What is the most interesting question you can ask to get to know someone?
13.06.2025 03:23
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
53~ How much can you tell me about the one thing you are most passionate about?
What 10 things have you stopped doing in your life?
56~ Would you ever go to a strip club 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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Has your wife made you a cuckold?
*** Random Questions ***
51~ Are you willing to play adult games with your partner?
Would you read them together?
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(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…)
71~ Would you give your partner a hand or foot job? Would you receive one?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Why am I so afraid that gun owners have set traps to kill me outside my house or my car?
Would you allow me to clean every part of your body with my soapy hands and fingers?
29- How superstitious are you?
The Ice Breaker Questions
How old are you? Male or Female?
28~ What are some things that turn on? What is your biggest turn on?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Why did my ex-narcissist move so fast with his new supply marriage engagement moving in, etc.?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Over time has your thoughts on sex changed?
Why do I feel like something bad is going to happen to me?
36~ What is your favorite time of day to have sex/make love?
26~ What side of the bed do you sleep on?
51~ What tends to bring a smile to your face?
How do you write a letter to your uncle who sent you money for your birthday outfit?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
7- What are your thoughts on religion? Is there an afterlife?
52~ What are your hobbies?
Rory McIlroy addresses driver situation and the 81 he shot in practice at Oakmont - NBC Sports
31- If given a chance to be immortal, would you take it? Why?
15~ Have you ever been “in love”? Who? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Nurse/Patient Celebrity/Fan
Why do so many guys love anime girls?
6- Do you have dreams? Can you remember them? What do you usually dream about?
What is your favorite toy? Ever wanted to try a specific toy?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What story do you have involving a public restroom?
11~ Have you ever been caught by your parents or children or others while having sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral 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.
Supernovae may have kicked off abrupt climate shifts in the past—and they could again - Phys.org
Model/Photographer Police/Criminal
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Any that are a turn off?
What is the best way to keep my vagina clean and fresh?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
If you win, what will you make them do?
10- What is your favorite family tradition? What’s your least favorite?
82~ Do you have any fantasies involving Role-Playing?
20- What’s your favorite candy? What’s your least favorite?
42~ What’s your biggest regret in life?
48~ Have you ever paid or been paid for sex?
Have you ever? Care to Share?
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Do you watch it? What is your favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
65~ Describe the best orgasm you’ve ever had? Care to share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
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?
39~ What are your love languages?
That one or two things that made you go hmmmm, OMG or wow!
Do you like it when they show and tell you what they want?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
25~ How do you feel about PDA? (Public Display of Affection)
92~ Everyone needs a “safe” word. What is yours?
If YES, was it with 2 men or 2 women? Did you enjoy it?
*** Deal Breaker Questions ***
How many times do you think you have “made love”?
22- What is your favorite childhood memory? What is your least favorite?
19- Do/have you smoked? What do you prefer? How often?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Does the thought excite you? Care to share?
Do you have a favorite? Is it ok if your partner does?
49~ How many times have you been married? Why did they end?
36- Do you play video games? What is your favorite? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
27- What was/ is nickname? Does it have a meaning behind it?
3- What’s your favorite smell? Do you a least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
81~ Do you have any kinks and/or fetishes?
Escort/Client Job Applicant/Hiring Manager
If NO, would you ever have one? Would it be with 2 men or 2 women?
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?
If yes, what?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
40~ What’s the weirdest place you’ve ever had sex?
32- What's your greatest talent? Can I see it right now?
17- What’s your favorite holiday? What’s your least favorite?
47~ What would be your dream job and why?
84~ How do you feel about reading/listening to adult stories?
18~ Who/when was your first “crush”?
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?
14- What's your favorite dessert? Do you a least favorite?
7- What if a person smells a certain way? 8- How about smoking?
Repairman/Lonely Wife Virgin/Experienced
92~ Have you ever had or have an STD? How many? What was it?
How many partners have you had oral sex with? Who? Care to Share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Do you like the “69” position? Do you prefer to be on top or bottom?
33- If you could visit any time period, when would you pick? Please explain why?
*** Questions about Relationships/Past ***
11- What's your favorite restaurant? 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)?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
9- If you could have three wishes, what would they be? Why?
70~ Would/do you have/like anal sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
89~ Do you like taking showers together?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Teacher/Student Stranger/One Night Stand
You know that I will be 100% truthful, so ask.
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
49~ If you could, would you want to be the opposite sex for a day, week, or year?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Would you mind if your partner watched it? How about together vs alone?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Family Relation Age Play
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,
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
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)
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
1- What’s your favorite animal? Do you a least favorite?
Would /have you ever given your partner a lap dance and Striptease?
What would you say to prove to yourself that it was really you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
21~ What was the best date you ever went on? What has been the worst?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
7-What do I do in bed that drives you wild? How about, what turns you off?
10- List 5 of your top pet peeves.
83~ How do you feel about Porn?
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?
Can you Deep Throat? Do you like the taste of yourself?
15- What bad habit do you wish you could quit? Do you have any addictions?
33- Beach or Mountains? Or is there another place to like better?
37- Do you like your name? If you could change it, what would you change it too?
9- What’s your favorite season and why? What’s your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
60~ How important is oral sex? Do you like receiving? Do you like giving?
1- What was your first impression of me? Has it changed?
17- Have you ever done drugs? Which ones? How often?
1~ How old were you when you had your first kiss? 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?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
I would allow you to do it… What would you do to me?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
8- What are your thoughts on politics?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
4- For a pet, Cat, dog or other?
67~ Do you like it when your partner moans and/or is vocal during sex?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Prisoner/Prison Guard Landlord/Tenant
Master/Slave Boss/Maid
If you say it, I will stop, and we can talk about it when you are ready.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
What is your view on sex? Meaning, When/Where/ How often/
Would you do it again, and would you rather 2 females or 2 males?
Get this wrong and this could mean the end… :-) some funny, some not…
48~ Do you have any siblings? Are you close to your family?
61~ How willing would you be to try new sexual positions?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
5~ When you first started having sex, was it what you thought it would be?
19~ Who/when was your first “heartbreak”?
12- What’s your favorite food? What’s your least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
13~ Is there a difference between, making love, having sex, and fucking?
13- How about having a certain hair cut/style?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Do you think this brought you closer together?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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…
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
76~ Have you had a threesome? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
64~ When was your very first orgasm? When was your first from having sex? Care to share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
What have you learned about me that was new and/or surprising?
29~ What are some things that turn you off? What is your biggest turn off?
How well do you know me? And some of your thoughts about me
3- What Superhero or Superpower would you want to be/have?
44~ Care to share something about yourself that no one else knows about you?
What was the longest? What was the shortest?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
2- What’s your favorite color? Do you a least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
12- What is the weirdest thing you've ever eaten?
22- Do you have any birth marks? How about scars? Care to share how you got them?
38~ Share your most embarrassing sexual memory?
34- Ever been to a concert? What was your favorite? Who would you like to see?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
45~ How do you feel about me blindfolding you? How about blindfolding me?
18- How often do you drink alcohol? What is your favorite drink?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
*** What’s Your Favorite…? ***
30~ What's something unexpected that turns you on?
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?
11- How about if they like a certain sports team? 12-How about drinking too much?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Please share Did you stop?
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?
13- What’s your favorite drink? What’s your least favorite?
*** Questions About Me ***
How about if they talk dirty and/or call you names?
3- Should Pluto still be considered a planet? 4- How about smoking?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
34~ Do you like the lights on or off during sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
* Give a rating for each one (0-100)
13- What is the craziest/scariest thing you've ever done?
23- What is your dream job? What was it as a child?
50~ How many children do you have? What are their ages?
What do you dislike about me? I asked you to be 100% honest.
9- Is there something you’ve always wanted to ask me but you’re afraid?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
28- What are some things that people do that irritate you?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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…
Any that are a turn off?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
15- What's your favorite saying? What word or phrase is your least favorite?
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?
Nothing too Serious
19- What’s your favorite fairytale? What’s your least favorite?
Doctor/Nurse Stripper/Client
21- What's your favorite way to spend a weekend or time off?
What have you learned about yourself that you did not before this?
52~ Are you willing to make “those types” of bets with your partner?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
What is your favorite position? Why?
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?
62~ Have you used adult toys?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?