What is the most interesting question you can ask to get to know someone?
08.06.2025 02:09
29~ What are some things that turn you off? What is your biggest turn off?
I would allow you to do it… What would you do to me?
47~ What would be your dream job and why?
Why would a person always be so tired?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What are some ways to improve speed in sprinting, running uphill, and long/middle distance running?
52~ Are you willing to make “those types” of bets with your partner?
28~ What are some things that turn on? What is your biggest turn on?
70~ Would/do you have/like anal sex?
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6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
5~ When you first started having sex, was it what you thought it would be?
*** Questions about Relationships/Past ***
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12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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That one or two things that made you go hmmmm, OMG or wow!
23- What is your dream job? What was it as a child?
53~ How much can you tell me about the one thing you are most passionate about?
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71~ Would you give your partner a hand or foot job? Would you receive one?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
The One Food Registered Dietitians Say Isn’t as Healthy as Most People Think - Yahoo
84~ How do you feel about reading/listening to adult stories?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
Are there any real-life examples of prisoners who escaped from hospitals and were never caught?
*** Questions About Me ***
How well do you know me? And some of your thoughts about me
Do you watch it? What is your favorite?
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7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
29- How superstitious are you?
28- What are some things that people do that irritate you?
Would you ever want to be woken up with oral and/or intercourse?
34- Ever been to a concert? What was your favorite? Who would you like to see?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
20- What’s your favorite candy? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
7- What are your thoughts on religion? Is there an afterlife?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
*** What’s Your Favorite…? ***
What is your view on sex? Meaning, When/Where/ How often/
What would you say to prove to yourself that it was really you?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Model/Photographer Police/Criminal
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
*** Deal Breaker Questions ***
48~ Have you ever paid or been paid for sex?
What have you learned about me that was new and/or surprising?
You know that I will be 100% truthful, so ask.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
32- What's your greatest talent? Can I see it right now?
Any that are a turn off?
Will you cheat again? How can, you be sure? Define what cheating is to you.
26~ What side of the bed do you sleep on?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
7-What do I do in bed that drives you wild? How about, what turns you off?
Can you Deep Throat? Do you like the taste of yourself?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
13- How about having a certain hair cut/style?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Would you mind if your partner watched it? How about together vs alone?
Over time has your thoughts on sex changed?
22- Do you have any birth marks? How about scars? Care to share how you got them?
17- Have you ever done drugs? Which ones? How often?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
15~ Have you ever been “in love”? Who? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Do you think this brought you closer together?
48~ Do you have any siblings? Are you close to your family?
12- What’s your favorite food? What’s your least favorite?
* Give a rating for each one (0-100)
7- What if a person smells a certain way? 8- How about smoking?
61~ How willing would you be to try new sexual positions?
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?
Have you ever? Care to Share?
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?
8- What are your thoughts on politics?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
If NO, would you ever have one? Would it be with 2 men or 2 women?
9- What’s your favorite season and why? What’s your least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
38~ Share your most embarrassing sexual memory?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
10~ How many dates are necessary before you to have sex with someone?
How old are you? Male or Female?
52~ What are your hobbies?
13- What is the craziest/scariest thing you've ever done?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Repairman/Lonely Wife Virgin/Experienced
Would you do it again, and would you rather 2 females or 2 males?
9~ How many times over your lifetime do you think you have had sex so far?
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?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Does the thought excite you? Care to share?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
62~ Have you used adult toys?
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Do you have a favorite? Is it ok if your partner does?
3- What Superhero or Superpower would you want to be/have?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
31- If given a chance to be immortal, would you take it? Why?
51~ Are you willing to play adult games with your partner?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
1- What’s your favorite animal? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
What have you learned about yourself that you did not before this?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
36~ What is your favorite time of day to have sex/make love?
Nothing too Serious
40~ What’s the weirdest place you’ve ever had sex?
83~ How do you feel about Porn?
15- What bad habit do you wish you could quit? Do you have any addictions?
22- What is your favorite childhood memory? What is your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
92~ Have you ever had or have an STD? How many? What was it?
Teacher/Student Stranger/One Night Stand
15- What's your favorite saying? What word or phrase is your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
25~ How do you feel about PDA? (Public Display of Affection)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
49~ How many times have you been married? Why did they end?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Would you read them together?
8- What's your favorite flavor of ice cream? Do you a least favorite?
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?
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~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Prisoner/Prison Guard Landlord/Tenant
65~ Describe the best orgasm you’ve ever had? Care to share?
21- What's your favorite way to spend a weekend or time off?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
76~ Have you had a threesome? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
Master/Slave Boss/Maid
If yes, what?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
How many times do you think you have “made love”?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
The Ice Breaker Questions
80~ Share your top three fantasies/desires. (Be detailed) 😊
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
4- For a pet, Cat, dog or other?
30~ What's something unexpected that turns you on?
1- What was your first impression of me? Has it changed?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Do you like it when they show and tell you what they want?
6- Do you have dreams? Can you remember them? What do you usually dream about?
1~ How old were you when you had your first kiss? Who? Care to Share?
If you win, what will you make them do?
10- List 5 of your top pet peeves.
82~ Do you have any fantasies involving Role-Playing?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
81~ Do you have any kinks and/or fetishes?
Please share Did you stop?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
12- What is the weirdest thing you've ever eaten?
If you say it, I will stop, and we can talk about it when you are ready.
10- What is your favorite family tradition? What’s your least favorite?
89~ Do you like taking showers together?
44~ Care to share something about yourself that no one else knows about you?
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?
Doctor/Nurse Stripper/Client
42~ What’s your biggest regret in life?
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?
19~ Who/when was your first “heartbreak”?
11- What's your favorite restaurant? What’s your least favorite?
37- Do you like your name? If you could change it, what would you change it too?
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,
(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?
33- If you could visit any time period, when would you pick? Please explain why?
50~ How many children do you have? What are their ages?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
18- How often do you drink alcohol? What is your favorite drink?
14- What's your favorite dessert? Do you a least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
67~ Do you like it when your partner moans and/or is vocal during sex?
3- Should Pluto still be considered a planet? 4- How about smoking?
36- Do you play video games? What is your favorite? Do you a least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
9- If you could have three wishes, what would they be? Why?
Escort/Client Job Applicant/Hiring Manager
Family Relation Age Play
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
11~ Have you ever been caught by your parents or children or others while having sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
92~ Everyone needs a “safe” word. What is yours?
39~ What are your love languages?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
3- What’s your favorite smell? Do you a least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What is your favorite position? Why?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
34~ Do you like the lights on or off during sex?
Any that are a turn off?
19- Do/have you smoked? What do you prefer? How often?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
2- What’s your favorite color? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
19- What’s your favorite fairytale? What’s your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
(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…)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
*** Random Questions ***
49~ If you could, would you want to be the opposite sex for a day, week, or year?
18~ Who/when was your first “crush”?
21~ What was the best date you ever went on? What has been the worst?
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.
Nurse/Patient Celebrity/Fan
51~ What tends to bring a smile to your face?
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)
If YES, was it with 2 men or 2 women? Did you enjoy it?
What was the longest? What was the shortest?
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?
How about if they talk dirty and/or call you names?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?