What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 04:35
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Would /have you ever given your partner a lap dance and Striptease?
17- Have you ever done drugs? Which ones? How often?
Dakota Johnson Raves About Working With First Intimacy Coordinator: “It’s Not Sexy” - Deadline
Nurse/Patient Celebrity/Fan
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
33- If you could visit any time period, when would you pick? Please explain why?
What does the Bible say about the Antichrist? How will we know when he arrives on the scene?
The Ice Breaker Questions
*** Questions about Relationships/Past ***
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
If Trump were to lose in 2024, would that be the end of his grip on the Republican Party?
48~ Have you ever paid or been paid for sex?
How well do you know me? And some of your thoughts about me
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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5~ When you first started having sex, was it what you thought it would be?
5- Have you ever been hypnotized? Would you allow yourself to be?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What factors contributed to The Beatles' bitterness?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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)
What does it mean when we dream about demons, ghosts, monsters, etc.?
13- What’s your favorite drink? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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30~ What's something unexpected that turns you on?
50~ How many children do you have? What are their ages?
How many times do you think you have “made love”?
Should transgender Ideology be renamed "Gender Revisionism/Biological Denialism"?
18~ Who/when was your first “crush”?
51~ Are you willing to play adult games with your partner?
34~ Do you like the lights on or off during sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
84~ How do you feel about reading/listening to adult stories?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
How can I remove decimals in math?
65~ Describe the best orgasm you’ve ever had? Care to share?
*** Questions About Me ***
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What is the meaning of "ero" in Japanese?
Does the thought excite you? Care to share?
92~ Have you ever had or have an STD? How many? What was it?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
How do you weigh in on the Vance-couch conversation?
If yes, what?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
That one or two things that made you go hmmmm, OMG or wow!
Have you had any paranormal activity situations happen personally to you or someone you know?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
If NO, would you ever have one? Would it be with 2 men or 2 women?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
What would you say to prove to yourself that it was really you?
10~ How many dates are necessary before you to have sex with someone?
21~ What was the best date you ever went on? What has been the worst?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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?
You know that I will be 100% truthful, so ask.
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Would you allow me to clean every part of your body with my soapy hands and fingers?
What is your favorite position? Why?
18- How often do you drink alcohol? What is your favorite drink?
76~ Have you had a threesome? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
If you say it, I will stop, and we can talk about it when you are ready.
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
I would allow you to do it… What would you do to me?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
1- What’s your favorite animal? Do you a least favorite?
51~ What tends to bring a smile to your face?
52~ Are you willing to make “those types” of bets with your partner?
28~ What are some things that turn on? What is your biggest turn on?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
19- Do/have you smoked? What do you prefer? How often?
Repairman/Lonely Wife Virgin/Experienced
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
71~ Would you give your partner a hand or foot job? Would you receive one?
38~ Share your most embarrassing sexual memory?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
7- What are your thoughts on religion? Is there an afterlife?
* Give a rating for each one (0-100)
52~ What are your hobbies?
Any that are a turn off?
Do you watch it? What is your favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
10- What is your favorite family tradition? What’s your least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Do you like the “69” position? Do you prefer to be on top or bottom?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Prisoner/Prison Guard Landlord/Tenant
27- What was/ is nickname? Does it have a meaning behind it?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If YES, was it with 2 men or 2 women? Did you enjoy it?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
If you win, what will you make them do?
60~ How important is oral sex? Do you like receiving? Do you like giving?
3- What’s your favorite smell? Do you a least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
39~ What are your love languages?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
How old are you? Male or Female?
What have you learned about yourself that you did not before this?
14- What's your favorite dessert? Do you a least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
21- What's your favorite way to spend a weekend or time off?
70~ Would/do you have/like anal sex?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Please share Did you stop?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
12- What’s your favorite food? What’s your least favorite?
11- What's your favorite restaurant? What’s your least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
36~ What is your favorite time of day to have sex/make love?
Any that are a turn off?
20- What’s your favorite candy? What’s your least favorite?
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
9- If you could have three wishes, what would they be? Why?
Nothing too Serious
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?
10- List 5 of your top pet peeves.
11- How about if they like a certain sports team? 12-How about drinking too much?
92~ Everyone needs a “safe” word. What is yours?
Doctor/Nurse Stripper/Client
Do you think this brought you closer together?
*** Random Questions ***
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
28- What are some things that people do that irritate you?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
8- What are your thoughts on politics?
7- What if a person smells a certain way? 8- How about smoking?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
1~ How old were you when you had your first kiss? Who? Care to Share?
61~ How willing would you be to try new sexual positions?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How about if they talk dirty and/or call you names?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
9- Is there something you’ve always wanted to ask me but you’re afraid?
(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…)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Family Relation Age Play
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
23- What is your dream job? What was it as a child?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
3- What Superhero or Superpower would you want to be/have?
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?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
40~ What’s the weirdest place you’ve ever had sex?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Escort/Client Job Applicant/Hiring Manager
15- What's your favorite saying? What word or phrase is your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
36- Do you play video games? What is your favorite? Do you a least favorite?
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…
26~ What side of the bed do you sleep on?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What is your favorite toy? Ever wanted to try a specific toy?
34- Ever been to a concert? What was your favorite? Who would you like to see?
19- What’s your favorite fairytale? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
48~ Do you have any siblings? Are you close to your family?
What is your view on sex? Meaning, When/Where/ How often/
3- Should Pluto still be considered a planet? 4- How about smoking?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
19~ Who/when was your first “heartbreak”?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
2- What’s your favorite color? Do you a least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Would you mind if your partner watched it? How about together vs alone?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
15~ Have you ever been “in love”? Who? 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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
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…
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,
83~ How do you feel about Porn?
Master/Slave Boss/Maid
62~ Have you used adult toys?
13~ Is there a difference between, making love, having sex, and fucking?
Get this wrong and this could mean the end… :-) some funny, some not…
What do you dislike about me? I asked you to be 100% honest.
13- What is the craziest/scariest thing you've ever done?
9- What’s your favorite season and why? What’s your least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
13- How about having a certain hair cut/style?
Would you do it again, and would you rather 2 females or 2 males?
33- Beach or Mountains? Or is there another place to like better?
44~ Care to share something about yourself that no one else knows about you?
Over time has your thoughts on sex changed?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
9~ How many times over your lifetime do you think you have had sex so far?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What was the longest? What was the shortest?
12- What is the weirdest thing you've ever eaten?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
47~ What would be your dream job and why?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
29~ What are some things that turn you off? What is your biggest turn off?
31- If given a chance to be immortal, would you take it? Why?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
32- What's your greatest talent? Can I see it right now?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) 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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
22- Do you have any birth marks? How about scars? Care to share how you got them?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
67~ Do you like it when your partner moans and/or is vocal during sex?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
What have you learned about me that was new and/or surprising?
89~ Do you like taking showers together?
81~ Do you have any kinks and/or fetishes?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Teacher/Student Stranger/One Night Stand
22- What is your favorite childhood memory? What is your least favorite?
*** What’s Your Favorite…? ***
11- List at least 5 things on your bucket list. Have you done any of them already?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
82~ Do you have any fantasies involving Role-Playing?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
15- What bad habit do you wish you could quit? Do you have any addictions?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
1- What was your first impression of me? Has it changed?
29- How superstitious are you?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Would you read them together?
17- What’s your favorite holiday? What’s your least favorite?
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?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
37- Do you like your name? If you could change it, what would you change it too?
42~ What’s your biggest regret in life?
49~ How many times have you been married? Why did they end?
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?
Model/Photographer Police/Criminal
4- For a pet, Cat, dog or other?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
*** Deal Breaker Questions ***
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
How many partners have you had oral sex with? Who? Care to Share?
Have you ever? Care to Share?