What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 03:02

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