What is the most interesting question you can ask to get to know someone?
10.06.2025 02:27
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What have you learned about me that was new and/or surprising?
Doctor/Nurse Stripper/Client
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
44~ Care to share something about yourself that no one else knows about you?
37- Do you like your name? If you could change it, what would you change it too?
What is your favorite underrated movie and why? What makes it underrated? How did you find it?
48~ Have you ever paid or been paid for sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Why do British people always write "xxx" after their names?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
82~ Do you have any fantasies involving Role-Playing?
Master/Slave Boss/Maid
What would explain Trump blaming Ukraine for starting the war with Russia?
42~ What’s your biggest regret in life?
13- What is the craziest/scariest thing you've ever done?
11- List at least 5 things on your bucket list. Have you done any of them already?
Will you cheat again? How can, you be sure? Define what cheating is to you.
8- What's your favorite flavor of ice cream? Do you a least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Why do men love boobs (irrespective of big or small)?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Have you ever? Care to Share?
Do you watch it? What is your favorite?
Don't miss the half-lit first quarter moon rise tonight — Here's what to look for - Space
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
9~ How many times over your lifetime do you think you have had sex so far?
If people in the UK hate Trump so much, why does he own golf courses there?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
29~ What are some things that turn you off? What is your biggest turn off?
12- What is the weirdest thing you've ever eaten?
Get this wrong and this could mean the end… :-) some funny, some not…
39~ What are your love languages?
How did Kate Mulgrew feel about Jeri Ryan joining the cast of Star Trek: Voyager?
Please share Did you stop?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
I have a bad reputation and need help. What should I do?
Teacher/Student Stranger/One Night Stand
How old are you? Male or Female?
5- Have you ever been hypnotized? Would you allow yourself to be?
Have you ever been forced to dress like a girl?
What have you learned about yourself that you did not before this?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
11- How about if they like a certain sports team? 12-How about drinking too much?
What does success really mean to you? Is it about happiness, money, or something else?
11- What's your favorite restaurant? What’s your least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
How about if they talk dirty and/or call you names?
Need For Speed Underground 2 remake leaves fans absolutely floored - GAMINGbible
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 shave your legs? How about your pubic hair? How about shower sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Is it okay for my husband to help other ladies without telling me?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
28~ What are some things that turn on? What is your biggest turn on?
15- What's your favorite saying? What word or phrase is your least favorite?
* 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?
21- What's your favorite way to spend a weekend or time off?
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?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
52~ Are you willing to make “those types” of bets with your partner?
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
28- What are some things that people do that irritate you?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
18- How often do you drink alcohol? What is your favorite drink?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
*** Questions about Relationships/Past ***
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
(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…)
Would you allow me to clean every part of your body with my soapy hands and fingers?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
62~ Have you used adult toys?
What is your favorite toy? Ever wanted to try a specific toy?
60~ How important is oral sex? Do you like receiving? Do you like giving?
51~ Are you willing to play adult games with your partner?
92~ Everyone needs a “safe” word. What is yours?
What would you say to prove to yourself that it was really you?
Would you read them together?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
3- What Superhero or Superpower would you want to be/have?
18~ Who/when was your first “crush”?
76~ Have you had a threesome? Care to Share?
13- What’s your favorite drink? 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?
*** Deal Breaker Questions ***
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
How many partners have you had oral sex with? Who? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Do you like the “69” position? Do you prefer to be on top or bottom?
27- What was/ is nickname? Does it have a meaning behind it?
70~ Would/do you have/like anal sex?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
14- What's your favorite dessert? 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?
*** Random Questions ***
6- Do you have dreams? Can you remember them? What do you usually dream about?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
49~ How many times have you been married? Why did they end?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
11~ Have you ever been caught by your parents or children or others while having sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
36- Do you play video games? What is your favorite? Do you a least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
30~ What's something unexpected that turns you on?
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?
13~ Is there a difference between, making love, having sex, and fucking?
7- What if a person smells a certain way? 8- 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…
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Repairman/Lonely Wife Virgin/Experienced
29- How superstitious are you?
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)
5~ When you first started having sex, was it what you thought it would be?
If NO, would you ever have one? Would it be with 2 men or 2 women?
17- Have you ever done drugs? Which ones? How often?
If you say it, I will stop, and we can talk about it when you are ready.
Do you have a favorite? Is it ok if your partner does?
61~ How willing would you be to try new sexual positions?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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/
64~ When was your very first orgasm? When was your first from having sex? Care to share?
50~ How many children do you have? What are their ages?
1- What’s your favorite animal? Do you a least favorite?
1- What was your first impression of me? Has it changed?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
9- What’s your favorite season and why? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
26~ What side of the bed do you sleep on?
Do you think this brought you closer together?
71~ Would you give your partner a hand or foot job? Would you receive one?
17- What’s your favorite holiday? What’s your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? 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?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
51~ What tends to bring a smile to your face?
19- What’s your favorite fairytale? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
38~ Share your most embarrassing sexual memory?
22- What is your favorite childhood memory? What is your least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
10- List 5 of your top pet peeves.
*** Questions About Me ***
Family Relation Age Play
*** What’s Your Favorite…? ***
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
4- For a pet, Cat, dog or other?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Can you Deep Throat? Do you like the taste of yourself?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
67~ Do you like it when your partner moans and/or is vocal during sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
40~ What’s the weirdest place you’ve ever had sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you ever want to be woken up with oral and/or intercourse?
33- Beach or Mountains? Or is there another place to like better?
32- What's your greatest talent? Can I see it right now?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Would /have you ever given your partner a lap dance and Striptease?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
53~ How much can you tell me about the one thing you are most passionate about?
2- What’s your favorite color? Do you a least favorite?
Nothing too Serious
Nurse/Patient Celebrity/Fan
That one or two things that made you go hmmmm, OMG or wow!
What is your favorite position? Why?
83~ How do you feel about Porn?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
23- What is your dream job? What was it as a child?
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?
How many times do you think you have “made love”?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
15~ Have you ever been “in love”? Who? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
12- What’s your favorite food? What’s your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
89~ Do you like taking showers together?
You know that I will be 100% truthful, so ask.
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
7-What do I do in bed that drives you wild? How about, what turns you off?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If yes, what?
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
19- Do/have you smoked? What do you prefer? How often?
Over time has your thoughts on sex changed?
Model/Photographer Police/Criminal
81~ Do you have any kinks and/or fetishes?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Do you like it when they show and tell you what they want?
20- What’s your favorite candy? What’s your least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
65~ Describe the best orgasm you’ve ever had? Care to share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Any that are a turn off?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Would you mind if your partner watched it? How about together vs alone?
47~ What would be your dream job and why?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
19~ Who/when was your first “heartbreak”?
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…
48~ Do you have any siblings? Are you close to your family?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
22- Do you have any birth marks? How about scars? Care to share how you got them?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
10~ How many dates are necessary before you to have sex with someone?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If you win, what will you make them do?
34~ Do you like the lights on or off during sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
31- If given a chance to be immortal, would you take it? Why?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
* Give a rating for each one (0-100)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
36~ What is your favorite time of day to have sex/make love?
1~ How old were you when you had your first kiss? Who? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
What was the longest? What was the shortest?
Escort/Client Job Applicant/Hiring Manager
3- What’s your favorite smell? Do you a least favorite?
I would allow you to do it… What would you do to me?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What do you dislike about me? I asked you to be 100% honest.
Any that are a turn off?
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
7- What are your thoughts on religion? Is there an afterlife?
Does the thought excite you? Care to share?
84~ How do you feel about reading/listening to adult stories?
The Ice Breaker Questions
9- If you could have three wishes, what would they be? Why?
52~ What are your hobbies?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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,
21~ What was the best date you ever went on? What has been the worst?
Prisoner/Prison Guard Landlord/Tenant
How well do you know me? And some of your thoughts about me
41~ Are there moments in your past that you would want to change? Please share 3 of them.
92~ Have you ever had or have an STD? How many? What was it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
10- What is your favorite family tradition? What’s your least favorite?
7~ How many times in one day have you had sex? Who/When/Where? 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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?