What is the most interesting question you can ask to get to know someone?
09.06.2025 02:19
Do you like the “69” position? Do you prefer to be on top or bottom?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
47~ What would be your dream job and why?
What do you do when you are struggling to fall asleep?
11- What's your favorite restaurant? What’s your least favorite?
81~ Do you have any kinks and/or fetishes?
Will you cheat again? How can, you be sure? Define what cheating is to you.
R.I.P Loretta Swit: How well do you remember ''Hot Lips'' Houlihan? - MeTV
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Would you do it again, and would you rather 2 females or 2 males?
11- How about if they like a certain sports team? 12-How about drinking too much?
How much should one budget to travel for 1 month generally?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
* Give a rating for each one (0-100)
If YES, was it with 2 men or 2 women? Did you enjoy it?
Have you ever been instructed/forced to crossdress for the benefit of others?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Would you mind if your partner watched it? How about together vs alone?
38~ Share your most embarrassing sexual memory?
UK has fingers in its ears over Trump’s defense threat - politico.eu
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? 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 about if they talk dirty and/or call you names?
33- Beach or Mountains? Or is there another place to like better?
If you say it, I will stop, and we can talk about it when you are ready.
Nothing too Serious
How Can AI Researchers Save Energy? By Going Backward. - Quanta Magazine
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
How do women feel when they are in love?
9- If you could have three wishes, what would they be? Why?
What have you learned about me that was new and/or surprising?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Google’s Pixel 10 phones will reportedly launch on August 13th - The Verge
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
19- Do/have you smoked? What do you prefer? How often?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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,
Prisoner/Prison Guard Landlord/Tenant
36- Do you play video games? What is your favorite? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
41~ Are there moments in your past that you would want to change? Please share 3 of them.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
49~ How many times have you been married? Why did they end?
11~ Have you ever been caught by your parents or children or others while having sex?
4- For a pet, Cat, dog or other?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
5~ When you first started having sex, was it what you thought it would be?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
15~ Have you ever been “in love”? Who? Care to Share?
10- List 5 of your top pet peeves.
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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?
51~ What tends to bring a smile to your face?
What is your view on sex? Meaning, When/Where/ How often/
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Family Relation Age Play
20- What’s your favorite candy? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
23- What is your dream job? What was it as a child?
42~ What’s your biggest regret in life?
Any that are a turn off?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
61~ How willing would you be to try new sexual positions?
67~ Do you like it when your partner moans and/or is vocal during sex?
2- What’s your favorite color? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
30~ What's something unexpected that turns you on?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Master/Slave Boss/Maid
15- What's your favorite saying? What word or phrase is your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
9- Is there something you’ve always wanted to ask me but you’re afraid?
21~ What was the best date you ever went on? What has been the worst?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Do you think this brought you closer together?
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?
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…
Get this wrong and this could mean the end… :-) some funny, some not…
82~ Do you have any fantasies involving Role-Playing?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Nurse/Patient Celebrity/Fan
25~ How do you feel about PDA? (Public Display of Affection)
27- What was/ is nickname? Does it have a meaning behind it?
19~ Who/when was your first “heartbreak”?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
13- What is the craziest/scariest thing you've ever done?
22- Do you have any birth marks? How about scars? Care to share how you got them?
7- What if a person smells a certain way? 8- How about smoking?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
68~ Would you ever get your partner up from bed by using oral sex 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?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
52~ What are your hobbies?
32- What's your greatest talent? Can I see it right now?
*** Deal Breaker Questions ***
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
1- What was your first impression of me? Has it changed?
26~ What side of the bed do you sleep on?
29~ What are some things that turn you off? What is your biggest turn off?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What was the longest? What was the shortest?
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?
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?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
8- What are your thoughts on politics?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
44~ Care to share something about yourself that no one else knows about you?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What do you dislike about me? I asked you to be 100% honest.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
62~ Have you used adult toys?
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?
(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…)
3- What Superhero or Superpower would you want to be/have?
10~ How many dates are necessary before you to have sex with someone?
Any that are a turn off?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
39~ What are your love languages?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
That one or two things that made you go hmmmm, OMG or wow!
5- Have you ever been hypnotized? Would you allow yourself to be?
Can you Deep Throat? Do you like the taste of yourself?
How old are you? Male or Female?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Over time has your thoughts on sex changed?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Escort/Client Job Applicant/Hiring Manager
What is your favorite position? Why?
How many times do you think you have “made love”?
12- What is the weirdest thing you've ever eaten?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
18~ Who/when was your first “crush”?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
84~ How do you feel about reading/listening to adult stories?
21- What's your favorite way to spend a weekend or time off?
17- Have you ever done drugs? Which ones? How often?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Have you ever? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
13- How about having a certain hair cut/style?
Would you allow me to clean every part of your body with my soapy hands and fingers?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
34~ Do you like the lights on or off during sex?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
6- Do you have dreams? Can you remember them? What do you usually dream about?
14- What's your favorite dessert? Do you a least favorite?
What would you say to prove to yourself that it was really you?
The Ice Breaker Questions
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
1~ How old were you when you had your first kiss? Who? Care to Share?
If yes, what?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Would you read them together?
How many partners have you had oral sex with? Who? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
14- What is an embarrassing moment in your life? How about your most embarrassing?
51~ Are you willing to play adult games with your partner?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
28- What are some things that people do that irritate you?
13- What’s your favorite drink? What’s your least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
71~ Would you give your partner a hand or foot job? Would you receive one?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What is your favorite toy? Ever wanted to try a specific toy?
83~ How do you feel about Porn?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
37- Do you like your name? If you could change it, what would you change it too?
18- How often do you drink alcohol? What is your favorite drink?
3- What’s your favorite smell? Do you a least favorite?
I would allow you to do it… What would you do to me?
Teacher/Student Stranger/One Night Stand
Would you ever want to be woken up with oral and/or intercourse?
76~ Have you had a threesome? Care to Share?
What have you learned about yourself that you did not before this?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
89~ Do you like taking showers together?
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…
9~ How many times over your lifetime do you think you have had sex so far?
*** Random Questions ***
8- What's your favorite flavor of ice cream? Do you a least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you like it when they show and tell you what they want?
65~ Describe the best orgasm you’ve ever had? Care to share?
Model/Photographer Police/Criminal
46~ Have you ever used furniture, or other types of things to aid you while having sex?
*** Questions About Me ***
9- What’s your favorite season and why? What’s your least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
19- What’s your favorite fairytale? What’s your least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
Please share Did you stop?
50~ How many children do you have? What are their ages?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Do you have a favorite? Is it ok if your partner does?
22- What is your favorite childhood memory? What is your least favorite?
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?
10- What is your favorite family tradition? What’s your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
*** What’s Your Favorite…? ***
Does the thought excite you? Care to share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
3- Should Pluto still be considered a planet? 4- How about smoking?
53~ How much can you tell me about the one thing you are most passionate about?
48~ Have you ever paid or been paid for sex?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
If NO, would you ever have one? Would it be with 2 men or 2 women?
7- What are your thoughts on religion? Is there an afterlife?
36~ What is your favorite time of day to have sex/make love?
You know that I will be 100% truthful, so ask.
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
12- What’s your favorite food? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
48~ Do you have any siblings? Are you close to your family?
15- What bad habit do you wish you could quit? Do you have any addictions?
*** Questions about Relationships/Past ***
Do you watch it? What is your favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
92~ Have you ever had or have an STD? How many? What was it?
1- What’s your favorite animal? Do you a least favorite?
29- How superstitious are you?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
28~ What are some things that turn on? What is your biggest turn on?
If you win, what will you make them do?
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
52~ Are you willing to make “those types” of bets with your partner?
Doctor/Nurse Stripper/Client
70~ Would/do you have/like anal sex?
31- If given a chance to be immortal, would you take it? Why?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
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?