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