What is the most interesting question you can ask to get to know someone?
Last Updated: 24.06.2025 03:50
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
11- How about if they like a certain sports team? 12-How about drinking too much?
3- What Superhero or Superpower would you want to be/have?
What’s the saddest thing you’ve seen at your job?
Teacher/Student Stranger/One Night Stand
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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18- How often do you drink alcohol? What is your favorite drink?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
You know that I will be 100% truthful, so ask.
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12- What’s your favorite food? What’s your least favorite?
9- If you could have three wishes, what would they be? Why?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Have you ever really seen aliens or UFOs by yourself? Can you share your experience?
Do you have a favorite? Is it ok if your partner does?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Have you ever? Care to Share?
Do foreign workers face discrimination in Canada?
12- What is the weirdest thing you've ever eaten?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
82~ Do you have any fantasies involving Role-Playing?
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How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
25~ How do you feel about PDA? (Public Display of Affection)
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24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would you do it again, and would you rather 2 females or 2 males?
If you win, what will you make them do?
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29~ What are some things that turn you off? What is your biggest turn off?
Get this wrong and this could mean the end… :-) some funny, some not…
67~ Do you like it when your partner moans and/or is vocal during sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
62~ Have you used adult toys?
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5~ When you first started having sex, was it what you thought it would be?
If yes, what?
29- How superstitious are you?
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52~ Are you willing to make “those types” of bets with your partner?
Any that are a turn off?
11- What's your favorite restaurant? What’s your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
36~ What is your favorite time of day to have sex/make love?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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*** Random Questions ***
*** Questions about Relationships/Past ***
10~ How many dates are necessary before you to have sex with someone?
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80~ Share your top three fantasies/desires. (Be detailed) 😊
18~ Who/when was your first “crush”?
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What is your view on sex? Meaning, When/Where/ How often/
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
10- What is your favorite family tradition? What’s your 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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
11~ Have you ever been caught by your parents or children or others while having sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
13~ Is there a difference between, making love, having sex, and fucking?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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…
What do you dislike about me? I asked you to be 100% honest.
83~ How do you feel about Porn?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Nothing too Serious
84~ How do you feel about reading/listening to adult stories?
48~ Do you have any siblings? Are you close to your family?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Prisoner/Prison Guard Landlord/Tenant
28~ What are some things that turn on? What is your biggest turn on?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
What is your favorite position? Why?
Does the thought excite you? Care to share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Master/Slave Boss/Maid
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)
27- What was/ is nickname? Does it have a meaning behind it?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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,
70~ Would/do you have/like anal sex?
Would you ever want to be woken up with oral and/or intercourse?
Do you like it when they show and tell you what they want?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
How many times do you think you have “made love”?
What was the longest? What was the shortest?
9~ How many times over your lifetime do you think you have had sex so far?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
That one or two things that made you go hmmmm, OMG or wow!
Nurse/Patient Celebrity/Fan
92~ Have you ever had or have an STD? How many? What was it?
Do you think this brought you closer together?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
What is your favorite toy? Ever wanted to try a specific toy?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
76~ Have you had a threesome? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
* Give a rating for each one (0-100)
33- If you could visit any time period, when would you pick? Please explain why?
What have you learned about yourself that you did not before this?
42~ What’s your biggest regret in life?
Can you Deep Throat? Do you like the taste of yourself?
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 prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
48~ Have you ever paid or been paid for sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
2- What’s your favorite color? Do you a least favorite?
51~ What tends to bring a smile to your face?
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?
Would you read them together?
20- What’s your favorite candy? What’s your least favorite?
33- Beach or Mountains? Or is there another place to like better?
38~ Share your most embarrassing sexual memory?
How well do you know me? And some of your thoughts about me
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Model/Photographer Police/Criminal
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
11- List at least 5 things on your bucket list. Have you done any of them already?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
21~ What was the best date you ever went on? What has been the worst?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
15~ Have you ever been “in love”? Who? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
8- What are your thoughts on politics?
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?
50~ How many children do you have? What are their ages?
19- What’s your favorite fairytale? What’s your least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
28- What are some things that people do that irritate you?
44~ Care to share something about yourself that no one else knows about you?
36- Do you play video games? What is your favorite? Do you a least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
32- What's your greatest talent? Can I see it right now?
53~ How much can you tell me about the one thing you are most passionate about?
19~ Who/when was your first “heartbreak”?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
31- If given a chance to be immortal, would you take it? Why?
Family Relation Age Play
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Any that are a turn off?
22- Do you have any birth marks? How about scars? Care to share how you got them?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
37- Do you like your name? If you could change it, what would you change it too?
(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…)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Doctor/Nurse Stripper/Client
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
7- What are your thoughts on religion? Is there an afterlife?
15- What's your favorite saying? What word or phrase is your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
52~ What are your hobbies?
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?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
How about if they talk dirty and/or call you names?
21- What's your favorite way to spend a weekend or time off?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What have you learned about me that was new and/or surprising?
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?
1~ How old were you when you had your first kiss? Who? Care to Share?
61~ How willing would you be to try new sexual positions?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
*** What’s Your Favorite…? ***
14- What's your favorite dessert? Do you a least favorite?
What would you say to prove to yourself that it was really you?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you watch it? What is your favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
51~ Are you willing to play adult games with your partner?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
30~ What's something unexpected that turns you on?
Repairman/Lonely Wife Virgin/Experienced
13- What’s your favorite drink? What’s your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
The Ice Breaker Questions
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
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…
22~ What is the best pickup line anyone has ever used on you? What was the worst?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
49~ How many times have you been married? Why did they end?
If you say it, I will stop, and we can talk about it when you are ready.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
13- What is the craziest/scariest thing you've ever done?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
9- What’s your favorite season and why? 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.
If YES, was it with 2 men or 2 women? Did you enjoy it?
4- For a pet, Cat, dog or other?
15- What bad habit do you wish you could quit? Do you have any addictions?
Please share Did you stop?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
1- What’s your favorite animal? Do you a least favorite?
17- What’s your favorite holiday? What’s your least favorite?
34~ Do you like the lights on or off during sex?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
If NO, would you ever have one? Would it be with 2 men or 2 women?
39~ What are your love languages?
26~ What side of the bed do you sleep on?
How old are you? Male or Female?
Escort/Client Job Applicant/Hiring Manager
22- What is your favorite childhood memory? What is your least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
10- List 5 of your top pet peeves.
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
19- Do/have you smoked? What do you prefer? How often?
Will you cheat again? How can, you be sure? Define what cheating is to you.
17- Have you ever done drugs? Which ones? How often?
How many partners have you had oral sex with? Who? Care to Share?
5- Have you ever been hypnotized? Would you allow yourself to be?
13- How about having a certain hair cut/style?
Over time has your thoughts on sex changed?
89~ Do you like taking showers together?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
*** Questions About Me ***
47~ What would be your dream job and why?
*** Deal Breaker Questions ***
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
40~ What’s the weirdest place you’ve ever had sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
23- What is your dream job? What was it as a child?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
1- What was your first impression of me? Has it changed?
Would you mind if your partner watched it? How about together vs alone?
3- Should Pluto still be considered a planet? 4- How about smoking?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Would /have you ever given your partner a lap dance and Striptease?
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)
I would allow you to do it… What would you do to me?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
7-What do I do in bed that drives you wild? How about, what turns you off?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
7- What if a person smells a certain way? 8- How about smoking?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?