What is the most interesting question you can ask to get to know someone?
10.06.2025 01:10
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Why does a straight man like anal penetration?
18- How often do you drink alcohol? What is your favorite drink?
9~ How many times over your lifetime do you think you have had sex so far?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Has anyone been tricked into having sex with a shemale? How was the experience?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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?
Master/Slave Boss/Maid
Used vehicle prices ease from tariff fear-buying highs but remain elevated - CNBC
Have you ever? Care to Share?
48~ Have you ever paid or been paid for sex?
34~ Do you like the lights on or off during sex?
When you visit a store, do you go to shop or buy?
60~ How important is oral sex? Do you like receiving? Do you like giving?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Any that are a turn off?
What is your interpretation of the movie Rocky? What makes it a good film in your opinion?
If yes, what?
If you win, what will you make them do?
81~ Do you have any kinks and/or fetishes?
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- 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?
China accuses US of ‘severely violating’ trade truce - Financial Times
I would allow you to do it… What would you do to me?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Get this wrong and this could mean the end… :-) some funny, some not…
What is it like to use a Fleshlight?
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?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What would have happened if Shin was a good movie instead of a bad one?
7- What are your thoughts on religion? Is there an afterlife?
That one or two things that made you go hmmmm, OMG or wow!
9- What’s your favorite season and why? What’s your least favorite?
How is sex in college like with roommates and big campuses?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
30~ What's something unexpected that turns you on?
6- Do you have dreams? Can you remember them? What do you usually dream about?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
10- List 5 of your top pet peeves.
11- How about if they like a certain sports team? 12-How about drinking too much?
12- What is the weirdest thing you've ever eaten?
82~ Do you have any fantasies involving Role-Playing?
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)
Can you Deep Throat? Do you like the taste of yourself?
22- Do you have any birth marks? How about scars? Care to share how you got them?
65~ Describe the best orgasm you’ve ever had? Care to share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
51~ Are you willing to play adult games with your partner?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
52~ What are your hobbies?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
If you say it, I will stop, and we can talk about it when you are ready.
*** Deal Breaker Questions ***
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How many partners have you had oral sex with? Who? Care to Share?
You know that I will be 100% truthful, so ask.
31- If given a chance to be immortal, would you take it? Why?
Do you think this brought you closer together?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Would you mind if your partner watched it? How about together vs alone?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
29- How superstitious are you?
9- If you could have three wishes, what would they be? Why?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
17- Have you ever done drugs? Which ones? How often?
Prisoner/Prison Guard Landlord/Tenant
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
83~ How do you feel about Porn?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
2- What’s your favorite color? Do you a least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
28- What are some things that people do that irritate you?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
76~ Have you had a threesome? Care to Share?
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?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
What have you learned about yourself that you did not before this?
What was the longest? What was the shortest?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
19- Do/have you smoked? What do you prefer? How often?
1~ How old were you when you had your first kiss? Who? Care to Share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
62~ Have you used adult toys?
89~ Do you like taking showers together?
13~ Is there a difference between, making love, having sex, and fucking?
19- What’s your favorite fairytale? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
The Ice Breaker Questions
Family Relation Age Play
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
12- What’s your favorite food? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Would you read them together?
84~ How do you feel about reading/listening to adult stories?
29~ What are some things that turn you off? What is your biggest turn off?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
(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…)
Doctor/Nurse Stripper/Client
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
What is your favorite position? Why?
*** What’s Your Favorite…? ***
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
11~ Have you ever been caught by your parents or children or others while having sex?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
48~ Do you have any siblings? Are you close to your family?
25~ How do you feel about PDA? (Public Display of Affection)
Would /have you ever given your partner a lap dance and Striptease?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
17- What’s your favorite holiday? What’s your least favorite?
37- Do you like your name? If you could change it, what would you change it too?
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?
How old are you? Male or Female?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
92~ Everyone needs a “safe” word. What is yours?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
10- What is your favorite family tradition? What’s your least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
44~ Care to share something about yourself that no one else knows about you?
Over time has your thoughts on sex changed?
15~ Have you ever been “in love”? Who? Care to Share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
11- What's your favorite restaurant? What’s your least favorite?
92~ Have you ever had or have an STD? How many? What was it?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
4- For a pet, Cat, dog or other?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Escort/Client Job Applicant/Hiring Manager
21- What's your favorite way to spend a weekend or time off?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
49~ How many times have you been married? Why did they end?
21~ What was the best date you ever went on? What has been the worst?
1- What was your first impression of me? Has it changed?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
14- What's your favorite dessert? Do you a least favorite?
Do you like it when they show and tell you what they want?
3- What’s your favorite smell? Do you a least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Repairman/Lonely Wife Virgin/Experienced
53~ How much can you tell me about the one thing you are most passionate about?
45~ How do you feel about me blindfolding you? How about blindfolding me?
27- What was/ is nickname? Does it have a meaning behind it?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Is it ok for a man to perform oral sex after he has ejaculated inside of 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?
28~ What are some things that turn on? What is your biggest turn on?
40~ What’s the weirdest place you’ve ever had sex?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What have you learned about me that was new and/or surprising?
61~ How willing would you be to try new sexual positions?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
36~ What is your favorite time of day to have sex/make love?
70~ Would/do you have/like anal sex?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
32- What's your greatest talent? Can I see it right now?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
42~ What’s your biggest regret in life?
18~ Who/when was your first “crush”?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
5- Have you ever been hypnotized? Would you allow yourself to be?
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?
33- Beach or Mountains? Or is there another place to like better?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Nurse/Patient Celebrity/Fan
Would you ever want to be woken up with oral and/or intercourse?
8- What are your thoughts on politics?
How well do you know me? And some of your thoughts about me
Model/Photographer Police/Criminal
10~ How many dates are necessary before you to have sex with someone?
15- What's your favorite saying? What word or phrase is your least favorite?
*** Random Questions ***
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
13- How about having a certain hair cut/style?
If YES, was it with 2 men or 2 women? Did you enjoy it?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
7- What if a person smells a certain way? 8- How about smoking?
3- Should Pluto still be considered a planet? 4- How about smoking?
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…
What would you say to prove to yourself that it was really you?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
3- What Superhero or Superpower would you want to be/have?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you like the “69” position? Do you prefer to be on top or bottom?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Any that are a turn off?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
26~ What side of the bed do you sleep on?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Nothing too Serious
36- Do you play video games? What is your favorite? Do you a least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Do you watch it? What is your favorite?
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 is your view on sex? Meaning, When/Where/ How often/
22- What is your favorite childhood memory? What is your least favorite?
39~ What are your love languages?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
*** Questions About Me ***
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
33- If you could visit any time period, when would you pick? Please explain why?
*** Questions about Relationships/Past ***
51~ What tends to bring a smile to your face?
20- What’s your favorite candy? What’s your least favorite?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
38~ Share your most embarrassing sexual memory?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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,
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
1- What’s your favorite animal? 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…
Does the thought excite you? Care to share?
Would you do it again, and would you rather 2 females or 2 males?
19~ Who/when was your first “heartbreak”?
13- What’s your favorite drink? What’s your least favorite?
13- What is the craziest/scariest thing you've ever done?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
18- What’s your favorite way to relax after a long day? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
50~ How many children do you have? What are their ages?
* Give a rating for each one (0-100)
Please share Did you stop?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
14- What is an embarrassing moment in your life? How about your most embarrassing?
23- What is your dream job? What was it as a child?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Teacher/Student Stranger/One Night Stand
80~ Share your top three fantasies/desires. (Be detailed) 😊
Do you have a favorite? Is it ok if your partner does?
What is your favorite toy? Ever wanted to try a specific toy?
How many times do you think you have “made love”?
67~ Do you like it when your partner moans and/or is vocal during sex?
5~ When you first started having sex, was it what you thought it would be?
47~ What would be your dream job and why?
52~ Are you willing to make “those types” of bets with your partner?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)