What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 01:52
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
10- List 5 of your top pet peeves.
Get this wrong and this could mean the end… :-) some funny, some not…
Nurse/Patient Celebrity/Fan
Why do men prefer low-maintanence women?
9~ How many times over your lifetime do you think you have had sex so far?
49~ How many times have you been married? Why did they end?
1~ How old were you when you had your first kiss? Who? Care to Share?
21- What's your favorite way to spend a weekend or time off?
18~ Who/when was your first “crush”?
82~ Do you have any fantasies involving Role-Playing?
1- What was your first impression of me? Has it changed?
19- What’s your favorite fairytale? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How do I build rapport with anybody?
83~ How do you feel about Porn?
41~ Are there moments in your past that you would want to change? Please share 3 of 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?
What might be the social consequences of an ethnic as opposed to a civic conception of the nation?
Do you like it when they show and tell you what they want?
6- Do you have dreams? Can you remember them? What do you usually dream about?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
11- How about if they like a certain sports team? 12-How about drinking too much?
Do you have a favorite? Is it ok if your partner does?
What would be the lowest score with 9 strikes and no gutter balls?
Would you ever want to be woken up with oral and/or intercourse?
3- What’s your favorite smell? Do you a least favorite?
18- How often do you drink alcohol? What is your favorite drink?
53~ How much can you tell me about the one thing you are most passionate about?
Do you like the “69” position? Do you prefer to be on top or bottom?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What are the best items to buy from a furniture shop?
If you say it, I will stop, and we can talk about it when you are ready.
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?
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 scene is considered the most difficult to watch in each of Quentin Tarantino's movies?
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?
37- Do you like your name? If you could change it, what would you change it too?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Why does Boko Haram attack its own Muslims?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Why am I always so tired, no matter how much I sleep?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
17- Have you ever done drugs? Which ones? How often?
11- What's your favorite restaurant? What’s your least favorite?
Trump must stop the AI bloodbath before it’s too late - The Hill
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
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,
Harvard doctor lists 6 cancer causing foods: What are their alternatives - Times of India
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?
13~ Is there a difference between, making love, having sex, and fucking?
Would you read them together?
If yes, what?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
36~ What is your favorite time of day to have sex/make love?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How many partners have you had oral sex with? Who? Care to Share?
28- What are some things that people do that irritate you?
4- For a pet, Cat, dog or other?
71~ Would you give your partner a hand or foot job? Would you receive one?
92~ Have you ever had or have an STD? How many? What was it?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
That one or two things that made you go hmmmm, OMG or wow!
28~ What are some things that turn on? What is your biggest turn on?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
5- Have you ever been hypnotized? Would you allow yourself to be?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
42~ What’s your biggest regret in life?
70~ Would/do you have/like anal sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Please share Did you stop?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
If NO, would you ever have one? Would it be with 2 men or 2 women?
If YES, was it with 2 men or 2 women? Did you enjoy it?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
20- What’s your favorite candy? What’s your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
23- What is your dream job? What was it as a child?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
52~ What are your hobbies?
36- Do you play video games? What is your favorite? Do you a least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
51~ What tends to bring a smile to your face?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
15~ Have you ever been “in love”? Who? Care to Share?
Escort/Client Job Applicant/Hiring Manager
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
48~ Have you ever paid or been paid for sex?
Do you watch it? What is your favorite?
2- What’s your favorite color? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
19- Do/have you smoked? What do you prefer? How often?
38~ Share your most embarrassing sexual memory?
92~ Everyone needs a “safe” word. What is yours?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
22- What is your favorite childhood memory? What is your least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
*** Deal Breaker Questions ***
12- What’s your favorite food? What’s your least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
11~ Have you ever been caught by your parents or children or others while having 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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
29~ What are some things that turn you off? What is your biggest turn off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
34- Ever been to a concert? What was your favorite? Who would you like to see?
33- If you could visit any time period, when would you pick? Please explain why?
51~ Are you willing to play adult games with your partner?
13- What is the craziest/scariest thing you've ever done?
*** Questions About Me ***
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…
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What would you say to prove to yourself that it was really you?
50~ How many children do you have? What are their ages?
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?
29- How superstitious are you?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
84~ How do you feel about reading/listening to adult stories?
44~ Care to share something about yourself that no one else knows about you?
9- If you could have three wishes, what would they be? Why?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Have you ever? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
76~ Have you had a threesome? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
30~ What's something unexpected that turns you on?
81~ Do you have any kinks and/or fetishes?
9- What’s your favorite season and why? What’s your least favorite?
*** What’s Your Favorite…? ***
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
* Give a rating for each one (0-100)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
17- What’s your favorite holiday? What’s your least favorite?
You know that I will be 100% truthful, so ask.
25~ How do you feel about PDA? (Public Display of Affection)
Doctor/Nurse Stripper/Client
49~ If you could, would you want to be the opposite sex for a day, week, or year?
10~ How many dates are necessary before you to have sex with someone?
14- What's your favorite dessert? Do you a least favorite?
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?
(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…)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Family Relation Age Play
67~ Do you like it when your partner moans and/or is vocal during sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
*** Random Questions ***
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
12- What is the weirdest thing you've ever eaten?
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?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Would /have you ever given your partner a lap dance and Striptease?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Does the thought excite you? Care to share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
62~ Have you used adult toys?
How old are you? Male or Female?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Master/Slave Boss/Maid
What have you learned about me that was new and/or surprising?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
21~ What was the best date you ever went on? What has been the worst?
32- What's your greatest talent? Can I see it right now?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How many times do you think you have “made love”?
39~ What are your love languages?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
45~ How do you feel about me blindfolding you? How about blindfolding me?
13- What’s your favorite drink? What’s your least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
What was the longest? What was the shortest?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
15- What bad habit do you wish you could quit? Do you have any addictions?
*** Questions about Relationships/Past ***
8- What's your favorite flavor of ice cream? Do you a least favorite?
5~ When you first started having sex, was it what you thought it would be?
26~ What side of the bed do you sleep on?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Any that are a turn off?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Can you Deep Throat? Do you like the taste of yourself?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Do you think this brought you closer together?
3- Should Pluto still be considered a planet? 4- How about smoking?
Nothing too Serious
Teacher/Student Stranger/One Night Stand
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Would you mind if your partner watched it? How about together vs alone?
34~ Do you like the lights on or off during sex?
Model/Photographer Police/Criminal
48~ Do you have any siblings? Are you close to your family?
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?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
3- What Superhero or Superpower would you want to be/have?
10- What is your favorite family tradition? What’s your least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
8- What are your thoughts on politics?
11- List at least 5 things on your bucket list. Have you done any of them already?
Any that are a turn off?
61~ How willing would you be to try new sexual positions?
If you win, what will you make them do?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
What is your favorite position? Why?
80~ Share your top three fantasies/desires. (Be detailed) 😊
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
The Ice Breaker Questions
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Will you cheat again? How can, you be sure? Define what cheating is to you.
19~ Who/when was your first “heartbreak”?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What is your view on sex? Meaning, When/Where/ How often/
33- Beach or Mountains? Or is there another place to like better?
7- What are your thoughts on religion? Is there an afterlife?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
27- What was/ is nickname? Does it have a meaning behind it?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
What have you learned about yourself that you did not before this?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
47~ What would be your dream job and why?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
13- How about having a certain hair cut/style?
How about if they talk dirty and/or call you names?
22- Do you have any birth marks? How about scars? Care to share how you got them?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
65~ Describe the best orgasm you’ve ever had? Care to share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Over time has your thoughts on sex changed?
7- What if a person smells a certain way? 8- How about smoking?
7-What do I do in bed that drives you wild? How about, what turns you off?
31- If given a chance to be immortal, would you take it? Why?
89~ Do you like taking showers together?
Repairman/Lonely Wife Virgin/Experienced
Would you allow me to clean every part of your body with my soapy hands and fingers?
How well do you know me? And some of your thoughts about me
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
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?
52~ Are you willing to make “those types” of bets with your partner?