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