What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 06:20
You know that I will be 100% truthful, so ask.
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
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?
84~ How do you feel about reading/listening to adult stories?
50~ How many children do you have? What are their ages?
Any that are a turn off?
28- What are some things that people do that irritate you?
Which city should one visit between Nice and Cannes? Why?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
What’s one positive trait you’ve gained because of BPD?
14- What is an embarrassing moment in your life? How about your most embarrassing?
49~ How many times have you been married? Why did they end?
(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…)
Over time has your thoughts on sex changed?
Doctor/Nurse Stripper/Client
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
15~ Have you ever been “in love”? Who? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
10~ How many dates are necessary before you to have sex with someone?
How did you react when your doctor ordered a colonoscopy?
How many partners have you had oral sex with? Who? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
48~ Have you ever paid or been paid for sex?
Is there an MBTI personality that is more or less likely to handle stress?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
38~ Share your most embarrassing sexual memory?
What is your favorite position? Why?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
71~ Would you give your partner a hand or foot job? Would you receive one?
Why do I like to eat my own cum?
26~ What side of the bed do you sleep on?
89~ Do you like taking showers together?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Is it legal for an employer to ask why you are taking time off from work?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
*** Deal Breaker Questions ***
What should I do to get over a relationship?
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…
18- How often do you drink alcohol? What is your favorite drink?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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If you lose, are you willing to be their sex slave for a day, (anything goes)?
76~ Have you had a threesome? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
22- Do you have any birth marks? How about scars? Care to share how you got them?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
Do you think this brought you closer together?
29- How superstitious are you?
11- List at least 5 things on your bucket list. Have you done any of them already?
9- What’s your favorite season and why? What’s your least favorite?
52~ What are your hobbies?
Please share Did you stop?
9- Is there something you’ve always wanted to ask me but you’re afraid?
13- What is the craziest/scariest thing you've ever done?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
14- What's your favorite dessert? Do you a least favorite?
18~ Who/when was your first “crush”?
9~ How many times over your lifetime do you think you have had sex so far?
92~ Have you ever had or have an STD? How many? What was it?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
8- What are your thoughts on politics?
*** Questions about Relationships/Past ***
13- What’s your favorite drink? What’s your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Do you like it when they show and tell you what they want?
64~ When was your very first orgasm? When was your first from having sex? 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,
81~ Do you have any kinks and/or fetishes?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
1~ How old were you when you had your first kiss? Who? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Would you read them together?
Nurse/Patient Celebrity/Fan
How well do you know me? And some of your thoughts about me
11- How about if they like a certain sports team? 12-How about drinking too much?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What was the longest? What was the shortest?
33- If you could visit any time period, when would you pick? Please explain why?
That one or two things that made you go hmmmm, OMG or wow!
33- Beach or Mountains? Or is there another place to like better?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Master/Slave Boss/Maid
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65~ Describe the best orgasm you’ve ever had? Care to share?
How old are you? Male or Female?
25~ How do you feel about PDA? (Public Display of Affection)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
21~ What was the best date you ever went on? What has been the worst?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
*** Questions About Me ***
Would /have you ever given your partner a lap dance and Striptease?
10- List 5 of your top pet peeves.
12- What is the weirdest thing you've ever eaten?
Would you ever want to be woken up with oral and/or intercourse?
I would allow you to do it… What would you do to me?
Repairman/Lonely Wife Virgin/Experienced
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”?
9- If you could have three wishes, what would they be? Why?
What is your view on sex? Meaning, When/Where/ How often/
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Nothing too Serious
51~ What tends to bring a smile to your face?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
32- What's your greatest talent? Can I see it right now?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
28~ What are some things that turn on? What is your biggest turn on?
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- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
31- If given a chance to be immortal, would you take it? Why?
If yes, what?
Can you Deep Throat? Do you like the taste of yourself?
1- What’s your favorite animal? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
10- What is your favorite family tradition? What’s your least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
How about if they talk dirty and/or call you names?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
62~ Have you used adult toys?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
83~ How do you feel about Porn?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
48~ Do you have any siblings? Are you close to your family?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Family Relation Age Play
11~ Have you ever been caught by your parents or children or others while having sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
80~ Share your top three fantasies/desires. (Be detailed) 😊
3- What was the most surprising thing you’ve learned about me throughout our relationship?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
17- What’s your favorite holiday? What’s your least favorite?
13- How about having a certain hair cut/style?
Would you do it again, and would you rather 2 females or 2 males?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Escort/Client Job Applicant/Hiring Manager
The Ice Breaker Questions
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
42~ What’s your biggest regret in life?
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?
17- Have you ever done drugs? Which ones? How often?
27- What was/ is nickname? Does it have a meaning behind it?
Does the thought excite you? Care to share?
22- What is your favorite childhood memory? What is your least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
15- What's your favorite saying? What word or phrase is your least favorite?
What would you say to prove to yourself that it was really you?
19~ Who/when was your first “heartbreak”?
What is your favorite toy? Ever wanted to try a specific toy?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
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?
Do you have a favorite? Is it ok if your partner does?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
12- What’s your favorite food? What’s your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Have you ever? Care to Share?
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?
37- Do you like your name? If you could change it, what would you change it too?
23- What is your dream job? What was it as a child?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
3- What Superhero or Superpower would you want to be/have?
51~ Are you willing to play adult games with your partner?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Would you allow me to clean every part of your body with my soapy hands and fingers?
36~ What is your favorite time of day to have sex/make love?
70~ Would/do you have/like anal sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
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?
If YES, was it with 2 men or 2 women? Did you enjoy it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
3- Should Pluto still be considered a planet? 4- How about smoking?
Teacher/Student Stranger/One Night Stand
Will you cheat again? How can, you be sure? Define what cheating is to you.
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
40~ What’s the weirdest place you’ve ever had sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
1- What was your first impression of me? Has it changed?
21- What's your favorite way to spend a weekend or time off?
5~ When you first started having sex, was it what you thought it would be?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
60~ How important is oral sex? Do you like receiving? Do you like giving?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
*** Random Questions ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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?
30~ What's something unexpected that turns you on?
4- For a pet, Cat, dog or other?
15- What bad habit do you wish you could quit? Do you have any addictions?
What have you learned about me that was new and/or surprising?
52~ Are you willing to make “those types” of bets with your partner?
7- What are your thoughts on religion? Is there an afterlife?
6- Do you have dreams? Can you remember them? What do you usually dream about?
7- What if a person smells a certain way? 8- How about smoking?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
* Give a rating for each one (0-100)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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…
20- What’s your favorite candy? What’s your least favorite?
What have you learned about yourself that you did not before this?
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?
Any that are a turn off?
92~ Everyone needs a “safe” word. What is yours?
Would you mind if your partner watched it? How about together vs alone?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
29~ What are some things that turn you off? What is your biggest turn off?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
61~ How willing would you be to try new sexual positions?
Model/Photographer Police/Criminal
67~ Do you like it when your partner moans and/or is vocal during sex?
44~ Care to share something about yourself that no one else knows about you?
Is it ok for a man to perform oral sex after he has ejaculated inside of 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)
11- What's your favorite restaurant? What’s your least favorite?
What do you dislike about me? I asked you to be 100% honest.
47~ What would be your dream job and why?
Get this wrong and this could mean the end… :-) some funny, some not…
Do you like the “69” position? Do you prefer to be on top or bottom?
19- What’s your favorite fairytale? What’s your least favorite?
39~ What are your love languages?
Do you watch it? What is your favorite?
34~ Do you like the lights on or off during sex?
If you win, what will you make them do?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
2- What’s your favorite color? 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.
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
If you say it, I will stop, and we can talk about it when you are ready.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** What’s Your Favorite…? ***