What is the most interesting question you can ask to get to know someone?
Last Updated: 16.06.2025 07:18
Will you cheat again? How can, you be sure? Define what cheating is to you.
*** Questions about Relationships/Past ***
13- How about having a certain hair cut/style?
Are women as visual as men are?
What is your favorite toy? Ever wanted to try a specific toy?
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…
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Doctor/Nurse Stripper/Client
14- What's your favorite dessert? Do you a least favorite?
I just cannot wake up early, even if I sleep on time. What should I do?
23- What is your dream job? What was it as a child?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
8- What's your favorite flavor of ice cream? Do you a least favorite?
Opinion: The secret to a longer life could be this old-fashioned English breakfast - MarketWatch
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
26~ What side of the bed do you sleep on?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Would /have you ever given your partner a lap dance and Striptease?
How well do you know me? And some of your thoughts about me
In what ways does Islam oppress women?
92~ Have you ever had or have an STD? How many? What was it?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
9~ How many times over your lifetime do you think you have had sex so far?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
3- What’s your favorite smell? Do you a least favorite?
What was your best unexpected reunion with your childhood best friend?
5~ When you first started having sex, was it what you thought it would be?
What do you dislike about me? I asked you to be 100% honest.
Can you Deep Throat? Do you like the taste of yourself?
Why is my ex trying to provoke an argument with me?
28~ What are some things that turn on? What is your biggest turn on?
Would you mind if your partner watched it? How about together vs alone?
51~ Are you willing to play adult games with your partner?
Why does everyone hate Ed Sheeran so much?
33- If you could visit any time period, when would you pick? Please explain why?
What was the longest? What was the shortest?
19- Do/have you smoked? What do you prefer? How often?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
11- What's your favorite restaurant? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
What are some mind-blowing facts about Michael Jackson?
17- What’s your favorite holiday? What’s your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
1- What’s your favorite animal? Do you a least favorite?
Can a Trump supporter explain what was wrong with what Bishop Budde said to Donald Trump?
You know that I will be 100% truthful, so ask.
If yes, what?
How old are you? Male or Female?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
62~ Have you used adult toys?
If you say it, I will stop, and we can talk about it when you are ready.
49~ How many times have you been married? Why did they end?
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,
65~ Describe the best orgasm you’ve ever had? 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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you do it again, and would you rather 2 females or 2 males?
48~ Do you have any siblings? Are you close to your family?
13- What’s your favorite drink? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
Get this wrong and this could mean the end… :-) some funny, some not…
If NO, would you ever have one? Would it be with 2 men or 2 women?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
Family Relation Age Play
48~ Have you ever paid or been paid for sex?
Would you read them together?
31- If given a chance to be immortal, would you take it? Why?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
13- What is the craziest/scariest thing you've ever done?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
6- Do you have dreams? Can you remember them? What do you usually dream about?
39~ What are your love languages?
What is your view on sex? Meaning, When/Where/ How often/
What is your favorite position? Why?
9- What’s your favorite season and why? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
1~ How old were you when you had your first kiss? Who? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
19~ Who/when was your first “heartbreak”?
28- What are some things that people do that irritate you?
76~ Have you had a threesome? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
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?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
40~ What’s the weirdest place you’ve ever had sex?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
50~ How many children do you have? What are their ages?
34~ Do you like the lights on or off during sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Escort/Client Job Applicant/Hiring Manager
83~ How do you feel about Porn?
What have you learned about yourself that you did not before this?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
47~ What would be your dream job and why?
52~ What are your hobbies?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Does the thought excite you? Care to share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
61~ How willing would you be to try new sexual positions?
What have you learned about me that was new and/or surprising?
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?
*** Questions About Me ***
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
42~ What’s your biggest regret in life?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
Do you like the “69” position? Do you prefer to be on top or bottom?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Nurse/Patient Celebrity/Fan
41~ Are there moments in your past that you would want to change? Please share 3 of them.
11~ Have you ever been caught by your parents or children or others while having sex?
Any that are a turn off?
15- What bad habit do you wish you could quit? Do you have any addictions?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7- What are your thoughts on religion? Is there an afterlife?
1- What was your first impression of me? Has it changed?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
45~ How do you feel about me blindfolding you? How about blindfolding me?
20- What’s your favorite candy? What’s your least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
84~ How do you feel about reading/listening to adult stories?
Model/Photographer Police/Criminal
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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…
12- What’s your favorite food? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
10- List 5 of your top pet peeves.
If YES, was it with 2 men or 2 women? Did you enjoy it?
*** Deal Breaker Questions ***
22- Do you have any birth marks? How about scars? Care to share how you got them?
Do you watch it? What is your favorite?
Any that are a turn off?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
11- How about if they like a certain sports team? 12-How about drinking too much?
Teacher/Student Stranger/One Night Stand
I would allow you to do it… What would you do to me?
*** Random Questions ***
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Have you ever? Care to Share?
2- What’s your favorite color? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
18- How often do you drink alcohol? What is your favorite drink?
36- Do you play video games? What is your favorite? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you ever want to be woken up with oral and/or intercourse?
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?
44~ Care to share something about yourself that no one else knows about you?
70~ Would/do you have/like anal sex?
10~ How many dates are necessary before you to have sex with someone?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
18- What’s your favorite way to relax after a long day? What’s your least favorite?
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)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
8- What are your thoughts on politics?
7-What do I do in bed that drives you wild? How about, what turns you off?
11- List at least 5 things on your bucket list. Have you done any of them already?
Nothing too Serious
Master/Slave Boss/Maid
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
51~ What tends to bring a smile to your face?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Do you like it when they show and tell you what they want?
Do you have a favorite? Is it ok if your partner does?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
If you win, what will you make them do?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
How many times do you think you have “made love”?
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?
That one or two things that made you go hmmmm, OMG or wow!
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
The Ice Breaker Questions
19- What’s your favorite fairytale? What’s your least favorite?
How about if they talk dirty and/or call you names?
15~ Have you ever been “in love”? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
82~ Do you have any fantasies involving Role-Playing?
52~ Are you willing to make “those types” of bets with your partner?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
22- What is your favorite childhood memory? What is your least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
17- Have you ever done drugs? Which ones? How often?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
How many partners have you had oral sex with? Who? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
27- What was/ is nickname? Does it have a meaning behind it?
4- For a pet, Cat, dog or other?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
29- How superstitious are you?
10- What is your favorite family tradition? What’s your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
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?
32- What's your greatest talent? Can I see it right now?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
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)
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
(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…)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Prisoner/Prison Guard Landlord/Tenant
3- Should Pluto still be considered a planet? 4- How about smoking?
92~ Everyone needs a “safe” word. What is yours?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
81~ Do you have any kinks and/or fetishes?
36~ What is your favorite time of day to have sex/make love?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Please share Did you stop?
12- What is the weirdest thing you've ever eaten?
Repairman/Lonely Wife Virgin/Experienced
49~ If you could, would you want to be the opposite sex for a day, week, or year?
89~ Do you like taking showers together?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
9- If you could have three wishes, what would they be? Why?
21~ What was the best date you ever went on? What has been the worst?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
29~ What are some things that turn you off? What is your biggest turn off?
3- What Superhero or Superpower would you want to be/have?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What would you say to prove to yourself that it was really you?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
38~ Share your most embarrassing sexual memory?
14- What is an embarrassing moment in your life? How about your most embarrassing?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
30~ What's something unexpected that turns you on?
18~ Who/when was your first “crush”?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
*** What’s Your Favorite…? ***
33- Beach or Mountains? Or is there another place to like better?
25~ How do you feel about PDA? (Public Display of Affection)
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?
67~ Do you like it when your partner moans and/or is vocal during sex?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Over time has your thoughts on sex changed?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.