What is the most interesting question you can ask to get to know someone?
Last Updated: 25.06.2025 00:21
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,
11~ Have you ever been caught by your parents or children or others while having sex?
Nothing too Serious
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5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How many partners have you had oral sex with? Who? Care to Share?
Would you mind if your partner watched it? How about together vs alone?
What is your favourite summer outfit? Why?
92~ Everyone needs a “safe” word. What is yours?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
61~ How willing would you be to try new sexual positions?
How do I explain to my husband that my 19-year-old son has accidentally gotten me pregnant?
22- Do you have any birth marks? How about scars? Care to share how you got them?
9- If you could have three wishes, what would they be? Why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
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* Which of the following turns you on the most? Do you have any not on this list? Care to share?
8- What are your thoughts on politics?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Does the thought excite you? Care to share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
9- What’s your favorite season and why? What’s your least favorite?
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65~ Describe the best orgasm you’ve ever had? Care to share?
50~ How many children do you have? What are their ages?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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5~ When you first started having sex, was it what you thought it would be?
47~ What would be your dream job and why?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How do I study with focus and concentration and avoid distractions and procrastination?
10- What is your favorite family tradition? What’s your least favorite?
Family Relation Age Play
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Is it true that schizophrenia can sometimes be a demonic attack or black magic?
Doctor/Nurse Stripper/Client
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…
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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What is your view on sex? Meaning, When/Where/ How often/
*** Random Questions ***
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Get this wrong and this could mean the end… :-) some funny, some not…
Do you have a favorite? Is it ok if your partner does?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
19~ Who/when was your first “heartbreak”?
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9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Please share Did you stop?
* Give a rating for each one (0-100)
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
71~ Would you give your partner a hand or foot job? Would you receive one?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
13- How about having a certain hair cut/style?
2- What’s your favorite color? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
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…
49~ How many times have you been married? Why did they end?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
32- What's your greatest talent? Can I see it right now?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
*** Deal Breaker Questions ***
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?
How old are you? Male or Female?
51~ Are you willing to play adult games with your partner?
*** Questions About Me ***
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
1~ How old were you when you had your first kiss? Who? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
19- What’s your favorite fairytale? What’s your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
70~ Would/do you have/like anal sex?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
5- Have you ever been hypnotized? Would you allow yourself to be?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
36~ What is your favorite time of day to have sex/make love?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
4- For a pet, Cat, dog or other?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Would you do it again, and would you rather 2 females or 2 males?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If yes, what?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
What would you say to prove to yourself that it was really you?
Can you Deep Throat? Do you like the taste of yourself?
14- What's your favorite dessert? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
(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…)
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
62~ Have you used adult toys?
What is your favorite position? Why?
13- What is the craziest/scariest thing you've ever done?
76~ Have you had a threesome? Care to Share?
Do you think this brought you closer together?
Do you watch it? What is your favorite?
What have you learned about me that was new and/or surprising?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
That one or two things that made you go hmmmm, OMG or wow!
28- What are some things that people do that irritate you?
You know that I will be 100% truthful, so ask.
10~ How many dates are necessary before you to have sex with someone?
3- What’s your favorite smell? Do you a least favorite?
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
33- If you could visit any time period, when would you pick? Please explain why?
34~ Do you like the lights on or off during sex?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
10- List 5 of your top pet peeves.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
28~ What are some things that turn on? What is your biggest turn on?
Over time has your thoughts on sex changed?
40~ What’s the weirdest place you’ve ever had sex?
What do you dislike about me? I asked you to be 100% honest.
27- What was/ is nickname? Does it have a meaning behind it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
81~ Do you have any kinks and/or fetishes?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
22- What is your favorite childhood memory? What is your least favorite?
Repairman/Lonely Wife Virgin/Experienced
Nurse/Patient Celebrity/Fan
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Would you ever want to be woken up with oral and/or intercourse?
7- What if a person smells a certain way? 8- How about smoking?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
If you say it, I will stop, and we can talk about it when you are ready.
31- If given a chance to be immortal, would you take it? Why?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Will you cheat again? How can, you be sure? Define what cheating is to you.
3- Should Pluto still be considered a planet? 4- How about smoking?
29~ What are some things that turn you off? What is your biggest turn off?
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?
83~ How do you feel about Porn?
44~ Care to share something about yourself that no one else knows about 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?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
If NO, would you ever have one? Would it be with 2 men or 2 women?
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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
26~ What side of the bed do you sleep on?
1- What was your first impression of me? Has it changed?
7- What are your thoughts on religion? Is there an afterlife?
Teacher/Student Stranger/One Night Stand
21- What's your favorite way to spend a weekend or time off?
60~ How important is oral sex? Do you like receiving? Do you like giving?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
17- What’s your favorite holiday? What’s your least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
33- Beach or Mountains? Or is there another place to like better?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
21~ What was the best date you ever went on? What has been the worst?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
If YES, was it with 2 men or 2 women? Did you enjoy it?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
52~ Are you willing to make “those types” of bets with your partner?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
42~ What’s your biggest regret in life?
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?
How many times do you think you have “made love”?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Any that are a turn off?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
1- What’s your favorite animal? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Do you like the “69” position? Do you prefer to be on top or bottom?
20- What’s your favorite candy? What’s your least favorite?
The Ice Breaker Questions
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Would you read them together?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
80~ Share your top three fantasies/desires. (Be detailed) 😊
17- Have you ever done drugs? Which ones? How often?
29- How superstitious are you?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Model/Photographer Police/Criminal
84~ How do you feel about reading/listening to adult stories?
Master/Slave Boss/Maid
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?
How well do you know me? And some of your thoughts about me
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What have you learned about yourself that you did not before this?
52~ What are your hobbies?
*** What’s Your Favorite…? ***
53~ How much can you tell me about the one thing you are most passionate about?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
51~ What tends to bring a smile to your face?
Would /have you ever given your partner a lap dance and Striptease?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
48~ Do you have any siblings? Are you close to your family?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
25~ How do you feel about PDA? (Public Display of Affection)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Escort/Client Job Applicant/Hiring Manager
18~ Who/when was your first “crush”?
36- Do you play video games? What is your favorite? Do you a least favorite?
13- What’s your favorite drink? What’s your least favorite?
12- What is the weirdest thing you've ever eaten?
11- What's your favorite restaurant? What’s your least favorite?
48~ Have you ever paid or been paid for sex?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
92~ Have you ever had or have an STD? How many? What was it?
3- What Superhero or Superpower would you want to be/have?
Any that are a turn off?
7-What do I do in bed that drives you wild? How about, what turns you off?
67~ Do you like it when your partner moans and/or is vocal during sex?
Have you ever? Care to Share?
Do you like it when they show and tell you what they want?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
13~ Is there a difference between, making love, having sex, and fucking?
*** Questions about Relationships/Past ***
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
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)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
18- How often do you drink alcohol? What is your favorite drink?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
37- Do you like your name? If you could change it, what would you change it too?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
39~ What are your love languages?
15- What bad habit do you wish you could quit? Do you have any addictions?
89~ Do you like taking showers together?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
30~ What's something unexpected that turns you on?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
How about if they talk dirty and/or call you names?
15- What's your favorite saying? What word or phrase is your least favorite?
If you win, what will you make them do?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
I would allow you to do it… What would you do to me?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
12- What’s your favorite food? What’s your least favorite?
What was the longest? What was the shortest?
Prisoner/Prison Guard Landlord/Tenant
19- Do/have you smoked? What do you prefer? How often?