What is the most interesting question you can ask to get to know someone?
11.06.2025 03:18
3- Should Pluto still be considered a planet? 4- How about smoking?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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?
42~ What’s your biggest regret in life?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
19- Do/have you smoked? What do you prefer? How often?
83~ How do you feel about Porn?
Why is my Whirlpool fridge not cooling but the freezer works? What is the solution?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Would /have you ever given your partner a lap dance and Striptease?
Why do I feel so lazy every time I get into my room?
7- What are your thoughts on religion? Is there an afterlife?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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9- If you could have three wishes, what would they be? Why?
28~ What are some things that turn on? What is your biggest turn on?
Do you think this brought you closer together?
What do dreams about dead people mean?
80~ Share your top three fantasies/desires. (Be detailed) 😊
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
50~ How many children do you have? What are their ages?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Do you like it when they show and tell you what they want?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
9- Is there something you’ve always wanted to ask me but you’re afraid?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
What's the most sordid activity you've ever seen or heard about at a bachelorette party?
*** Deal Breaker Questions ***
*** Questions about Relationships/Past ***
92~ Have you ever had or have an STD? How many? What was it?
Why do some straight men enjoy wearing women's lingerie?
(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…)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Why do people with trauma easily recognize other people with trauma through eye contact?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Repairman/Lonely Wife Virgin/Experienced
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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Would you read them together?
That one or two things that made you go hmmmm, OMG or wow!
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
When you visit a store, do you go to shop or buy?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Please share Did you stop?
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?
Why is my ex trying to provoke an argument with me?
6- Do you have dreams? Can you remember them? What do you usually dream about?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
20- What’s your favorite candy? What’s your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
40~ What’s the weirdest place you’ve ever had sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
10- List 5 of your top pet peeves.
81~ Do you have any kinks and/or fetishes?
70~ Would/do you have/like anal sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What is your view on sex? Meaning, When/Where/ How often/
21~ What was the best date you ever went on? What has been the worst?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
36~ What is your favorite time of day to have sex/make love?
How old are you? Male or Female?
17- What’s your favorite holiday? What’s your least favorite?
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.
29- How superstitious are you?
2- What’s your favorite color? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
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30- Do you prefer living in the countryside, in a town, or in a big city? Why?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
15~ Have you ever been “in love”? Who? Care to Share?
*** Questions About Me ***
89~ Do you like taking showers together?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
5- Have you ever been hypnotized? Would you allow yourself to be?
18~ Who/when was your first “crush”?
The Ice Breaker Questions
Nurse/Patient Celebrity/Fan
11- How about if they like a certain sports team? 12-How about drinking too much?
17- Have you ever done drugs? Which ones? How often?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
If yes, what?
1- What’s your favorite animal? Do you a least favorite?
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?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What’s the longest time you gone without having sex, after, having it? How much time between the others?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
15- What bad habit do you wish you could quit? Do you have any addictions?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
23- What is your dream job? What was it as a child?
44~ Care to share something about yourself that no one else knows about you?
61~ How willing would you be to try new sexual positions?
Prisoner/Prison Guard Landlord/Tenant
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
9- What’s your favorite season and why? What’s your least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Does the thought excite you? Care to share?
Would you ever want to be woken up with oral and/or intercourse?
47~ What would be your dream job and why?
Nothing too Serious
Teacher/Student Stranger/One Night Stand
I would allow you to do it… What would you do to me?
Escort/Client Job Applicant/Hiring Manager
62~ Have you used adult toys?
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?
What is your favorite toy? Ever wanted to try a specific toy?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
*** What’s Your Favorite…? ***
1- What was your first impression of me? Has it changed?
Get this wrong and this could mean the end… :-) some funny, some not…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
22~ What is the best pickup line anyone has ever used on you? What was the worst?
51~ What tends to bring a smile to your face?
What would you say to prove to yourself that it was really you?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
25~ How do you feel about PDA? (Public Display of Affection)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
53~ How much can you tell me about the one thing you are most passionate about?
92~ Everyone needs a “safe” word. What is yours?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
52~ What are your hobbies?
48~ Do you have any siblings? Are you close to your family?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
11- What's your favorite restaurant? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
13- What’s your favorite drink? What’s your least favorite?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
65~ Describe the best orgasm you’ve ever had? Care to share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
12- What is the weirdest thing you've ever eaten?
76~ Have you had a threesome? Care to Share?
21- What's your favorite way to spend a weekend or time off?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
What have you learned about me that was new and/or surprising?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Do you watch it? What is your favorite?
37- Do you like your name? If you could change it, what would you change it too?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
82~ Do you have any fantasies involving Role-Playing?
Master/Slave Boss/Maid
84~ How do you feel about reading/listening to adult stories?
39~ What are your love languages?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
3- What’s your favorite smell? Do you a least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
67~ Do you like it when your partner moans and/or is vocal during sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
12- What’s your favorite food? What’s your least favorite?
10~ How many dates are necessary before you to have sex with someone?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
How many partners have you had oral sex with? Who? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
How well do you know me? And some of your thoughts about me
3- What Superhero or Superpower would you want to be/have?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
5~ When you first started having sex, was it what you thought it would be?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
49~ How many times have you been married? Why did they end?
34- Ever been to a concert? What was your favorite? Who would you like to see?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
22- What is your favorite childhood memory? What is your least favorite?
64~ When was your very first orgasm? When was your first from having sex? 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.
19- What’s your favorite fairytale? What’s your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Any that are a turn off?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
28- What are some things that people do that irritate you?
19~ Who/when was your first “heartbreak”?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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…
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?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Model/Photographer Police/Criminal
34~ Do you like the lights on or off during sex?
4- For a pet, Cat, dog or other?
11- List at least 5 things on your bucket list. Have you done any of them already?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Do you like the “69” position? Do you prefer to be on top or bottom?
You know that I will be 100% truthful, so ask.
7- What if a person smells a certain way? 8- How about smoking?
33- Beach or Mountains? Or is there another place to like better?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
26~ What side of the bed do you sleep on?
Would you allow me to clean every part of your body with my soapy hands and fingers?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Family Relation Age Play
48~ Have you ever paid or been paid for sex?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
1~ How old were you when you had your first kiss? Who? Care to Share?
Any that are a turn off?
7-What do I do in bed that drives you wild? How about, what turns you off?
* Give a rating for each one (0-100)
If you say it, I will stop, and we can talk about it when you are ready.
52~ Are you willing to make “those types” of bets with your partner?
What is your favorite position? Why?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
13~ Is there a difference between, making love, having sex, and fucking?
15- What's your favorite saying? What word or phrase is your least favorite?
What was the longest? What was the shortest?
32- What's your greatest talent? Can I see it right now?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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…
71~ Would you give your partner a hand or foot job? Would you receive one?
31- If given a chance to be immortal, would you take it? Why?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
*** Random Questions ***
8- What's your favorite flavor of ice cream? Do you a least favorite?
13- How about having a certain hair cut/style?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Can you Deep Throat? Do you like the taste of yourself?
33- If you could visit any time period, when would you pick? Please explain why?
11~ Have you ever been caught by your parents or children or others while having sex?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
51~ Are you willing to play adult games with your partner?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Would you mind if your partner watched it? How about together vs alone?
14- What's your favorite dessert? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
8- What are your thoughts on politics?
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)
10- What is your favorite family tradition? What’s your least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Over time has your thoughts on sex changed?
How many times do you think you have “made love”?
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?
Have you ever? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
14- What is an embarrassing moment in your life? How about your most embarrassing?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
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,
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What have you learned about yourself that you did not before this?
30~ What's something unexpected that turns you on?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
13- What is the craziest/scariest thing you've ever done?
27- What was/ is nickname? Does it have a meaning behind it?
If you win, what will you make them do?
18- How often do you drink alcohol? What is your favorite drink?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How about if they talk dirty and/or call you names?
Doctor/Nurse Stripper/Client