you.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Do crossdressers like wearing pantyliners and tampons in their butts?
15- What's your favorite saying? What word or phrase is your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Would you ever want to be woken up with oral and/or intercourse?
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69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Would /have you ever given your partner a lap dance and Striptease?
Why is every human messed up in some way?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Teacher/Student Stranger/One Night Stand
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,
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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)
36- Do you play video games? What is your favorite? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
FDA grants limited approval to new Covid vaccine from Moderna - NBC News
How many partners have you had oral sex with? Who? Care to Share?
Master/Slave Boss/Maid
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Overthinking is killing me day-by-day. What should I do?
How well do you know me? And some of your thoughts about me
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
8- What are your thoughts on politics?
People’s Pharmacy: Did this OTC allergy medicine cause my excruciating knee pain? - OregonLive.com
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What is your favorite position? Why?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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29~ What are some things that turn you off? What is your biggest turn off?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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…
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Do you watch it? What is your favorite?
How about if they talk dirty and/or call you names?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Over time has your thoughts on sex changed?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What happened to The Simpsons deleted onscreen footage?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
33- Beach or Mountains? Or is there another place to like better?
10~ How many dates are necessary before you to have sex with someone?
1- What was your first impression of me? Has it changed?
What was the longest? What was the shortest?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What do you dislike about me? I asked you to be 100% honest.
17- What’s your favorite holiday? What’s your least favorite?
31- If given a chance to be immortal, would you take it? Why?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
18- How often do you drink alcohol? What is your favorite drink?
67~ Do you like it when your partner moans and/or is vocal during sex?
84~ How do you feel about reading/listening to adult stories?
12- What is the weirdest thing you've ever eaten?
52~ Are you willing to make “those types” of bets with your partner?
47~ What would be your dream job and why?
92~ Have you ever had or have an STD? How many? What was it?
10- List 5 of your top pet peeves.
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
7- What if a person smells a certain way? 8- How about smoking?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you like the “69” position? Do you prefer to be on top or bottom?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
53~ How much can you tell me about the one thing you are most passionate about?
18- What’s your favorite way to relax after a long day? 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…
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
51~ What tends to bring a smile to your face?
14- What's your favorite dessert? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
18~ Who/when was your first “crush”?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Would you allow me to clean every part of your body with my soapy hands and fingers?
3- What Superhero or Superpower would you want to be/have?
*** Questions about Relationships/Past ***
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
I would allow you to do it… What would you do to me?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
If NO, would you ever have one? Would it be with 2 men or 2 women?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Does the thought excite you? Care to share?
13~ Is there a difference between, making love, having sex, and fucking?
50~ How many children do you have? What are their ages?
62~ Have you used adult toys?
52~ What are your hobbies?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
11- What's your favorite restaurant? What’s your least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
33- If you could visit any time period, when would you pick? Please explain why?
11- How about if they like a certain sports team? 12-How about drinking too much?
9- Is there something you’ve always wanted to ask me but you’re afraid?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
27- What was/ is nickname? Does it have a meaning behind it?
Have you ever? Care to Share?
4- For a pet, Cat, dog or other?
32- What's your greatest talent? Can I see it right now?
51~ Are you willing to play adult games with your partner?
Do you like it when they show and tell you what they want?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
*** Questions About Me ***
What is your favorite toy? Ever wanted to try a specific toy?
38~ Share your most embarrassing sexual memory?
* Give a rating for each one (0-100)
60~ How important is oral sex? Do you like receiving? Do you like giving?
19- Do/have you smoked? What do you prefer? How often?
9- If you could have three wishes, what would they be? Why?
81~ Do you have any kinks and/or fetishes?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
5- Have you ever been hypnotized? Would you allow yourself to be?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
9- What’s your favorite season and why? What’s your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
9~ How many times over your lifetime do you think you have had sex so far?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
80~ Share your top three fantasies/desires. (Be detailed) 😊
13- How about having a certain hair cut/style?
That one or two things that made you go hmmmm, OMG or wow!
71~ Would you give your partner a hand or foot job? Would you receive one?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Model/Photographer Police/Criminal
Can you Deep Throat? Do you like the taste of yourself?
11~ Have you ever been caught by your parents or children or others while having sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
42~ What’s your biggest regret in life?
20- What’s your favorite candy? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
48~ Have you ever paid or been paid for sex?
How old are you? Male or Female?
11- List at least 5 things on your bucket list. Have you done any of them already?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Any that are a turn off?
*** Random Questions ***
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
29- How superstitious are you?
Would you read them together?
1~ How old were you when you had your first kiss? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
*** What’s Your Favorite…? ***
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
7- What are your thoughts on religion? Is there an afterlife?
*** Deal Breaker Questions ***
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Family Relation Age Play
Doctor/Nurse Stripper/Client
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
36~ What is your favorite time of day to have sex/make love?
30~ What's something unexpected that turns you on?
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)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
26~ What side of the bed do you sleep on?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
13- What’s your favorite drink? 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…
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
13- What is the craziest/scariest thing you've ever done?
76~ Have you had a threesome? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
How many times do you think you have “made love”?
Get this wrong and this could mean the end… :-) some funny, some not…
39~ What are your love languages?
28- What are some things that people do that irritate you?
2- What’s your favorite color? Do you a least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
You know that I will be 100% truthful, so ask.
Escort/Client Job Applicant/Hiring Manager
40~ What’s the weirdest place you’ve ever had sex?
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
10- What is your favorite family tradition? What’s your least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
83~ How do you feel about Porn?
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?
21- What's your favorite way to spend a weekend or time off?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
44~ Care to share something about yourself that no one else knows about you?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Nothing too Serious
25~ How do you feel about PDA? (Public Display of Affection)
If you win, what will you make them do?
Nurse/Patient Celebrity/Fan
28~ What are some things that turn on? What is your biggest turn on?
23- What is your dream job? What was it as a child?
What have you learned about me that was new and/or surprising?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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?
Prisoner/Prison Guard Landlord/Tenant
1- What’s your favorite animal? Do you a least favorite?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Please share Did you stop?
If you say it, I will stop, and we can talk about it when you are ready.
3- What’s your favorite smell? Do you a least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
34~ Do you like the lights on or off during sex?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
70~ Would/do you have/like anal sex?
Any that are a turn off?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
82~ Do you have any fantasies involving Role-Playing?
65~ Describe the best orgasm you’ve ever had? Care to share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
What would you say to prove to yourself that it was really you?
Would you mind if your partner watched it? How about together vs alone?
14- What is an embarrassing moment in your life? How about your most embarrassing?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
19- What’s your favorite fairytale? What’s your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
34- Ever been to a concert? What was your favorite? Who would you like to see?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
89~ Do you like taking showers together?
(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…)
3- Should Pluto still be considered a planet? 4- How about smoking?
12- What’s your favorite food? What’s your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Would you do it again, and would you rather 2 females or 2 males?
Do you think this brought you closer together?
19~ Who/when was your first “heartbreak”?
92~ Everyone needs a “safe” word. What is yours?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What is your view on sex? Meaning, When/Where/ How often/
Do you have a favorite? Is it ok if your partner does?
15- What bad habit do you wish you could quit? Do you have any addictions?
8- What's your favorite flavor of ice cream? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
The Ice Breaker Questions
17- Have you ever done drugs? Which ones? How often?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What have you learned about yourself that you did not before this?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
21~ What was the best date you ever went on? What has been the worst?
48~ Do you have any siblings? Are you close to your family?
If yes, what?
49~ How many times have you been married? Why did they end?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
22- What is your favorite childhood memory? What is your least favorite?
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
61~ How willing would you be to try new sexual positions?