What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 05:33
80~ Share your top three fantasies/desires. (Be detailed) đ
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Why do I sweat between my legs all the time, top off my legs, all way down?
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
85~ If you gave me a âfree Passâ to have me do anything for one hour, what would you want me to do to you?
Get this wrong and this could mean the end⌠:-) some funny, some notâŚ
Why is going on a date today so much different than it was when I was young?
9~ How many times over your lifetime do you think you have had sex so far?
Would you read them together?
29- How superstitious are you?
Is dating in college necessary? Why and why not?
*** Whatâs Your FavoriteâŚ? ***
25~ How do you feel about PDA? (Public Display of Affection)
12- What is the weirdest thing you've ever eaten?
States With the Most Generous Tippers - Newser
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŚ
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What is a fun psychological trick to try on someone?
83~ How do you feel about Porn?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
33- If you could visit any time period, when would you pick? Please explain why?
Iâm 17 and looking for a girl. What do I do?
48~ Do you have any siblings? Are you close to your family?
71~ Would you give your partner a hand or foot job? Would you receive one?
What do you dislike about me? I asked you to be 100% honest.
Why is every human messed up in some way?
*** Questions About Me ***
15- What bad habit do you wish you could quit? Do you have any addictions?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Why is our generation so unhappy?
67~ Do you like it when your partner moans and/or is vocal during sex?
1- Whatâs your favorite animal? Do you a 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?
Why is social media so anti-fee speech, and have they become total BS?
48~ Have you ever paid or been paid for sex?
13- How about having a certain hair cut/style?
65~ Describe the best orgasm youâve ever had? Care to share?
Why do people always talk about Ohio as it's a dangerous city?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
11- What's your favorite restaurant? Whatâs your least favorite?
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
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?
18~ Who/when was your first âcrushâ?
15- What's your favorite saying? What word or phrase 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?
Any that are a turn off?
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10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you like it when they show and tell you what they want?
21- What's your favorite way to spend a weekend or time off?
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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?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What are some funny stories of people calling 911 for non-emergencies?
38~ Share your most embarrassing sexual memory?
44~ Care to share something about yourself that no one else knows about you?
What would you say to prove to yourself that it was really you?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Does the thought excite you? Care to share?
5- Have you ever been hypnotized? Would you allow yourself to be?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
3- What Superhero or Superpower would you want to be/have?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
36~ What is your favorite time of day to have sex/make love?
1~ How old were you when you had your first kiss? Who? Care to Share?
76~ Have you had a threesome? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
* Give a rating for each one (0-100)
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Teacher/Student Stranger/One Night Stand
Repairman/Lonely Wife Virgin/Experienced
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?
Prisoner/Prison Guard Landlord/Tenant
19~ Who/when was your first âheartbreakâ?
Please share Did you stop?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
51~ Are you willing to play adult games with your partner?
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?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Master/Slave Boss/Maid
15~ Have you ever been âin loveâ? Who? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Nurse/Patient Celebrity/Fan
If you win, what will you make them do?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
22- What is your favorite childhood memory? What is your least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
11~ Have you ever been caught by your parents or children or others while having sex?
50~ How many children do you have? What are their ages?
4- For a pet, Cat, dog or other?
13- What is the craziest/scariest thing you've ever done?
Escort/Client Job Applicant/Hiring Manager
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If you say it, I will stop, and we can talk about it when you are ready.
Any that are a turn off?
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?
5~ When you first started having sex, was it what you thought it would be?
Do you have a favorite? Is it ok if your partner does?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
19- Whatâs your favorite fairytale? Whatâs your least favorite?
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
10- What is your favorite family tradition? Whatâs your least favorite?
Would /have you ever given your partner a lap dance and Striptease?
34- Ever been to a concert? What was your favorite? Who would you like to see?
What is your favorite position? Why?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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?
Model/Photographer Police/Criminal
17- Whatâs your favorite holiday? Whatâs your least favorite?
19- Do/have you smoked? What do you prefer? How often?
31- If given a chance to be immortal, would you take it? 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 togetherâŚ
28- What are some things that people do that irritate you?
Doctor/Nurse Stripper/Client
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If YES, was it with 2 men or 2 women? Did you enjoy it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
47~ What would be your dream job and why?
Family Relation Age Play
How well do you know me? And some of your thoughts about me
36- Do you play video games? What is your favorite? Do you a least favorite?
7- What if a person smells a certain way? 8- How about smoking?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
26~ What side of the bed do you sleep on?
3- Whatâs your favorite smell? Do you a least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? 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?
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?
*** Deal Breaker Questions ***
What have you learned about me that was new and/or surprising?
84~ How do you feel about reading/listening to adult stories?
What is your favorite toy? Ever wanted to try a specific toy?
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 ever want to be woken up with oral and/or intercourse?
10- List 5 of your top pet peeves.
92~ Have you ever had or have an STD? How many? What was it?
11- List at least 5 things on your bucket list. Have you done any of them already?
81~ Do you have any kinks and/or fetishes?
14 â Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Piecing, tattoo, color hair, dress up a certain way, it could be anything⌠Shave meâŚ
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?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
If NO, would you ever have one? Would it be with 2 men or 2 women?
28~ What are some things that turn on? What is your biggest turn on?
89~ Do you like taking showers together?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What was the longest? What was the shortest?
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?
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
62~ Have you used adult toys?
*** Random Questions ***
What is your view on sex? Meaning, When/Where/ How often/
70~ Would/do you have/like anal sex?
10~ How many dates are necessary before you to have sex with someone?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
92~ Everyone needs a âsafeâ word. What is yours?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
12- Whatâs your favorite food? Whatâs your least favorite?
Do you like the â69â position? Do you prefer to be on top or bottom?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
14- Do you have a âDeal Breakerâ, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
Take the short quiz here @ Discover Your Love LanguageÂŽ - The 5 Love LanguagesÂŽ
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couplesâ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETCâŚ)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Would you allow me to clean every part of your body with my soapy hands and fingers?
49~ How many times have you been married? Why did they end?
34~ Do you like the lights on or off during sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Nothing too Serious
14- What's your favorite dessert? Do you a least favorite?
3- What was the most surprising thing youâve learned about me throughout our relationship?
52~ What are your hobbies?
23- What is your dream job? What was it as a child?
45~ How do you feel about me blindfolding you? How about blindfolding me?
That one or two things that made you go hmmmm, OMG or wow!
How many times do you think you have âmade loveâ?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
21~ What was the best date you ever went on? What has been the worst?
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŚ
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
85~ If I gave you a âFree Passâ for you to do anything to me for one hour, knowing that no matter what you did,
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
*** Questions about Relationships/Past ***
2- Whatâs your favorite color? Do you a least favorite?
82~ Do you have any fantasies involving Role-Playing?
20- Whatâs your favorite candy? Whatâs your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
9- If you could have three wishes, what would they be? Why?
40~ Whatâs the weirdest place youâve ever had sex?
17- Have you ever done drugs? Which ones? How often?
What have you learned about yourself that you did not before this?
61~ How willing would you be to try new sexual positions?
33- Beach or Mountains? Or is there another place to like better?
9- Is there something youâve always wanted to ask me but youâre afraid?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
7-What do I do in bed that drives you wild? How about, what turns you off?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
13- Whatâs your favorite drink? Whatâs your least favorite?
Would you mind if your partner watched it? How about together vs alone?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
How about if they talk dirty and/or call you names?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
How many partners have you had oral sex with? Who? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
27- What was/ is nickname? Does it have a meaning behind it?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
13~ Is there a difference between, making love, having sex, and fucking?
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
8- What are your thoughts on politics?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
8- What's your favorite flavor of ice cream? Do you a least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
1- What was your first impression of me? Has it changed?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
53~ How much can you tell me about the one thing you are most passionate about?
I would allow you to do it⌠What would you do to me?
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 âPASSâ 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 yourselfâŚ
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
The Ice Breaker Questions
52~ Are you willing to make âthose typesâ of bets with your partner?
Do you watch it? What is your favorite?
9- Whatâs your favorite season and why? Whatâs your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
42~ Whatâs your biggest regret in life?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Can you Deep Throat? Do you like the taste of yourself?
If yes, what?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
30~ What's something unexpected that turns you on?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How old are you? Male or Female?
You know that I will be 100% truthful, so ask.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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)
Do you think this brought you closer together?
51~ What tends to bring a smile to your face?
Over time has your thoughts on sex changed?
39~ What are your love languages?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?