What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 00:09
70~ Would/do you have/like anal sex?
What do you dislike about me? I asked you to be 100% honest.
* Give a rating for each one (0-100)
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21- What's your favorite way to spend a weekend or time off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What is the best true Hollywood story you know?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
33- If you could visit any time period, when would you pick? Please explain why?
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56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
How well do you know me? And some of your thoughts about me
1- What’s your favorite animal? Do you a least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
10- What is your favorite family tradition? What’s your least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
7- What if a person smells a certain way? 8- How about smoking?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Any that are a turn off?
Would you mind if your partner watched it? How about together vs alone?
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42~ What’s your biggest regret in life?
89~ Do you like taking showers together?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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19- Do/have you smoked? What do you prefer? How often?
Nurse/Patient Celebrity/Fan
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Harvard gastroenterologist shares 4 bloat-busting tricks that actually work - Times of India
What would you say to prove to yourself that it was really you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
What is the best way to get revenge on people who hurt you?
26~ What side of the bed do you sleep on?
29~ What are some things that turn you off? What is your biggest turn off?
11- How about if they like a certain sports team? 12-How about drinking too much?
What are some fun/kinky things to do with your partner?
*** Deal Breaker Questions ***
3- What’s your favorite smell? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
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82~ Do you have any fantasies involving Role-Playing?
11~ Have you ever been caught by your parents or children or others while having sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Get this wrong and this could mean the end… :-) some funny, some not…
25~ How do you feel about PDA? (Public Display of Affection)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
6- Do you have dreams? Can you remember them? What do you usually dream about?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
11- List at least 5 things on your bucket list. Have you done any of them already?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How old are you? Male or Female?
15- What bad habit do you wish you could quit? Do you have any addictions?
39~ What are your love languages?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
36~ What is your favorite time of day to have sex/make love?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
13- What’s your favorite drink? What’s your 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,
If yes, what?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Model/Photographer Police/Criminal
Do you like it when they show and tell you what they want?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
What have you learned about yourself that you did not before this?
Would you ever want to be woken up with oral and/or intercourse?
32- What's your greatest talent? Can I see it right now?
14- What is an embarrassing moment in your life? How about your most embarrassing?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
How many times do you think you have “made love”?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
*** Questions About Me ***
22- What is your favorite childhood memory? What is your least favorite?
12- What is the weirdest thing you've ever eaten?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
If NO, would you ever have one? Would it be with 2 men or 2 women?
62~ Have you used adult toys?
46~ Have you ever used furniture, or other types of things to aid you 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?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
52~ What are your hobbies?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
22- Do you have any birth marks? How about scars? Care to share how you got them?
61~ How willing would you be to try new sexual positions?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Do you like the “69” position? Do you prefer to be on top or bottom?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
71~ Would you give your partner a hand or foot job? Would you receive one?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
19- What’s your favorite fairytale? What’s your least favorite?
48~ Do you have any siblings? Are you close to your family?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
21~ What was the best date you ever went on? What has been the worst?
Can you Deep Throat? Do you like the taste of yourself?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Do you think this brought you closer together?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
23- What is your dream job? What was it as a child?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
27- What was/ is nickname? Does it have a meaning behind it?
83~ How do you feel about Porn?
12- What’s your favorite food? What’s your least favorite?
Nothing too Serious
Doctor/Nurse Stripper/Client
92~ Everyone needs a “safe” word. What is yours?
Teacher/Student Stranger/One Night Stand
81~ Do you have any kinks and/or fetishes?
47~ What would be your dream job and why?
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?
50~ How many children do you have? What are their ages?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
10- List 5 of your top pet peeves.
17- What’s your favorite holiday? What’s your least favorite?
28- What are some things that people do that irritate you?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
52~ Are you willing to make “those types” of bets with your partner?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
15~ Have you ever been “in love”? Who? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
Would /have you ever given your partner a lap dance and Striptease?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you watch it? What is your favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Escort/Client Job Applicant/Hiring Manager
Prisoner/Prison Guard Landlord/Tenant
Master/Slave Boss/Maid
10~ How many dates are necessary before you to have sex with someone?
How about if they talk dirty and/or call you names?
31- If given a chance to be immortal, would you take it? Why?
*** Random Questions ***
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
13~ Is there a difference between, making love, having sex, and fucking?
Any that are a turn off?
53~ How much can you tell me about the one thing you are most passionate about?
29- How superstitious are you?
5- Have you ever been hypnotized? Would you allow yourself to be?
If you say it, I will stop, and we can talk about it when you are ready.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Would you do it again, and would you rather 2 females or 2 males?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
3- Should Pluto still be considered a planet? 4- How about smoking?
Please share Did you stop?
51~ Are you willing to play adult games with your partner?
76~ Have you had a threesome? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
34- Ever been to a concert? What was your favorite? Who would you like to see?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
9- If you could have three wishes, what would they be? Why?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
9- Is there something you’ve always wanted to ask me but you’re afraid?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
(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…)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
51~ What tends to bring a smile to your face?
*** Questions about Relationships/Past ***
What was the longest? What was the shortest?
5~ When you first started having sex, was it what you thought it would be?
17- Have you ever done drugs? Which ones? How often?
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?
3- What Superhero or Superpower would you want to be/have?
7-What do I do in bed that drives you wild? How about, what turns you off?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Family Relation Age Play
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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
If YES, was it with 2 men or 2 women? Did you enjoy it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
36- Do you play video games? What is your favorite? Do you a least favorite?
20- What’s your favorite candy? What’s your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Would you read them together?
What is your favorite position? Why?
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…
34~ Do you like the lights on or off during 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?
I would allow you to do it… What would you do to me?
40~ What’s the weirdest place you’ve ever had sex?
38~ Share your most embarrassing sexual memory?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
1~ How old were you when you had your first kiss? Who? Care to Share?
49~ How many times have you been married? Why did they end?
48~ Have you ever paid or been paid for sex?
That one or two things that made you go hmmmm, OMG or wow!
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?
14- What's your favorite dessert? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
65~ Describe the best orgasm you’ve ever had? Care to share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
15- What's your favorite saying? What word or phrase is your least favorite?
13- How about having a certain hair cut/style?
9~ How many times over your lifetime do you think you have had sex so far?
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…
19~ Who/when was your first “heartbreak”?
9- What’s your favorite season and why? What’s your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
30~ What's something unexpected that turns you on?
Do you have a favorite? Is it ok if your partner does?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
The Ice Breaker Questions
13- What is the craziest/scariest thing you've ever done?
37- Do you like your name? If you could change it, what would you change it too?
2- What’s your favorite color? Do you a least favorite?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
1- What was your first impression of me? Has it changed?
What have you learned about me that was new and/or surprising?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Over time has your thoughts on sex changed?
Repairman/Lonely Wife Virgin/Experienced
How many partners have you had oral sex with? Who? Care to Share?
84~ How do you feel about reading/listening to adult stories?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
8- What are your thoughts on politics?
7- What are your thoughts on religion? Is there an afterlife?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
18~ Who/when was your first “crush”?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
44~ Care to share something about yourself that no one else knows about you?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
4- For a pet, Cat, dog or other?
Does the thought excite you? Care to share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Would you allow me to clean every part of your body with my soapy hands and fingers?
What is your favorite toy? Ever wanted to try a specific toy?
You know that I will be 100% truthful, so ask.
Have you ever? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
8- What's your favorite flavor of ice cream? Do you a least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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?
What is your view on sex? Meaning, When/Where/ How often/
*** What’s Your Favorite…? ***
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
64~ When was your very first orgasm? When was your first from having sex? Care to share?