What is the most interesting question you can ask to get to know someone?
Last Updated: 24.06.2025 01:17
(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…)
17- What’s your favorite holiday? What’s your least favorite?
1- What was your first impression of me? Has it changed?
Ad eveniet eaque et magni illum.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
38~ Share your most embarrassing sexual memory?
13- What’s your favorite drink? What’s your least favorite?
A chemical in acne medicine can help regenerate limbs - Yahoo
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Model/Photographer Police/Criminal
36~ What is your favorite time of day to have sex/make love?
How will the newly imposed trade tariffs affect the global economy?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
*** Random Questions ***
49~ How many times have you been married? Why did they end?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Any that are a turn off?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What are some small, random things that annoy you to no end?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Would you allow me to clean every part of your body with my soapy hands and fingers?
40~ What’s the weirdest place you’ve ever had sex?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
New Study Finds 1 Promising Way To Keep Colon Cancer From Returning - HuffPost
81~ Do you have any kinks and/or fetishes?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
Why did you put a guy’s dick in your mouth the first time?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Can you Deep Throat? Do you like the taste of yourself?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What are some funny stories of people calling 911 for non-emergencies?
What is your favorite position? Why?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
The ‘golden summer of cheap flights’: Now’s the time for last-minute deals - CNN
Do you think this brought you closer together?
I would allow you to do it… What would you do to me?
*** Questions About Me ***
What was the longest? What was the shortest?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Sunt accusamus voluptates dolorem porro excepturi quis officiis facere.
25~ How do you feel about PDA? (Public Display of Affection)
33- If you could visit any time period, when would you pick? Please explain why?
Will you cheat again? How can, you be sure? Define what cheating is to you.
If yes, what?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
48~ Have you ever paid or been paid for sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
8- What are your thoughts on politics?
14- What's your favorite dessert? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
Would you ever want to be woken up with oral and/or intercourse?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
5~ When you first started having sex, was it what you thought it would be?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Teacher/Student Stranger/One Night Stand
11- List at least 5 things on your bucket list. Have you done any of them already?
27- What was/ is nickname? Does it have a meaning behind it?
22- What is your favorite childhood memory? What is your least favorite?
3- What’s your favorite smell? Do you a least favorite?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
11- How about if they like a certain sports team? 12-How about drinking too much?
Have you ever? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
If you say it, I will stop, and we can talk about it when you are ready.
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
12- What is the weirdest thing you've ever eaten?
Would you read them together?
7- What are your thoughts on religion? Is there an afterlife?
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?
23- What is your dream job? What was it as a child?
29- How superstitious are you?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
31- If given a chance to be immortal, would you take it? Why?
Does the thought excite you? Care to share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
The Ice Breaker Questions
80~ Share your top three fantasies/desires. (Be detailed) 😊
*** What’s Your Favorite…? ***
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Family Relation Age Play
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
32- What's your greatest talent? Can I see it right now?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
16~ Do you believe in “soulmates”? Have you found yours? Who? 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?
Get this wrong and this could mean the end… :-) some funny, some not…
84~ How do you feel about reading/listening to adult stories?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Escort/Client Job Applicant/Hiring Manager
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
1- What’s your favorite animal? Do you a least favorite?
28~ What are some things that turn on? What is your biggest turn on?
11- What's your favorite restaurant? What’s your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
76~ Have you had a threesome? Care to Share?
12- What’s your favorite food? What’s your least favorite?
42~ What’s your biggest regret in life?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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?
19- Do/have you smoked? What do you prefer? How often?
How old are you? Male or Female?
10~ How many dates are necessary before you to have sex with someone?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What have you learned about yourself that you did not before this?
34~ Do you like the lights on or off during sex?
9- What’s your favorite season and why? What’s your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
89~ Do you like taking showers together?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
70~ Would/do you have/like anal sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
20- What’s your favorite candy? What’s your least favorite?
* Give a rating for each one (0-100)
1~ How old were you when you had your first kiss? Who? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Nothing too Serious
51~ What tends to bring a smile to your face?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
Prisoner/Prison Guard Landlord/Tenant
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…
Doctor/Nurse Stripper/Client
Would /have you ever given your partner a lap dance and Striptease?
9- If you could have three wishes, what would they be? Why?
44~ Care to share something about yourself that no one else knows about you?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
That one or two things that made you go hmmmm, OMG or wow!
10- List 5 of your top pet peeves.
7-What do I do in bed that drives you wild? How about, what turns you off?
21~ What was the best date you ever went on? What has been the worst?
18- How often do you drink alcohol? What is your favorite drink?
What is your favorite toy? Ever wanted to try a specific toy?
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,
37- Do you like your name? If you could change it, what would you change it too?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
62~ Have you used adult toys?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
5- Have you ever been hypnotized? Would you allow yourself to be?
8- What's your favorite flavor of ice cream? Do you a least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
If you win, what will you make them do?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
How well do you know me? And some of your thoughts about me
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?
Do you have a favorite? Is it ok if your partner does?
60~ How important is oral sex? Do you like receiving? Do you like giving?
6- Do you have dreams? Can you remember them? What do you usually dream about?
9~ How many times over your lifetime do you think you have had sex so far?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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?
7- What if a person smells a certain way? 8- How about smoking?
83~ How do you feel about Porn?
14- What is an embarrassing moment in your life? How about your most embarrassing?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
21- What's your favorite way to spend a weekend or time off?
28- What are some things that people do that irritate you?
47~ What would be your dream job and why?
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…
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
If YES, was it with 2 men or 2 women? Did you enjoy it?
92~ Everyone needs a “safe” word. What is yours?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
39~ What are your love languages?
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?
How about if they talk dirty and/or call you names?
33- Beach or Mountains? Or is there another place to like better?
18~ Who/when was your first “crush”?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
4- For a pet, Cat, dog or other?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Would you mind if your partner watched it? How about together vs alone?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
*** Questions about Relationships/Past ***
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?
53~ How much can you tell me about the one thing you are most passionate about?
52~ What are your hobbies?
Nurse/Patient Celebrity/Fan
15- What bad habit do you wish you could quit? Do you have any addictions?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
50~ How many children do you have? What are their ages?
Please share Did you stop?
*** Deal Breaker Questions ***
61~ How willing would you be to try new sexual positions?
What would you say to prove to yourself that it was really you?
36- Do you play video games? What is your favorite? Do you a least favorite?
Would you do it again, and would you rather 2 females or 2 males?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
48~ Do you have any siblings? Are you close to your family?
19~ Who/when was your first “heartbreak”?
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
Do you like it when they show and tell you what they want?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
17- Have you ever done drugs? Which ones? How often?
34- Ever been to a concert? What was your favorite? Who would you like to see?
82~ Do you have any fantasies involving Role-Playing?
Over time has your thoughts on sex changed?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
What have you learned about me that was new and/or surprising?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
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?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How many partners have you had oral sex with? Who? Care to Share?
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.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
15~ Have you ever been “in love”? Who? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
You know that I will be 100% truthful, so ask.
92~ Have you ever had or have an STD? How many? What was it?
How many times do you think you have “made love”?
71~ Would you give your partner a hand or foot job? Would you receive one?
3- What Superhero or Superpower would you want to be/have?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
26~ What side of the bed do you sleep on?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What do you dislike about me? I asked you to be 100% honest.
13- What is the craziest/scariest thing you've ever done?
13- How about having a certain hair cut/style?
What is your view on sex? Meaning, When/Where/ How often/
Any that are a turn off?
30~ What's something unexpected that turns you on?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
Master/Slave Boss/Maid
9- Is there something you’ve always wanted to ask me but you’re afraid?
2- What’s your favorite color? Do you a least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Do you watch it? What is your favorite?
51~ Are you willing to play adult games with your partner?
67~ Do you like it when your partner moans and/or is vocal during sex?