What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 03:53
If yes, what?
25~ How do you feel about PDA? (Public Display of Affection)
7- What if a person smells a certain way? 8- How about smoking?
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62~ Have you used adult toys?
Please share Did you stop?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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If you say it, I will stop, and we can talk about it when you are ready.
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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)
Heart Disease: What You Eat Matters More Than Cutting Carbs, Fat - Healthline
45~ How do you feel about me blindfolding you? How about blindfolding me?
Will you cheat again? How can, you be sure? Define what cheating is to you.
The Ice Breaker Questions
What do feminists mean when they say they want to ‘normalize’ menstruation and its discussion?
83~ How do you feel about Porn?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
34- Ever been to a concert? What was your favorite? Who would you like to see?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Nurse/Patient Celebrity/Fan
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Can you Deep Throat? Do you like the taste of yourself?
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's your favorite flavor of ice cream? Do you a least favorite?
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3- What was the most surprising thing you’ve learned about me throughout our relationship?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
4- For a pet, Cat, dog or other?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
17- What’s your favorite holiday? What’s your least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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18~ Who/when was your first “crush”?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
9~ How many times over your lifetime do you think you have had sex so far?
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Have you ever? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
51~ What tends to bring a smile to your face?
Which other countries have implemented home appliance trade-in schemes?
92~ Have you ever had or have an STD? How many? What was it?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you think this brought you closer together?
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89~ Do you like taking showers together?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
I am a copy and paste developer, how do I become a real software developer?
9- Is there something you’ve always wanted to ask me but you’re afraid?
3- Should Pluto still be considered a planet? 4- How about smoking?
What have you learned about yourself that you did not before this?
1- What was your first impression of me? Has it changed?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
9- What’s your favorite season and why? What’s your least favorite?
What was the longest? What was the shortest?
Nothing too Serious
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
What is your favorite toy? Ever wanted to try a specific toy?
65~ Describe the best orgasm you’ve ever had? Care to share?
Would you ever want to be woken up with oral and/or intercourse?
40~ What’s the weirdest place you’ve ever had sex?
15~ Have you ever been “in love”? Who? Care to Share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
31- If given a chance to be immortal, would you take it? Why?
60~ How important is oral sex? Do you like receiving? Do you like giving?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
28- What are some things that people do that irritate you?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
*** Random Questions ***
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
How about if they talk dirty and/or call you names?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
1- What’s your favorite animal? Do you a least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
Would /have you ever given your partner a lap dance and Striptease?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
29- How superstitious are you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Family Relation Age Play
15- What bad habit do you wish you could quit? Do you have any addictions?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
How many partners have you had oral sex with? Who? Care to Share?
61~ How willing would you be to try new sexual positions?
36~ What is your favorite time of day to have sex/make love?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
Any that are a turn off?
Do you like it when they show and tell you what they want?
27- What was/ is nickname? Does it have a meaning behind it?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Does the thought excite you? Care to share?
3- What Superhero or Superpower would you want to be/have?
53~ How much can you tell me about the one thing you are most passionate about?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
76~ Have you had a threesome? Care to Share?
(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…)
Do you like the “69” position? Do you prefer to be on top or bottom?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
10~ How many dates are necessary before you to have sex with someone?
19- Do/have you smoked? What do you prefer? How often?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
5- Have you ever been hypnotized? Would you allow yourself to be?
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…
34~ Do you like the lights on or off during sex?
80~ Share your top three fantasies/desires. (Be detailed) 😊
24~ What are your expectations in a relationship? (I know a very big question, take your time)
11- List at least 5 things on your bucket list. Have you done any of them already?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
82~ Do you have any fantasies involving Role-Playing?
19- What’s your favorite fairytale? What’s your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
33- If you could visit any time period, when would you pick? Please explain why?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
10- What is your favorite family tradition? What’s your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
8- What are your thoughts on politics?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
21~ What was the best date you ever went on? What has been the worst?
51~ Are you willing to play adult games with your partner?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Get this wrong and this could mean the end… :-) some funny, some not…
21- What's your favorite way to spend a weekend or time off?
*** Questions about Relationships/Past ***
Model/Photographer Police/Criminal
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
How many times do you think you have “made love”?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
What have you learned about me that was new and/or surprising?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Any that are a turn off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
30~ What's something unexpected that turns you on?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
Master/Slave Boss/Maid
52~ Are you willing to make “those types” of bets with your partner?
13- What is the craziest/scariest thing you've ever done?
Repairman/Lonely Wife Virgin/Experienced
If you win, what will you make them do?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
47~ What would be your dream job and why?
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’s the longest time you gone without having sex, after, having it? How much time between the others?
Do you have a favorite? Is it ok if your partner does?
3- What’s your favorite smell? Do you a least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Teacher/Student Stranger/One Night Stand
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?
38~ Share your most embarrassing sexual memory?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
What do you dislike about me? I asked you to be 100% honest.
48~ Do you have any siblings? Are you close to your family?
1~ How old were you when you had your first kiss? Who? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
39~ What are your love languages?
23- What is your dream job? What was it as a child?
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~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
*** Deal Breaker Questions ***
7- What are your thoughts on religion? Is there an afterlife?
13- How about having a certain hair cut/style?
92~ Everyone needs a “safe” word. What is yours?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Escort/Client Job Applicant/Hiring Manager
84~ How do you feel about reading/listening to adult stories?
50~ How many children do you have? What are their ages?
70~ Would/do you have/like anal sex?
42~ What’s your biggest regret in life?
81~ Do you have any kinks and/or fetishes?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
12- What’s your favorite food? What’s your least favorite?
That one or two things that made you go hmmmm, OMG or wow!
*** What’s Your Favorite…? ***
19~ Who/when was your first “heartbreak”?
What would you say to prove to yourself that it was really you?
29~ What are some things that turn you off? What is your biggest turn off?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
17- Have you ever done drugs? Which ones? How often?
Would you mind if your partner watched it? How about together vs alone?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
10- List 5 of your top pet peeves.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
52~ What are your hobbies?
Would you read them together?
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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
How well do you know me? And some of your thoughts about me
26~ What side of the bed do you sleep on?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Doctor/Nurse Stripper/Client
You know that I will be 100% truthful, so ask.
* Give a rating for each one (0-100)
20- What’s your favorite candy? What’s your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
11- What's your favorite restaurant? What’s your least favorite?
Over time has your thoughts on sex changed?
37- Do you like your name? If you could change it, what would you change it too?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
I would allow you to do it… What would you do to me?
6- Do you have dreams? Can you remember them? What do you usually dream about?
How old are you? Male or Female?
71~ Would you give your partner a hand or foot job? Would you receive one?
What is your favorite position? Why?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
36- Do you play video games? What is your favorite? Do you a least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
11~ Have you ever been caught by your parents or children or others while having sex?
49~ How many times have you been married? Why did they end?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
5~ When you first started having sex, was it what you thought it would be?
Would you do it again, and would you rather 2 females or 2 males?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
12- What is the weirdest thing you've ever eaten?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
*** Questions About Me ***
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
9- If you could have three wishes, what would they be? Why?
13~ Is there a difference between, making love, having sex, and fucking?
44~ Care to share something about yourself that no one else knows about you?
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?
33- Beach or Mountains? Or is there another place to like better?
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?
14- What's your favorite dessert? Do you a least favorite?
18- How often do you drink alcohol? What is your favorite drink?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
2- What’s your favorite color? Do you a least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you watch it? What is your favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
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?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
13- What’s your favorite drink? What’s your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
30- Do you prefer living in the countryside, in a town, or in a big city? 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…
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
48~ Have you ever paid or been paid for sex?
Prisoner/Prison Guard Landlord/Tenant