What is the most interesting question you can ask to get to know someone?
16.06.2025 00:06
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
13- How about having a certain hair cut/style?
If you received hand-me-downs as a child, how did they make you feel?
Please share Did you stop?
50~ How many children do you have? What are their ages?
Any that are a turn off?
28~ What are some things that turn on? What is your biggest turn on?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Can you share a picture of your favorite outfit and explain why you love it?
36- Do you play video games? What is your favorite? Do you a least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What should I do to get over a relationship?
3- Should Pluto still be considered a planet? 4- How about smoking?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
How many times do you think you have “made love”?
What’s the best way to get over someone you love?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What firsthand information do you have on prisoner-on-prisoner sexual abuse/rape?
What do you dislike about me? I asked you to be 100% honest.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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?
Are Turks ashamed of their Islamic heritage?
Repairman/Lonely Wife Virgin/Experienced
If NO, would you ever have one? Would it be with 2 men or 2 women?
92~ Have you ever had or have an STD? How many? What was it?
Can anyone or anything overthrow your belief in the Jewish God?
*** Questions About Me ***
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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…
I'm pretty sure that my dog is transgender, how would I go about transitioning it?
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?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Why do some men like anal sex?
Do you have a favorite? Is it ok if your partner does?
30~ What's something unexpected that turns you on?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
44~ Care to share something about yourself that no one else knows about you?
71~ Would you give your partner a hand or foot job? Would you receive one?
1- What’s your favorite animal? Do you a least favorite?
How many girls or guys keep extra pantyhose in their glove box or console of their vehicle?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
7- What are your thoughts on religion? Is there an afterlife?
15~ Have you ever been “in love”? Who? Care to Share?
Why is Reddit blocked by the Indonesian government?
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
9~ How many times over your lifetime do you think you have had sex so far?
Do you suck dicks with no reciprocation?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What is your favorite toy? Ever wanted to try a specific toy?
19- What’s your favorite fairytale? What’s your least favorite?
How well do you know me? And some of your thoughts about me
11- List at least 5 things on your bucket list. Have you done any of them already?
92~ Everyone needs a “safe” word. What is yours?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
5- Have you ever been hypnotized? Would you allow yourself to be?
45~ How do you feel about me blindfolding you? How about blindfolding me?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
34~ Do you like the lights on or off during sex?
48~ Do you have any siblings? Are you close to your family?
Family Relation Age Play
17- Have you ever done drugs? Which ones? How often?
17- What’s your favorite holiday? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
13- What’s your favorite drink? What’s your least favorite?
4- For a pet, Cat, dog or other?
40~ What’s the weirdest place you’ve ever had sex?
14- What's your favorite dessert? Do you a least favorite?
31- If given a chance to be immortal, would you take it? Why?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
39~ What are your love languages?
53~ How much can you tell me about the one thing you are most passionate about?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
52~ Are you willing to make “those types” of bets with your partner?
83~ How do you feel about Porn?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
36~ What is your favorite time of day to have sex/make love?
29~ What are some things that turn you off? What is your biggest turn off?
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?
9- If you could have three wishes, what would they be? Why?
What have you learned about yourself that you did not before this?
That one or two things that made you go hmmmm, OMG or wow!
21~ What was the best date you ever went on? What has been the worst?
18- How often do you drink alcohol? What is your favorite drink?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
13~ Is there a difference between, making love, having sex, and fucking?
51~ Are you willing to play adult games with your partner?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
3- What Superhero or Superpower would you want to be/have?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
How many partners have you had oral sex with? Who? Care to Share?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
1- What was your first impression of me? Has it changed?
*** Random Questions ***
38~ Share your most embarrassing sexual memory?
89~ Do you like taking showers together?
11- How about if they like a certain sports team? 12-How about drinking too much?
13- What is the craziest/scariest thing you've ever done?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
2- What’s your favorite color? Do you a least favorite?
26~ What side of the bed do you sleep on?
11- What's your favorite restaurant? What’s your least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you think this brought you closer together?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
What was the longest? What was the shortest?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
* Give a rating for each one (0-100)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
15- What's your favorite saying? What word or phrase is your least favorite?
7- What if a person smells a certain way? 8- How about smoking?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Nurse/Patient Celebrity/Fan
27- What was/ is nickname? Does it have a meaning behind it?
5~ When you first started having sex, was it what you thought it would be?
84~ How do you feel about reading/listening to adult stories?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
47~ What would be your dream job and why?
If you say it, I will stop, and we can talk about it when you are ready.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
(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…)
29- How superstitious are you?
11~ Have you ever been caught by your parents or children or others while having sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
82~ Do you have any fantasies involving Role-Playing?
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?
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?
61~ How willing would you be to try new sexual positions?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
67~ Do you like it when your partner moans and/or is vocal during sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Teacher/Student Stranger/One Night Stand
*** Questions about Relationships/Past ***
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
62~ Have you used adult toys?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How about if they talk dirty and/or call you names?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
If you lose, are you willing to be their sex slave for a day, (anything goes)?
25~ How do you feel about PDA? (Public Display of Affection)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
20- What’s your favorite candy? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Nothing too Serious
*** What’s Your Favorite…? ***
What have you learned about me that was new and/or surprising?
48~ Have you ever paid or been paid for sex?
9- What’s your favorite season and why? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
28- What are some things that people do that irritate you?
52~ What are your hobbies?
Any that are a turn off?
Do you watch it? What is your favorite?
42~ What’s your biggest regret in life?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
I would allow you to do it… What would you do to me?
Would you mind if your partner watched it? How about together vs alone?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Prisoner/Prison Guard Landlord/Tenant
24~ What are your expectations in a relationship? (I know a very big question, take your time)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
33- If you could visit any time period, when would you pick? Please explain why?
Would /have you ever given your partner a lap dance and Striptease?
How old are you? Male or Female?
65~ Describe the best orgasm you’ve ever had? Care to share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Do you like the “69” position? Do you prefer to be on top or bottom?
19~ Who/when was your first “heartbreak”?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
10- List 5 of your top pet peeves.
8- What are your thoughts on politics?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
12- What is the weirdest thing you've ever eaten?
12- What’s your favorite food? What’s your least favorite?
81~ Do you have any kinks and/or fetishes?
Do you like it when they show and tell you what they want?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
10~ How many dates are necessary before you to have sex with someone?
18~ Who/when was your first “crush”?
Doctor/Nurse Stripper/Client
14- What is an embarrassing moment in your life? How about your most embarrassing?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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?
70~ Would/do you have/like anal sex?
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?
49~ How many times have you been married? Why did they end?
Over time has your thoughts on sex changed?
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,
3- What’s your favorite smell? Do you a least favorite?
51~ What tends to bring a smile to your face?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
What is your view on sex? Meaning, When/Where/ How often/
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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…
33- Beach or Mountains? Or is there another place to like better?
Does the thought excite you? Care to share?
*** Deal Breaker Questions ***
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
32- What's your greatest talent? Can I see it right now?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Would you read them together?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
10- What is your favorite family tradition? What’s your least favorite?
You know that I will be 100% truthful, so ask.
Escort/Client Job Applicant/Hiring Manager
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
23- What is your dream job? What was it as a child?
76~ Have you had a threesome? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
What would you say to prove to yourself that it was really you?
Will you cheat again? How can, you be sure? Define what cheating is to you.
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
7-What do I do in bed that drives you wild? How about, what turns you off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
If yes, what?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
Model/Photographer Police/Criminal
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
37- Do you like your name? If you could change it, what would you change it too?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
What is your favorite position? Why?
Have you ever? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
8- What's your favorite flavor of ice cream? Do you a least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Can you Deep Throat? Do you like the taste of yourself?
Master/Slave Boss/Maid
34- Ever been to a concert? What was your favorite? Who would you like to see?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?