What is the most interesting question you can ask to get to know someone?
15.06.2025 01:06
What do you dislike about me? I asked you to be 100% honest.
12- What’s your favorite food? What’s your least favorite?
*** Questions about Relationships/Past ***
What is the dirtiest thing you have witnessed your wife do?
80~ Share your top three fantasies/desires. (Be detailed) 😊
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Was Michael Jackson really an innocent person?
Over time has your thoughts on sex changed?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
What's an uncomfortable truth you've learned to accept?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Would you mind if your partner watched it? How about together vs alone?
13- What is the craziest/scariest thing you've ever done?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
21- What's your favorite way to spend a weekend or time off?
What is an appropriate response to someone saying "merci" in French?
19- Do/have you smoked? What do you prefer? How often?
34- Ever been to a concert? What was your favorite? Who would you like to see?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
How do I rat my boss out for serial cheating on his wife?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Will Kamala Harris rekindle the business model of sleeping your way to the top?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Get this wrong and this could mean the end… :-) some funny, some not…
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?
Would you ever want to be woken up with oral and/or intercourse?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Nurse/Patient Celebrity/Fan
Why did my ex move on so quickly?
Please share Did you stop?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
What was your most memorable combat mission during the Vietnam War?
Family Relation Age Play
Can you Deep Throat? Do you like the taste of yourself?
89~ Do you like taking showers together?
Is there a specific time frame for therapists to tell their clients they are wrong?
*** Random Questions ***
15- What's your favorite saying? What word or phrase is your least favorite?
49~ How many times have you been married? Why did they end?
If you caught a shoplifter at your yard sale, how would you handle it?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
81~ Do you have any kinks and/or fetishes?
71~ Would you give your partner a hand or foot job? Would you receive one?
What are some prime examples of gibberish from the bible?
Teacher/Student Stranger/One Night Stand
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
How many times do you think you have “made love”?
Do you like it when they show and tell you what they want?
What was the longest? What was the shortest?
52~ Are you willing to make “those types” of bets with your partner?
11- How about if they like a certain sports team? 12-How about drinking too much?
48~ Do you have any siblings? Are you close to your family?
I would allow you to do it… What would you do to me?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
1- What was your first impression of me? Has it changed?
15- What bad habit do you wish you could quit? Do you have any addictions?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
*** What’s Your Favorite…? ***
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
How about if they talk dirty and/or call you names?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Escort/Client Job Applicant/Hiring Manager
36- Do you play video games? What is your favorite? Do you a least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
37- Do you like your name? If you could change it, what would you change it too?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
82~ Do you have any fantasies involving Role-Playing?
What have you learned about me that was new and/or surprising?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
28- What are some things that people do that irritate you?
11- What's your favorite restaurant? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
10~ How many dates are necessary before you to have sex with someone?
*** Deal Breaker Questions ***
What’s the longest time you gone without having sex, after, having it? How much time between the others?
33- If you could visit any time period, when would you pick? Please explain why?
18- How often do you drink alcohol? What is your favorite drink?
18~ Who/when was your first “crush”?
13- How about having a certain hair cut/style?
What is your view on sex? Meaning, When/Where/ How often/
51~ Are you willing to play adult games with your partner?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
17- Have you ever done drugs? Which ones? How often?
33- Beach or Mountains? Or is there another place to like better?
39~ What are your love languages?
8- What's your favorite flavor of ice cream? Do you a least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
What have you learned about yourself that you did not before this?
Prisoner/Prison Guard Landlord/Tenant
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
3- Should Pluto still be considered a planet? 4- How about smoking?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
1- What’s 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?
Does the thought excite you? Care to share?
32- What's your greatest talent? Can I see it right now?
60~ How important is oral sex? Do you like receiving? Do you like giving?
47~ What would be your dream job and why?
Would you do it again, and would you rather 2 females or 2 males?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
9~ How many times over your lifetime do you think you have had sex so far?
44~ Care to share something about yourself that no one else knows about you?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What would you say to prove to yourself that it was really you?
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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
38~ Share your most embarrassing sexual memory?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
36~ What is your favorite time of day to have sex/make love?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
53~ How much can you tell me about the one thing you are most passionate about?
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?
9- What’s your favorite season and why? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
If yes, what?
51~ What tends to bring a smile to your face?
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’s your favorite color? Do you a least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
70~ Would/do you have/like anal sex?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
(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…)
84~ How do you feel about reading/listening to adult stories?
19~ Who/when was your first “heartbreak”?
29- How superstitious are you?
5~ When you first started having sex, was it what you thought it would be?
13- What’s your favorite drink? What’s your least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
9- If you could have three wishes, what would they be? Why?
50~ How many children do you have? What are their ages?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Would you read them together?
What is your favorite toy? Ever wanted to try a specific toy?
7- What are your thoughts on religion? Is there an afterlife?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3- What Superhero or Superpower would you want to be/have?
14- What's your favorite dessert? Do you a least favorite?
7- What if a person smells a certain way? 8- How about smoking?
4- For a pet, Cat, dog or other?
10- What is your favorite family tradition? What’s your least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
31- If given a chance to be immortal, would you take it? Why?
How old are you? Male or Female?
11~ Have you ever been caught by your parents or children or others while having sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
19- What’s your favorite fairytale? What’s your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
12- What is the weirdest thing you've ever eaten?
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?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
3- What’s your favorite smell? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
34~ Do you like the lights on or off during sex?
Do you have a favorite? Is it ok if your partner does?
How well do you know me? And some of your thoughts about me
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
You know that I will be 100% truthful, so ask.
Doctor/Nurse Stripper/Client
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
13~ Is there a difference between, making love, having sex, and fucking?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
If NO, would you ever have one? Would it be with 2 men or 2 women?
Have you ever? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
11- List at least 5 things on your bucket list. Have you done any of them already?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
That one or two things that made you go hmmmm, OMG or wow!
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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?
* Give a rating for each one (0-100)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
48~ Have you ever paid or been paid for sex?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
42~ What’s your biggest regret in life?
26~ What side of the bed do you sleep on?
76~ Have you had a threesome? 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,
62~ Have you used adult toys?
Do you think this brought you closer together?
Any that are a turn off?
5- Have you ever been hypnotized? Would you allow yourself to be?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
92~ Everyone needs a “safe” word. What is yours?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
92~ Have you ever had or have an STD? How many? What was it?
20- What’s your favorite candy? What’s your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
Master/Slave Boss/Maid
22~ What is the best pickup line anyone has ever used on you? What was the worst?
8- What are your thoughts on politics?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
If you say it, I will stop, and we can talk about it when you are ready.
Model/Photographer Police/Criminal
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What is your favorite position? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
25~ How do you feel about PDA? (Public Display of Affection)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
29~ What are some things that turn you off? What is your biggest turn off?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
61~ How willing would you be to try new sexual positions?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
22- Do you have any birth marks? How about scars? Care to share how you got them?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
The Ice Breaker Questions
Do you watch it? What is your favorite?
*** Questions About Me ***
65~ Describe the best orgasm you’ve ever had? 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?
10- List 5 of your top pet peeves.
28~ What are some things that turn on? What is your biggest turn on?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Any that are a turn off?
How many partners have you had oral sex with? Who? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Repairman/Lonely Wife Virgin/Experienced
46~ Have you ever used furniture, or other types of things to aid you while having sex?
15~ Have you ever been “in love”? Who? Care to Share?
23- What is your dream job? What was it as a child?
30~ What's something unexpected that turns you on?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Nothing too Serious
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…
52~ What are your hobbies?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
Would /have you ever given your partner a lap dance and Striptease?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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…
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
40~ What’s the weirdest place you’ve ever had sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
83~ How do you feel about Porn?
27- What was/ is nickname? Does it have a meaning behind it?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
If you win, what will you make them do?
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)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?