What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 05:02
That one or two things that made you go hmmmm, OMG or wow!
13- What’s your favorite drink? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Do you think this Labour Party is qualified to run our country?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
25~ How do you feel about PDA? (Public Display of Affection)
7- What are your thoughts on religion? Is there an afterlife?
92~ Everyone needs a “safe” word. What is yours?
36- Do you play video games? What is your favorite? Do you a least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What's the point of gender reassignment surgery which doesn't change a person's chromosomes?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What would you say to prove to yourself that it was really you?
What is your favorite position? Why?
Why do women change that much more with age?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
9- What’s your favorite season and why? What’s your least favorite?
*** Questions about Relationships/Past ***
What is your daily motivation and does it work?
30~ What's something unexpected that turns you on?
17- What’s your favorite holiday? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
What was your most memorable experience catching a fraudulent car seller?
Master/Slave Boss/Maid
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
What a list actors/ actresses are notorious for being jerks in real life?
9~ How many times over your lifetime do you think you have had sex so far?
32- What's your greatest talent? Can I see it right now?
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?
If there is an abandoned house with no owner, can I live in it?
17- Have you ever done drugs? Which ones? How often?
Any that are a turn off?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
15- What's your favorite saying? What word or phrase is your least favorite?
48~ Have you ever paid or been paid for sex?
52~ Are you willing to make “those types” of bets with your partner?
Why are so many young teenage boys misogynistic? Where do they get these attitudes from?
62~ Have you used adult toys?
Would you do it again, and would you rather 2 females or 2 males?
3- What’s your favorite smell? Do you a least favorite?
Why is my ex trying to provoke an argument with me?
19- Do/have you smoked? What do you prefer? How often?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How about if they talk dirty and/or call you names?
Why doesn’t the UK change their flag?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
22- Do you have any birth marks? How about scars? Care to share how you got them?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Who is the most dangerous or evilest person of all time?
Have you ever? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
12- What is the weirdest thing you've ever eaten?
12- What’s your favorite food? What’s your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
4- For a pet, Cat, dog or other?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Prisoner/Prison Guard Landlord/Tenant
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…
If YES, was it with 2 men or 2 women? Did you enjoy it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Nurse/Patient Celebrity/Fan
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
19- What’s your favorite fairytale? What’s your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
3- What Superhero or Superpower would you want to be/have?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
47~ What would be your dream job and why?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Will you cheat again? How can, you be sure? Define what cheating is to you.
18- What’s your favorite way to relax after a long day? What’s your least favorite?
If yes, what?
15- What bad habit do you wish you could quit? Do you have any addictions?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
5- Have you ever been hypnotized? Would you allow yourself to be?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
13- What is the craziest/scariest thing you've ever done?
11- How about if they like a certain sports team? 12-How about drinking too much?
70~ Would/do you have/like anal sex?
What have you learned about yourself that you did not before this?
20- What’s your favorite candy? What’s your least favorite?
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?
18~ Who/when was your first “crush”?
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?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
How many times do you think you have “made love”?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
29- How superstitious are you?
What have you learned about me that was new and/or surprising?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
81~ Do you have any kinks and/or fetishes?
*** Deal Breaker Questions ***
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Please share Did you stop?
13~ Is there a difference between, making love, having sex, and fucking?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Family Relation Age Play
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?
1- What was your first impression of me? Has it changed?
Doctor/Nurse Stripper/Client
27- What was/ is nickname? Does it have a meaning behind it?
44~ Care to share something about yourself that no one else knows about you?
51~ Are you willing to play adult games with your partner?
(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…)
42~ What’s your biggest regret in life?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If you say it, I will stop, and we can talk about it when you are ready.
19~ Who/when was your first “heartbreak”?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
11- What's your favorite restaurant? What’s your least favorite?
How old are you? Male or Female?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
11~ Have you ever been caught by your parents or children or others while having sex?
Nothing too Serious
Do you think this brought you closer together?
You know that I will be 100% truthful, so ask.
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?
How well do you know me? And some of your thoughts about me
What was the longest? What was the shortest?
What do you dislike about me? I asked you to be 100% honest.
40~ What’s the weirdest place you’ve ever had sex?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
10~ How many dates are necessary before you to have sex with someone?
84~ How do you feel about reading/listening to adult stories?
Over time has your thoughts on sex changed?
Would you allow me to clean every part of your body with my soapy hands and fingers?
10- List 5 of your top pet peeves.
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
11- List at least 5 things on your bucket list. Have you done any of them already?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you like it when they show and tell you what they want?
Any that are a turn off?
*** Random Questions ***
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
36~ What is your favorite time of day to have sex/make love?
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?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
50~ How many children do you have? What are their ages?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
89~ Do you like taking showers together?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
92~ Have you ever had or have an STD? How many? What was it?
21~ What was the best date you ever went on? What has been the worst?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Model/Photographer Police/Criminal
65~ Describe the best orgasm you’ve ever had? Care to share?
83~ How do you feel about Porn?
Can you Deep Throat? Do you like the taste of yourself?
Do you watch it? What is your favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
13- How about having a certain hair cut/style?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
The Ice Breaker Questions
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
52~ What are your hobbies?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
9- If you could have three wishes, what would they be? Why?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
What is your favorite toy? Ever wanted to try a specific toy?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Escort/Client Job Applicant/Hiring Manager
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
80~ Share your top three fantasies/desires. (Be detailed) 😊
How many partners have you had oral sex with? Who? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
*** What’s Your Favorite…? ***
Would you read them together?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
34~ Do you like the lights on or off during sex?
If you win, what will you make them do?
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…
71~ Would you give your partner a hand or foot job? Would you receive one?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
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)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Teacher/Student Stranger/One Night Stand
14- What is an embarrassing moment in your life? How about your most embarrassing?
37- Do you like your name? If you could change it, what would you change it too?
28- What are some things that people do that irritate you?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
38~ Share your most embarrassing sexual memory?
45~ How do you feel about me blindfolding you? How about blindfolding me?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
21- What's your favorite way to spend a weekend or time off?
Would you mind if your partner watched it? How about together vs alone?
Repairman/Lonely Wife Virgin/Experienced
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
8- What are your thoughts on politics?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
What is your view on sex? Meaning, When/Where/ How often/
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
18- How often do you drink alcohol? What is your favorite drink?
* Give a rating for each one (0-100)
29~ What are some things that turn you off? What is your biggest turn off?
6- Do you have dreams? Can you remember them? What do you usually dream about?
49~ How many times have you been married? Why did they end?
60~ How important is oral sex? Do you like receiving? Do you like giving?
1- What’s your favorite animal? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
*** Questions About Me ***
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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,
7- What if a person smells a certain way? 8- How about smoking?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
7-What do I do in bed that drives you wild? How about, what turns you off?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
26~ What side of the bed do you sleep on?
76~ Have you had a threesome? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Does the thought excite you? Care to share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
33- If you could visit any time period, when would you pick? Please explain why?
33- Beach or Mountains? Or is there another place to like better?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
5~ When you first started having sex, was it what you thought it would be?
53~ How much can you tell me about the one thing you are most passionate about?
22- What is your favorite childhood memory? What is your least favorite?
2- What’s your favorite color? Do you a least favorite?
39~ What are your love languages?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
23- What is your dream job? What was it as a child?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
3- Should Pluto still be considered a planet? 4- How about smoking?
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)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
8- What's your favorite flavor of ice cream? Do you a least favorite?
48~ Do you have any siblings? Are you close to your family?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
61~ How willing would you be to try new sexual positions?
31- If given a chance to be immortal, would you take it? Why?
82~ Do you have any fantasies involving Role-Playing?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
28~ What are some things that turn on? What is your biggest turn on?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
I would allow you to do it… What would you do to me?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
Would /have you ever given your partner a lap dance and Striptease?
51~ What tends to bring a smile to your face?