What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 09:44
Have you ever? Care to Share?
8- What are your thoughts on politics?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
How do you help patients stop hearing voices?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Would you mind if your partner watched it? How about together vs alone?
Can you Deep Throat? Do you like the taste of yourself?
Do you find Anushka Sen attractive?
13~ Is there a difference between, making love, having sex, and fucking?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What made you feel disgusted today?
Any that are a turn off?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Why after 50 years of being straight do I constantly desire to suck cock?
13- What is the craziest/scariest thing you've ever done?
49~ How many times have you been married? Why did they end?
13- How about having a certain hair cut/style?
How do I come out as queer to my best friend in a funny and stupid way?
62~ Have you used adult toys?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
36- Do you play video games? What is your favorite? Do you a least favorite?
I have the power to talk to aliens through using telepathy. Why do people think I'm crazy?
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?
22- What is your favorite childhood memory? What is your least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
How do you take your erotic photos and how do you choose the poses?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
(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…)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
What have you learned about me that was new and/or surprising?
11- List at least 5 things on your bucket list. Have you done any of them already?
34~ Do you like the lights on or off during sex?
Is a man over 50 not married no kids a red flag?
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?
Repairman/Lonely Wife Virgin/Experienced
Does the thought excite you? Care to share?
Can supporters of gun control explain the purpose behind a gun registry?
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?
Teacher/Student Stranger/One Night Stand
How old are you? Male or Female?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
29~ What are some things that turn you off? What is your biggest turn off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
That one or two things that made you go hmmmm, OMG or wow!
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
3- What Superhero or Superpower would you want to be/have?
12- What’s your favorite food? What’s your least favorite?
30~ What's something unexpected that turns you on?
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?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Get this wrong and this could mean the end… :-) some funny, some not…
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,
3- What’s your favorite smell? Do you a least favorite?
*** Random Questions ***
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?
28- What are some things that people do that irritate you?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
How well do you know me? And some of your thoughts about me
52~ What are your hobbies?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
81~ Do you have any kinks and/or fetishes?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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…
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
4- For a pet, Cat, dog or other?
5~ When you first started having sex, was it what you thought it would be?
14- What is an embarrassing moment in your life? How about your most embarrassing?
61~ How willing would you be to try new sexual positions?
84~ How do you feel about reading/listening to adult stories?
33- If you could visit any time period, when would you pick? Please explain why?
Master/Slave Boss/Maid
51~ What tends to bring a smile to your face?
89~ Do you like taking showers together?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
How many times do you think you have “made love”?
Family Relation Age Play
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
53~ How much can you tell me about the one thing you are most passionate about?
5- Have you ever been hypnotized? Would you allow yourself to be?
Please share Did you stop?
92~ Everyone needs a “safe” word. What is yours?
33- Beach or Mountains? Or is there another place to like better?
I would allow you to do it… What would you do to me?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
19- Do/have you smoked? What do you prefer? How often?
17- Have you ever done drugs? Which ones? How often?
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
29- How superstitious are you?
48~ Have you ever paid or been paid for sex?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
What do you dislike about me? I asked you to be 100% honest.
34- Ever been to a concert? What was your favorite? Who would you like to see?
51~ Are you willing to play adult games with your partner?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Nurse/Patient Celebrity/Fan
15- What bad habit do you wish you could quit? Do you have any addictions?
10- What is your favorite family tradition? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
11~ Have you ever been caught by your parents or children or others while having sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
The Ice Breaker Questions
48~ Do you have any siblings? Are you close to your family?
Any that are a turn off?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
You know that I will be 100% truthful, so ask.
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
7- What are your thoughts on religion? Is there an afterlife?
*** Questions About Me ***
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
2- What’s your favorite color? Do you a least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
71~ Would you give your partner a hand or foot job? Would you receive one?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Do you have a favorite? Is it ok if your partner does?
11- What's your favorite restaurant? What’s your least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
50~ How many children do you have? What are their ages?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
*** What’s Your Favorite…? ***
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
*** Questions about Relationships/Past ***
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
How about if they talk dirty and/or call you names?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
36~ What is your favorite time of day to have sex/make love?
9- If you could have three wishes, what would they be? Why?
42~ What’s your biggest regret in life?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Do you watch it? What is your favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
76~ Have you had a threesome? Care to Share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Would /have you ever given your partner a lap dance and Striptease?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
21~ What was the best date you ever went on? What has been the worst?
25~ How do you feel about PDA? (Public Display of Affection)
Prisoner/Prison Guard Landlord/Tenant
44~ Care to share something about yourself that no one else knows about you?
Do you like the “69” position? Do you prefer to be on top or bottom?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
10~ How many dates are necessary before you to have sex with someone?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Do you think this brought you closer together?
Model/Photographer Police/Criminal
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
39~ What are your love languages?
Would you ever want to be woken up with oral and/or intercourse?
9- Is there something you’ve always wanted to ask me but you’re afraid?
92~ Have you ever had or have an STD? How many? What was it?
1- What’s your favorite animal? Do you a least favorite?
What was the longest? What was the shortest?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Over time has your thoughts on sex changed?
What is your favorite position? Why?
15- What's your favorite saying? What word or phrase is your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
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)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
37- Do you like your name? If you could change it, what would you change it too?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Would you read them together?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
9- What’s your favorite season and why? What’s your least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
Would you do it again, and would you rather 2 females or 2 males?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
If you win, what will you make them do?
11- How about if they like a certain sports team? 12-How about drinking too much?
32- What's your greatest talent? Can I see it right now?
What is your favorite toy? Ever wanted to try a specific toy?
20- What’s your favorite candy? What’s your least favorite?
31- If given a chance to be immortal, would you take it? Why?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Do you like it when they show and tell you what they want?
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
82~ Do you have any fantasies involving Role-Playing?
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?
Doctor/Nurse Stripper/Client
24~ What are your expectations in a relationship? (I know a very big question, take your time)
9~ How many times over your lifetime do you think you have had sex so far?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
If yes, what?
If you say it, I will stop, and we can talk about it when you are ready.
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
12- What is the weirdest thing you've ever eaten?
6- Do you have dreams? Can you remember them? What do you usually dream about?
22- Do you have any birth marks? How about scars? Care to share how you got them?
*** Deal Breaker Questions ***
70~ Would/do you have/like anal sex?
18~ Who/when was your first “crush”?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
38~ Share your most embarrassing sexual memory?
21- What's your favorite way to spend a weekend or time off?
60~ How important is oral sex? Do you like receiving? Do you like giving?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
40~ What’s the weirdest place you’ve ever had sex?
7-What do I do in bed that drives you wild? How about, what turns you off?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
18- How often do you drink alcohol? What is your favorite drink?
19~ Who/when was your first “heartbreak”?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you allow me to clean every part of your body with my soapy hands and fingers?
52~ Are you willing to make “those types” of bets with your partner?
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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What have you learned about yourself that you did not before this?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Escort/Client Job Applicant/Hiring Manager
What would you say to prove to yourself that it was really you?
83~ How do you feel about Porn?
67~ Do you like it when your partner moans and/or is vocal during sex?
80~ Share your top three fantasies/desires. (Be detailed) 😊
23- What is your dream job? What was it as a child?
27- What was/ is nickname? Does it have a meaning behind it?
Nothing too Serious
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…
47~ What would be your dream job and why?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
17- What’s your favorite holiday? What’s your least favorite?
1- What was your first impression of me? Has it changed?
How many partners have you had oral sex with? Who? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
8- What's your favorite flavor of ice cream? Do you a least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
* Give a rating for each one (0-100)
15~ Have you ever been “in love”? Who? Care to Share?
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?
10- List 5 of your top pet peeves.
19- What’s your favorite fairytale? What’s your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
28~ What are some things that turn on? What is your biggest turn on?
14- What's your favorite dessert? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?