What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 03:35
What is your view on sex? Meaning, When/Where/ How often/
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
38~ Share your most embarrassing sexual memory?
What are the most significant instances of romantic jealousy in the Harry Potter series?
36~ What is your favorite time of day to have sex/make love?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
10- List 5 of your top pet peeves.
Feather-legged lace weaver spider kills prey by covering it with toxic silk - Phys.org
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
How many times do you think you have “made love”?
Prisoner/Prison Guard Landlord/Tenant
Bruce Willis’ Family Share Heartbreaking Health Update on ‘Die Hard’ Star - TV Insider
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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?
Why does my sister want to have sex with me? What should I do?
28- What are some things that people do that irritate you?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
47~ What would be your dream job and why?
What was the first Native American tribe to inhabit Long Island, NY?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Why do some people have sex with dogs?
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?
76~ Have you had a threesome? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What is your review of "Regent", episode 5 of Season 2 House of the Dragon?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
9~ How many times over your lifetime do you think you have had sex so far?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Why do people who were very kind and loving once become cold-hearted?
Would you allow me to clean every part of your body with my soapy hands and fingers?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What would you say to prove to yourself that it was really you?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
92~ Everyone needs a “safe” word. What is yours?
Teens like me, what are your expectations when entering adulthood?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
67~ Do you like it when your partner moans and/or is vocal during sex?
83~ How do you feel about Porn?
12- What is the weirdest thing you've ever eaten?
33- Beach or Mountains? Or is there another place to like better?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What have you learned about me that was new and/or surprising?
What are 5 ways that can be done by the community to improve the public transport system?
51~ What tends to bring a smile to your face?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
11- List at least 5 things on your bucket list. Have you done any of them already?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
11~ Have you ever been caught by your parents or children or others while having sex?
If you win, what will you make them do?
15- What bad habit do you wish you could quit? Do you have any addictions?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) 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.
Do you think this brought you closer together?
Will you cheat again? How can, you be sure? Define what cheating is to you.
21~ What was the best date you ever went on? What has been the worst?
*** Deal Breaker Questions ***
31- If given a chance to be immortal, would you take it? Why?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What was the longest? What was the shortest?
Master/Slave Boss/Maid
21- What's your favorite way to spend a weekend or time off?
If YES, was it with 2 men or 2 women? Did you enjoy it?
14- What's your favorite dessert? 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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Get this wrong and this could mean the end… :-) some funny, some not…
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
60~ How important is oral sex? Do you like receiving? Do you like giving?
1- What’s your favorite animal? Do you a least favorite?
Would /have you ever given your partner a lap dance and Striptease?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
5- Have you ever been hypnotized? Would you allow yourself to be?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
8- What's your favorite flavor of ice cream? 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?
84~ How do you feel about reading/listening to adult stories?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
11- What's your favorite restaurant? What’s your least favorite?
23- What is your dream job? What was it as a child?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How old are you? Male or Female?
15- What's your favorite saying? What word or phrase is your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
92~ Have you ever had or have an STD? How many? What was it?
* Give a rating for each one (0-100)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
7- What are your thoughts on religion? Is there an afterlife?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
39~ What are your love languages?
8- What are your thoughts on politics?
3- What Superhero or Superpower would you want to be/have?
82~ Do you have any fantasies involving Role-Playing?
5~ When you first started having sex, was it what you thought it would be?
30~ What's something unexpected that turns you on?
34~ Do you like the lights on or off during sex?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
25~ How do you feel about PDA? (Public Display of Affection)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
2- What’s your favorite color? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
65~ Describe the best orgasm you’ve ever had? Care to share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Escort/Client Job Applicant/Hiring Manager
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
17- What’s your favorite holiday? What’s your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
You know that I will be 100% truthful, so ask.
13~ Is there a difference between, making love, having sex, and fucking?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Over time has your thoughts on sex changed?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
What is your favorite toy? Ever wanted to try a specific toy?
22- What is your favorite childhood memory? What is your 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?
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Would you read them together?
*** Questions about Relationships/Past ***
13- What is the craziest/scariest thing you've ever done?
If you say it, I will stop, and we can talk about it when you are ready.
Any that are a turn off?
14- What is an embarrassing moment in your life? How about your most embarrassing?
33- If you could visit any time period, when would you pick? Please explain why?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
11- How about if they like a certain sports team? 12-How about drinking too much?
Teacher/Student Stranger/One Night Stand
10- What is your favorite family tradition? What’s your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
40~ What’s the weirdest place you’ve ever had sex?
Would you do it again, and would you rather 2 females or 2 males?
19~ Who/when was your first “heartbreak”?
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?
17- Have you ever done drugs? Which ones? How often?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Repairman/Lonely Wife Virgin/Experienced
If yes, what?
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?
1- What was your first impression of me? Has it changed?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
(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…)
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?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
20- What’s your favorite candy? What’s your least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
53~ How much can you tell me about the one thing you are most passionate about?
50~ How many children do you have? What are their ages?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Any that are a turn 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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Nothing too Serious
Would you mind if your partner watched it? How about together vs alone?
61~ How willing would you be to try new sexual positions?
3- What’s your favorite smell? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
62~ Have you used adult toys?
Please share Did you stop?
29~ What are some things that turn you off? What is your biggest turn off?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Does the thought excite you? Care to share?
How well do you know me? And some of your thoughts about me
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…
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
51~ Are you willing to play adult games with your partner?
Model/Photographer Police/Criminal
The Ice Breaker Questions
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,
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
*** Random Questions ***
48~ Have you ever paid or been paid for sex?
Doctor/Nurse Stripper/Client
36- Do you play video games? What is your favorite? Do you a least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
28~ What are some things that turn on? What is your biggest turn on?
12- What’s your favorite food? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
52~ What are your hobbies?
Do you have a favorite? Is it ok if your partner does?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
42~ What’s your biggest regret in life?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
9- Is there something you’ve always wanted to ask me but you’re afraid?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Have you ever? 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?
19- What’s your favorite fairytale? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
4- For a pet, Cat, dog or other?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
That one or two things that made you go hmmmm, OMG or wow!
26~ What side of the bed do you sleep on?
48~ Do you have any siblings? Are you close to your family?
13- How about having a certain hair cut/style?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
9- What’s your favorite season and why? What’s your least favorite?
Do you like it when they show and tell you what they want?
34- Ever been to a concert? What was your favorite? Who would you like to see?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
I would allow you to do it… What would you do to me?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
What is your favorite position? Why?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
9- If you could have three wishes, what would they be? Why?
89~ Do you like taking showers together?
13- What’s your favorite drink? What’s your least favorite?
*** Questions About Me ***
32- What's your greatest talent? Can I see it right now?
44~ Care to share something about yourself that no one else knows about you?
Nurse/Patient Celebrity/Fan
15~ Have you ever been “in love”? Who? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
70~ Would/do you have/like anal sex?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Family Relation Age Play
What have you learned about yourself that you did not before this?
37- Do you like your name? If you could change it, what would you change it too?
10~ How many dates are necessary before you to have sex with someone?
49~ How many times have you been married? Why did they end?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
18~ Who/when was your first “crush”?
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…
81~ Do you have any kinks and/or fetishes?
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)
7- What if a person smells a certain way? 8- How about smoking?
18- How often do you drink alcohol? What is your favorite drink?
3- Should Pluto still be considered a planet? 4- How about smoking?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Would you ever want to be woken up with oral and/or intercourse?
How about if they talk dirty and/or call you names?
Do you watch it? What is your favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
How many partners have you had oral sex with? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
71~ Would you give your partner a hand or foot job? Would you receive one?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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?
29- How superstitious are you?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
52~ Are you willing to make “those types” of bets with your partner?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
*** What’s Your Favorite…? ***
45~ How do you feel about me blindfolding you? How about blindfolding me?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?