What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 06:27
11- What's your favorite restaurant? What’s your least favorite?
30~ What's something unexpected that turns you on?
9- What’s your favorite season and why? What’s your least favorite?
Is Tinder the best dating app?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
I would allow you to do it… What would you do to me?
8- What are your thoughts on politics?
Can men enjoy receiving anal sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
28- What are some things that people do that irritate you?
What is the most peculiar thing about the human brain?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
29- How superstitious are you?
I've never read the book. What did Dorian Grey do that was so immoral and sinful?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
What are some cool confidence hacks?
How many times do you think you have “made love”?
Escort/Client Job Applicant/Hiring Manager
52~ What are your hobbies?
Does CloudFlare protect blackhat sites from DDOS attacks?
27- What was/ is nickname? Does it have a meaning behind it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Why don't I want to talk to my girlfriend when she loves me a lot? I feel bored.
42~ What’s your biggest regret in life?
19- What’s your favorite fairytale? What’s your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
What is your review of The Office (U.S. TV series)?
6- Do you have dreams? Can you remember them? What do you usually dream about?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
36~ What is your favorite time of day to have sex/make love?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
92~ Everyone needs a “safe” word. What is yours?
What are some ballbusting stories?
43~ Ever had your hair pulled 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?
7-What do I do in bed that drives you wild? How about, what turns you off?
18~ Who/when was your first “crush”?
If you win, what will you make them do?
10- What is your favorite family tradition? What’s your least favorite?
Will Canadians still buy American products?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Family Relation Age Play
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Why do many women like tall men?
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?
38~ Share your most embarrassing sexual memory?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Doctor/Nurse Stripper/Client
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
23- What is your dream job? What was it as a child?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Nurse/Patient Celebrity/Fan
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
12- What is the weirdest thing you've ever eaten?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Would you read them together?
33- If you could visit any time period, when would you pick? Please explain why?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
1- What’s your favorite animal? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
92~ Have you ever had or have an STD? How many? What was it?
67~ Do you like it when your partner moans and/or is vocal during sex?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
44~ Care to share something about yourself that no one else knows about you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
26~ What side of the bed do you sleep on?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
How well do you know me? And some of your thoughts about me
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
2- What’s your favorite color? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
*** Random Questions ***
1- What was your first impression of me? Has it changed?
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?
Prisoner/Prison Guard Landlord/Tenant
17- Have you ever done drugs? Which ones? How often?
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)
11- How about if they like a certain sports team? 12-How about drinking too much?
(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…)
What is your view on sex? Meaning, When/Where/ How often/
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
40~ What’s the weirdest place you’ve ever had sex?
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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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 if a person smells a certain way? 8- How about smoking?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
11~ Have you ever been caught by your parents or children or others while having sex?
60~ How important is oral sex? Do you like receiving? Do you like giving?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
11- List at least 5 things on your bucket list. Have you done any of them already?
61~ How willing would you be to try new sexual positions?
71~ Would you give your partner a hand or foot job? Would you receive one?
9~ How many times over your lifetime do you think you have had sex so far?
51~ Are you willing to play adult games with your partner?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
49~ How many times have you been married? Why did they end?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
7- What are your thoughts on religion? Is there an afterlife?
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
What is your favorite position? Why?
If you say it, I will stop, and we can talk about it when you are ready.
32- What's your greatest talent? Can I see it right now?
18- How often do you drink alcohol? What is your favorite drink?
9- Is there something you’ve always wanted to ask me but you’re afraid?
14- What's your favorite dessert? Do you a least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
15- What bad habit do you wish you could quit? Do you have any addictions?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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,
The Ice Breaker Questions
1~ How old were you when you had your first kiss? Who? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
*** Deal Breaker Questions ***
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
29~ What are some things that turn you off? What is your biggest turn off?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** What’s Your Favorite…? ***
Nothing too Serious
How old are you? Male or Female?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
17- What’s your favorite holiday? What’s your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
20- What’s your favorite candy? What’s your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
Please share Did you stop?
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?
62~ Have you used adult toys?
13- What is the craziest/scariest thing you've ever done?
80~ Share your top three fantasies/desires. (Be detailed) 😊
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
*** Questions about Relationships/Past ***
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
83~ How do you feel about Porn?
34- Ever been to a concert? What was your favorite? Who would you like to see?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
65~ Describe the best orgasm you’ve ever had? Care to share?
19- Do/have you smoked? What do you prefer? How often?
33- Beach or Mountains? Or is there another place to like better?
51~ What tends to bring a smile to your face?
89~ Do you like taking showers together?
What have you learned about yourself that you did not before this?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Do you have a favorite? Is it ok if your partner does?
* Give a rating for each one (0-100)
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?
What was the longest? What was the shortest?
50~ How many children do you have? What are their ages?
That one or two things that made you go hmmmm, OMG or wow!
19~ Who/when was your first “heartbreak”?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
(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?
Over time has your thoughts on sex changed?
Would you do it again, and would you rather 2 females or 2 males?
45~ How do you feel about me blindfolding you? How about blindfolding 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?
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…
13- How about having a certain hair cut/style?
10~ How many dates are necessary before you to have sex with someone?
82~ Do you have any fantasies involving Role-Playing?
Teacher/Student Stranger/One Night Stand
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Have you ever? Care to Share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
10- List 5 of your top pet peeves.
15- What's your favorite saying? What word or phrase is your least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Any that are a turn off?
28~ What are some things that turn on? What is your biggest turn on?
Get this wrong and this could mean the end… :-) some funny, some not…
You know that I will be 100% truthful, so ask.
What have you learned about me that was new and/or surprising?
Do you think this brought you closer together?
4- For a pet, Cat, dog or other?
Does the thought excite you? Care to share?
5- Have you ever been hypnotized? Would you allow yourself to be?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would you mind if your partner watched it? How about together vs alone?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
48~ Have you ever paid or been paid for sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Do you watch it? What is your favorite?
13~ Is there a difference between, making love, having sex, and fucking?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Model/Photographer Police/Criminal
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
*** Questions About Me ***
76~ Have you had a threesome? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
47~ What would be your dream job and why?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
How about if they talk dirty and/or call you names?
3- What’s your favorite smell? Do you a least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Would /have you ever given your partner a lap dance and Striptease?
39~ What are your love languages?
What is your favorite toy? Ever wanted to try a specific toy?
37- Do you like your name? If you could change it, what would you change it too?
Any that are a turn off?
12- What’s your favorite food? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Master/Slave Boss/Maid
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
What would you say to prove to yourself that it was really you?
3- Should Pluto still be considered a planet? 4- How about smoking?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
70~ Would/do you have/like anal sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
25~ How do you feel about PDA? (Public Display of Affection)
15~ Have you ever been “in love”? Who? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
If YES, was it with 2 men or 2 women? Did you enjoy it?
22- Do you have any birth marks? How about scars? Care to share how you got them?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
21- What's your favorite way to spend a weekend or time off?
How many partners have you had oral sex with? Who? 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?
48~ Do you have any siblings? Are you close to your family?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Repairman/Lonely Wife Virgin/Experienced
5~ When you first started having sex, was it what you thought it would be?
Do you like the “69” position? Do you prefer to be on top or bottom?
If yes, what?
52~ Are you willing to make “those types” of bets with your partner?
9- If you could have three wishes, what would they be? Why?
34~ Do you like the lights on or off during sex?
84~ How do you feel about reading/listening to adult stories?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
8- What's your favorite flavor of ice cream? Do you a least favorite?
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…
3- What Superhero or Superpower would you want to be/have?
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?