What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 02:27
26~ What side of the bed do you sleep on?
How many partners have you had oral sex with? Who? Care to Share?
48~ Have you ever paid or been paid for sex?
Why don't men find fat women attractive?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
61~ How willing would you be to try new sexual positions?
3- Should Pluto still be considered a planet? 4- How about smoking?
*** Questions about Relationships/Past ***
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
*** What’s Your Favorite…? ***
50~ How many children do you have? What are their ages?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Why do men say women hit the wall at 24?
The Ice Breaker Questions
Doctor/Nurse Stripper/Client
29~ What are some things that turn you off? What is your biggest turn off?
Do you watch it? What is your favorite?
How old are you? Male or Female?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
The odd effects a year in space has on the bodies of astronauts - supercarblondie.com
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
If you say it, I will stop, and we can talk about it when you are ready.
2- What’s your favorite color? Do you a least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
52~ Are you willing to make “those types” of bets with your partner?
She Spotted a Detail in a Photo and Knew Immediately—Her Marriage Was Over - Jason Deegan
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
64~ When was your very first orgasm? When was your first from having sex? Care to share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
8- What are your thoughts on politics?
What is the dirtiest city in India?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
11~ Have you ever been caught by your parents or children or others while having sex?
33- Beach or Mountains? Or is there another place to like better?
If you could go back and rewrite the Legend of Korra, what would you change, and why?
Any that are a turn off?
49~ How many times have you been married? Why did they end?
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…
Why do many Hong Kong Chinese look different from the Han Chinese in mainland China?
51~ What tends to bring a smile to your face?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
If yes, what?
How do flat Earthers explain the existence of other spherical planets?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
92~ Everyone needs a “safe” word. What is yours?
What would you say to prove to yourself that it was really you?
What is the best way to get over your ex?
How well do you know me? And some of your thoughts about me
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)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
45~ How do you feel about me blindfolding you? How about blindfolding me?
38~ Share your most embarrassing sexual memory?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Have you ever? Care to Share?
13- What is the craziest/scariest thing you've ever done?
48~ Do you have any siblings? Are you close to your family?
11- How about if they like a certain sports team? 12-How about drinking too much?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
12- What is the weirdest thing you've ever eaten?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What is your view on sex? Meaning, When/Where/ How often/
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Any that are a turn off?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
27- What was/ is nickname? Does it have a meaning behind it?
15~ Have you ever been “in love”? Who? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you allow me to clean every part of your body with my soapy hands and fingers?
19- What’s your favorite fairytale? 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.
1- What was your first impression of me? Has it changed?
5- Have you ever been hypnotized? Would you allow yourself to be?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
7-What do I do in bed that drives you wild? How about, what turns you off?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Would you mind if your partner watched it? How about together vs alone?
67~ Do you like it when your partner moans and/or is vocal during sex?
I would allow you to do it… What would you do to me?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
80~ Share your top three fantasies/desires. (Be detailed) 😊
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
10- What is your favorite family tradition? What’s your least favorite?
14- What's your favorite dessert? Do you a least favorite?
89~ Do you like taking showers together?
51~ Are you willing to play adult games with your partner?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
What do you dislike about me? I asked you to be 100% honest.
13- How about having a certain hair cut/style?
17- Have you ever done drugs? Which ones? How often?
10~ How many dates are necessary before you to have sex with someone?
What have you learned about yourself that you did not before this?
28~ What are some things that turn on? What is your biggest turn on?
Nothing too Serious
17- What’s your favorite holiday? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Please share Did you stop?
Would you ever want to be woken up with oral and/or intercourse?
Teacher/Student Stranger/One Night Stand
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Would you do it again, and would you rather 2 females or 2 males?
Do you think this brought you closer together?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
15- What's your favorite saying? What word or phrase is your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
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?
47~ What would be your dream job and why?
(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…)
8- What's your favorite flavor of ice cream? Do you a least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
92~ Have you ever had or have an STD? How many? What was it?
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?
71~ Would you give your partner a hand or foot job? Would you receive one?
52~ What are your hobbies?
You know that I will be 100% truthful, so ask.
Does the thought excite you? Care to share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
31- If given a chance to be immortal, would you take it? Why?
How about if they talk dirty and/or call you names?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
65~ Describe the best orgasm you’ve ever had? Care to share?
What was the longest? What was the shortest?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Repairman/Lonely Wife Virgin/Experienced
Do you have a favorite? Is it ok if your partner does?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
19- Do/have you smoked? What do you prefer? How often?
What is your favorite toy? Ever wanted to try a specific toy?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Can you Deep Throat? Do you like the taste of yourself?
40~ What’s the weirdest place you’ve ever had sex?
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?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
21~ What was the best date you ever went on? What has been the worst?
10- List 5 of your top pet peeves.
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
37- Do you like your name? If you could change it, what would you change it too?
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?
42~ What’s your biggest regret in life?
84~ How do you feel about reading/listening to adult stories?
Prisoner/Prison Guard Landlord/Tenant
7- What if a person smells a certain way? 8- How about smoking?
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?
13- What’s your favorite drink? What’s your least favorite?
Would /have you ever given your partner a lap dance and Striptease?
7- What are your thoughts on religion? Is there an afterlife?
60~ How important is oral sex? Do you like receiving? Do you like giving?
18- How often do you drink alcohol? What is your favorite drink?
1~ How old were you when you had your first kiss? Who? Care to Share?
83~ How do you feel about Porn?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
11- List at least 5 things on your bucket list. Have you done any of them already?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
29- How superstitious are you?
Escort/Client Job Applicant/Hiring Manager
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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…
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
3- What Superhero or Superpower would you want to be/have?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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?
5~ When you first started having sex, was it what you thought it would be?
13~ Is there a difference between, making love, having sex, and fucking?
14- What is an embarrassing moment in your life? How about your most embarrassing?
21- What's your favorite way to spend a weekend or time off?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
*** Random Questions ***
81~ Do you have any kinks and/or fetishes?
53~ How much can you tell me about the one thing you are most passionate about?
Family Relation Age Play
4- For a pet, Cat, dog or other?
Master/Slave Boss/Maid
9~ How many times over your lifetime do you think you have had sex so far?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
82~ Do you have any fantasies involving Role-Playing?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
* Give a rating for each one (0-100)
30~ What's something unexpected that turns you on?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
32- What's your greatest talent? Can I see it right now?
33- If you could visit any time period, when would you pick? Please explain why?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
28- What are some things that people do that irritate you?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
34~ Do you like the lights on or off during sex?
*** Deal Breaker Questions ***
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
How many times do you think you have “made love”?
Do you like the “69” position? Do you prefer to be on top or bottom?
44~ Care to share something about yourself that no one else knows about you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
19~ Who/when was your first “heartbreak”?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Model/Photographer Police/Criminal
Would you read them together?
9- What’s your favorite season and why? What’s your least favorite?
18~ Who/when was your first “crush”?
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,
70~ Would/do you have/like anal sex?
That one or two things that made you go hmmmm, OMG or wow!
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
What have you learned about me that was new and/or surprising?
76~ Have you had a threesome? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
Nurse/Patient Celebrity/Fan
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
15- What bad habit do you wish you could quit? Do you have any addictions?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
*** Questions About Me ***
22- What is your favorite childhood memory? What is your least favorite?
What is your favorite position? Why?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
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?
20- What’s your favorite candy? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
62~ Have you used adult toys?
6- Do you have dreams? Can you remember them? What do you usually dream about?
1- What’s your favorite animal? Do you a least favorite?
12- What’s your favorite food? What’s your least favorite?
If you win, what will you make them do?
39~ What are your love languages?
Do you like it when they show and tell you what they want?
23- What is your dream job? What was it as a child?
9- If you could have three wishes, what would they be? Why?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
3- What’s your favorite smell? Do you a least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?