What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 15:53
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Please share Did you stop?
Why do I sweat between my legs all the time, top off my legs, all way down?
80~ Share your top three fantasies/desires. (Be detailed) đ
8- What's your favorite flavor of ice cream? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
That one or two things that made you go hmmmm, OMG or wow!
7- What are your thoughts on religion? Is there an afterlife?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Have you ever been forced to undress for money just once?
70~ Would/do you have/like anal sex?
*** Random Questions ***
Model/Photographer Police/Criminal
Is heroin really as good as people say it is?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Why do some straight men like to suck dick but don't find other males attractive?
71~ Would you give your partner a hand or foot job? Would you receive one?
What is your view on sex? Meaning, When/Where/ How often/
I would allow you to do it⌠What would you do to me?
Are rich people harder workers than poor people as a whole?
You know that I will be 100% truthful, so ask.
How well do you know me? And some of your thoughts about me
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
7- What if a person smells a certain way? 8- How about smoking?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŚ
How do you feel about the impending end of what Donald Trump calls "the Green New scam"?
The Ice Breaker Questions
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
26~ What side of the bed do you sleep on?
Former Packers WR makes long touchdown in UFL championship - Acme Packing Company
How about if they talk dirty and/or call you names?
27- What was/ is nickname? Does it have a meaning behind it?
37- Do you like your name? If you could change it, what would you change it too?
Teens like me, what are your expectations when entering adulthood?
10- What is your favorite family tradition? Whatâs your least favorite?
Do you think this brought you closer together?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
If you win, what will you make them do?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Protester shot and killed at âNo Kingsâ rally in Utah, police say - AP News
92~ Everyone needs a âsafeâ word. What is yours?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
17- Whatâs your favorite holiday? Whatâs your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
17- Have you ever done drugs? Which ones? How often?
What do you dislike about me? I asked you to be 100% honest.
10~ How many dates are necessary before you to have sex with someone?
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
82~ Do you have any fantasies involving Role-Playing?
51~ Are you willing to play adult games with your partner?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
*** Questions about Relationships/Past ***
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,
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
29- How superstitious are you?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
89~ Do you like taking showers together?
9- If you could have three wishes, what would they be? Why?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
Over time has your thoughts on sex changed?
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?
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)
19~ Who/when was your first âheartbreakâ?
15- What bad habit do you wish you could quit? Do you have any addictions?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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 clean every part of your body with my soapy hands and fingers?
32- What's your greatest talent? Can I see it right now?
3- What was the most surprising thing youâve learned about me throughout our relationship?
Will you cheat again? How can, you be sure? Define what cheating is to you.
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you like it when they show and tell you what they want?
65~ Describe the best orgasm youâve ever had? Care to share?
Repairman/Lonely Wife Virgin/Experienced
1- What was your first impression of me? Has it changed?
Do you watch it? What is your favorite?
Do you have a favorite? Is it ok if your partner does?
19- Do/have you smoked? What do you prefer? How often?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
What have you learned about me that was new and/or surprising?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
83~ How do you feel about Porn?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
36- Do you play video games? What is your favorite? Do you a least favorite?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
*** Deal Breaker Questions ***
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŚ
11- List at least 5 things on your bucket list. Have you done any of them already?
How many partners have you had oral sex with? Who? Care to Share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
38~ Share your most embarrassing sexual memory?
61~ How willing would you be to try new sexual positions?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
9- Whatâs your favorite season and why? Whatâs your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything⌠Shave meâŚ
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
20- Whatâs your favorite candy? Whatâs your least favorite?
76~ Have you had a threesome? Care to Share?
1~ How old were you when you had your first kiss? Who? Care to Share?
Does the thought excite you? Care to share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
12- Whatâs your favorite food? Whatâs your least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
47~ What would be your dream job and why?
Teacher/Student Stranger/One Night Stand
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What have you learned about yourself that you did not before this?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
What would you say to prove to yourself that it was really you?
25~ How do you feel about PDA? (Public Display of Affection)
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Would you read them together?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
40~ Whatâs the weirdest place youâve ever had sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
3- Whatâs your favorite smell? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Escort/Client Job Applicant/Hiring Manager
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?
7-What do I do in bed that drives you wild? How about, what turns you off?
21- What's your favorite way to spend a weekend or time off?
33- If you could visit any time period, when would you pick? Please explain why?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
92~ Have you ever had or have an STD? How many? What was it?
3- What Superhero or Superpower would you want to be/have?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
8- What are your thoughts on politics?
51~ What tends to bring a smile to your face?
28- What are some things that people do that irritate you?
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
Would you mind if your partner watched it? How about together vs alone?
4- For a pet, Cat, dog or other?
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?
50~ How many children do you have? What are their ages?
15- What's your favorite saying? What word or phrase is your least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
14- What is an embarrassing moment in your life? How about your most embarrassing?
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
21~ What was the best date you ever went on? What has been the worst?
11- How about if they like a certain sports team? 12-How about drinking too much?
11~ Have you ever been caught by your parents or children or others while having sex?
Nurse/Patient Celebrity/Fan
39~ What are your love languages?
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
How many times do you think you have âmade loveâ?
Take the short quiz here @ Discover Your Love LanguageÂŽ - The 5 Love LanguagesÂŽ
22- What is your favorite childhood memory? What is your least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Prisoner/Prison Guard Landlord/Tenant
Can you Deep Throat? Do you like the taste of yourself?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
*** Whatâs Your FavoriteâŚ? ***
30~ What's something unexpected that turns you on?
Would you ever want to be woken up with oral and/or intercourse?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
*** Questions About Me ***
If NO, would you ever have one? Would it be with 2 men or 2 women?
13- How about having a certain hair cut/style?
1- Whatâs your favorite animal? Do you a least favorite?
18~ Who/when was your first âcrushâ?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
13- Whatâs your favorite drink? Whatâs your least favorite?
Master/Slave Boss/Maid
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
42~ Whatâs your biggest regret in life?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
13- What is the craziest/scariest thing you've ever done?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What is your favorite toy? Ever wanted to try a specific toy?
2- Whatâs your favorite color? Do you a least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
84~ How do you feel about reading/listening to adult stories?
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)
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
Any that are a turn off?
52~ Are you willing to make âthose typesâ of bets with your partner?
28~ What are some things that turn on? What is your biggest turn on?
11- What's your favorite restaurant? Whatâs your least favorite?
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
Get this wrong and this could mean the end⌠:-) some funny, some notâŚ
48~ Do you have any siblings? Are you close to your family?
14- What's your favorite dessert? Do you a least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Do you like the â69â position? Do you prefer to be on top or bottom?
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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
Would /have you ever given your partner a lap dance and Striptease?
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?
34~ Do you like the lights on or off during sex?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
10- List 5 of your top pet peeves.
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- Is there something youâve always wanted to ask me but youâre afraid?
49~ How many times have you been married? Why did they end?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
(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)
5~ When you first started having sex, was it what you thought it would be?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
15~ Have you ever been âin loveâ? Who? Care to Share?
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
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
* Give a rating for each one (0-100)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
Family Relation Age Play
60~ How important is oral sex? Do you like receiving? Do you like giving?
3- Should Pluto still be considered a planet? 4- How about smoking?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
23- What is your dream job? What was it as a child?
36~ What is your favorite time of day to have sex/make love?
If you say it, I will stop, and we can talk about it when you are ready.
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Nothing too Serious
Would you do it again, and would you rather 2 females or 2 males?
19- Whatâs your favorite fairytale? Whatâs your least favorite?
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?
29~ What are some things that turn you off? What is your biggest turn off?
What was the longest? What was the shortest?
18- How often do you drink alcohol? What is your favorite drink?
12- What is the weirdest thing you've ever eaten?
44~ Care to share something about yourself that no one else knows about you?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
If yes, what?
81~ Do you have any kinks and/or fetishes?
52~ What are your hobbies?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
13~ Is there a difference between, making love, having sex, and fucking?
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
31- If given a chance to be immortal, would you take it? Why?
What is your favorite position? Why?
62~ Have you used adult toys?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
5- Have you ever been hypnotized? Would you allow yourself to be?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Have you ever? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
67~ Do you like it when your partner moans and/or is vocal during sex?
How old are you? Male or Female?