What is the most interesting question you can ask to get to know someone?
15.06.2025 02:17
7- What if a person smells a certain way? 8- How about smoking?
Master/Slave Boss/Maid
Will you cheat again? How can, you be sure? Define what cheating is to you.
Have you ever had your crush reject you, and then later you all dated and married?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Prisoner/Prison Guard Landlord/Tenant
4- For a pet, Cat, dog or other?
Do Republicans want to ban books and decide what your kids can and can’t read?
43~ Ever had your hair pulled 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?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
What would be the lowest score with 9 strikes and no gutter balls?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
3- What’s your favorite smell? Do you a least favorite?
Would you do it again, and would you rather 2 females or 2 males?
Why are white women dating more black guys than ever?
27- What was/ is nickname? Does it have a meaning behind it?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Can you tell me something about yourself?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
34- Ever been to a concert? What was your favorite? Who would you like to see?
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?
65~ Describe the best orgasm you’ve ever had? Care to share?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What would you say to prove to yourself that it was really you?
What do you dislike about me? I asked you to be 100% honest.
Have you ever? Care to Share?
13- How about having a certain hair cut/style?
Have you made a female relative or friend squirt?
13~ Is there a difference between, making love, having sex, and fucking?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
18- How often do you drink alcohol? What is your favorite drink?
The Earth Shook Every 90 Seconds for 9 Days in 2023 – Scientists Finally Know Why - SciTechDaily
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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?
21- What's your favorite way to spend a weekend or time off?
What caused the stock market to crash?
60~ How important is oral sex? Do you like receiving? Do you like giving?
36- Do you play video games? What is your favorite? Do you a least favorite?
32- What's your greatest talent? Can I see it right now?
What was the longest? What was the shortest?
15- What bad habit do you wish you could quit? Do you have any addictions?
Would you ever want to be woken up with oral and/or intercourse?
Why is Jack Smith arguing that presidents should not have full immunities as Trump is requesting?
If NO, would you ever have one? Would it be with 2 men or 2 women?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Nothing too Serious
What is your opinion about homosexuality? Do you think that it is by nature or a choice?
14- What is an embarrassing moment in your life? How about your most embarrassing?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
52~ What are your hobbies?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
28~ What are some things that turn on? What is your biggest turn on?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
The Ice Breaker Questions
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
50~ How many children do you have? What are their ages?
11- What's your favorite restaurant? What’s your least favorite?
*** Questions About Me ***
*** Questions about Relationships/Past ***
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
14- What's your favorite dessert? Do you a least favorite?
10- List 5 of your top pet peeves.
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)
19- Do/have you smoked? What do you prefer? How often?
17- Have you ever done drugs? Which ones? How often?
29- How superstitious are you?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
89~ Do you like taking showers together?
62~ Have you used adult toys?
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?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
2- What’s your favorite color? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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 together…
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…
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
84~ How do you feel about reading/listening to adult stories?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Family Relation Age Play
Doctor/Nurse Stripper/Client
If you lose, are you willing to be their sex slave for a day, (anything goes)?
What is your favorite position? Why?
38~ Share your most embarrassing sexual memory?
10- What is your favorite family tradition? What’s your least favorite?
Do you think this brought you closer together?
44~ Care to share something about yourself that no one else knows about you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
5~ When you first started having sex, was it what you thought it would be?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How many partners have you had oral sex with? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
39~ What are your love languages?
If yes, what?
Over time has your thoughts on sex changed?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
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,
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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?
92~ Everyone needs a “safe” word. What is yours?
47~ What would be your dream job and why?
33- If you could visit any time period, when would you pick? Please explain why?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
28- What are some things that people do that irritate you?
9- Is there something you’ve always wanted to ask me but you’re afraid?
20- What’s your favorite candy? What’s your least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
37- Do you like your name? If you could change it, what would you change it too?
83~ How do you feel about Porn?
22- What is your favorite childhood memory? What is your least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
92~ Have you ever had or have an STD? How many? What was it?
18~ Who/when was your first “crush”?
Would you mind if your partner watched it? How about together vs alone?
82~ Do you have any fantasies involving Role-Playing?
48~ Have you ever paid or been paid for sex?
51~ Are you willing to play adult games with your partner?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
42~ What’s your biggest regret in life?
9- If you could have three wishes, what would they be? Why?
Any that are a turn off?
15~ Have you ever been “in love”? Who? Care to Share?
What is your view on sex? Meaning, When/Where/ How often/
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
*** What’s Your Favorite…? ***
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
45~ How do you feel about me blindfolding you? How about blindfolding me?
1~ How old were you when you had your first kiss? Who? Care to Share?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
33- Beach or Mountains? Or is there another place to like better?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
51~ What tends to bring a smile to your face?
Get this wrong and this could mean the end… :-) some funny, some not…
13- What is the craziest/scariest thing you've ever done?
49~ How many times have you been married? Why did they end?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you watch it? What is your favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
15- What's your favorite saying? What word or phrase is your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
29~ What are some things that turn you off? What is your biggest turn off?
*** Deal Breaker Questions ***
70~ Would/do you have/like anal sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
11~ Have you ever been caught by your parents or children or others while having sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Escort/Client Job Applicant/Hiring Manager
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
61~ How willing would you be to try new sexual positions?
Can you Deep Throat? Do you like the taste of yourself?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
If you win, what will you make them do?
13- What’s your favorite drink? What’s your least favorite?
Would /have you ever given your partner a lap dance and Striptease?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
If you say it, I will stop, and we can talk about it when you are ready.
What is your favorite toy? Ever wanted to try a specific toy?
9~ How many times over your lifetime do you think you have had sex so far?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
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?
* Give a rating for each one (0-100)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
21~ What was the best date you ever went on? What has been the worst?
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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
10~ How many dates are necessary before you to have sex with someone?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
11- List at least 5 things on your bucket list. Have you done any of them already?
Would you read them together?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Do you like it when they show and tell you what they want?
Do you like the “69” position? Do you prefer to be on top or bottom?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
36~ What is your favorite time of day to have sex/make love?
19~ Who/when was your first “heartbreak”?
Does the thought excite you? Care to share?
You know that I will be 100% truthful, so ask.
30~ What's something unexpected that turns you on?
12- What’s your favorite food? What’s your least favorite?
That one or two things that made you go hmmmm, OMG or wow!
5- Have you ever been hypnotized? Would you allow yourself to be?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
8- What are your thoughts on politics?
Any that are a turn off?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What have you learned about yourself that you did not before this?
71~ Would you give your partner a hand or foot job? Would you receive one?
7- What are your thoughts on religion? Is there an afterlife?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
11- How about if they like a certain sports team? 12-How about drinking too much?
Model/Photographer Police/Criminal
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What have you learned about me that was new and/or surprising?
25~ How do you feel about PDA? (Public Display of Affection)
34~ Do you like the lights on or off during sex?
1- What was your first impression of me? Has it changed?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** Random Questions ***
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Teacher/Student Stranger/One Night Stand
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?
(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…)
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?
Do you have a favorite? Is it ok if your partner does?
26~ What side of the bed do you sleep on?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Nurse/Patient Celebrity/Fan
Will you kiss after your partner has gone down on you? Swallow or spit semen?
I would allow you to do it… What would you do to me?
76~ Have you had a threesome? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
48~ Do you have any siblings? Are you close to your family?
Would you allow me to clean every part of your body with my soapy hands and fingers?
23- What is your dream job? What was it as a child?
Repairman/Lonely Wife Virgin/Experienced
1- What’s your favorite animal? Do you a least favorite?
3- What Superhero or Superpower would you want to be/have?
Please share Did you stop?
81~ Do you have any kinks and/or fetishes?
How well do you know me? And some of your thoughts about me
9- What’s your favorite season and why? What’s your least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
52~ Are you willing to make “those types” of bets with your partner?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
How about if they talk dirty and/or call you names?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
How many times do you think you have “made love”?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
How old are you? Male or Female?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
If YES, was it with 2 men or 2 women? Did you enjoy it?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)