What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 01:30
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?
33- Beach or Mountains? Or is there another place to like better?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Why do men choose to marry a plain Jane woman over a pretty woman?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
13~ Is there a difference between, making love, having sex, and fucking?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Is it ok for someone to crossdress in public?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
*** Random Questions ***
21- What's your favorite way to spend a weekend or time off?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Does eating bread before bed make you fat? If so, why?
1~ How old were you when you had your first kiss? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Why are women attracted to ugly guys?
19- What’s your favorite fairytale? What’s your 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.
That one or two things that made you go hmmmm, OMG or wow!
What kind of person does a narcissist hate?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Have you ever? Care to Share?
Why am I not getting any atheists to debate with? Are they scared?
10~ How many dates are necessary before you to have sex with someone?
Get this wrong and this could mean the end… :-) some funny, some not…
26~ What side of the bed do you sleep on?
Prisoner/Prison Guard Landlord/Tenant
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
39~ What are your love languages?
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?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What would you say to prove to yourself that it was really you?
Has your mother ever walked in on you at an inappropriate time?
1- What was your first impression of me? Has it changed?
Do you like it when they show and tell you what they want?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
What are the ten cars that make me no longer feel inferior?
What is your favorite position? Why?
38~ Share your most embarrassing sexual memory?
13- What’s your favorite drink? What’s your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
9- What’s your favorite season and why? What’s your least favorite?
How well do you know me? And some of your thoughts about me
92~ Have you ever had or have an STD? How many? What was it?
9~ How many times over your lifetime do you think you have had sex so far?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
9- Is there something you’ve always wanted to ask me but you’re afraid?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
47~ What would be your dream job and why?
76~ Have you had a threesome? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
30~ What's something unexpected that turns you on?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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,
Do you have a favorite? Is it ok if your partner does?
51~ Are you willing to play adult games with your partner?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
44~ Care to share something about yourself that no one else knows about you?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
* Give a rating for each one (0-100)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
50~ How many children do you have? What are their ages?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you read them together?
23- What is your dream job? What was it as a child?
Will you cheat again? How can, you be sure? Define what cheating is to you.
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
*** What’s Your Favorite…? ***
13- What is the craziest/scariest thing you've ever done?
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…
*** Questions about Relationships/Past ***
Teacher/Student Stranger/One Night Stand
*** Questions About Me ***
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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- 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?
49~ How many times have you been married? Why did they end?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Would you do it again, and would you rather 2 females or 2 males?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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?
52~ What are your hobbies?
52~ Are you willing to make “those types” of bets with your partner?
42~ What’s your biggest regret in life?
29- How superstitious are you?
89~ Do you like taking showers together?
15~ Have you ever been “in love”? Who? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
9- If you could have three wishes, what would they be? Why?
84~ How do you feel about reading/listening to adult stories?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What is your view on sex? Meaning, When/Where/ How often/
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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
12- What is the weirdest thing you've ever eaten?
Repairman/Lonely Wife Virgin/Experienced
61~ How willing would you be to try new sexual positions?
11- What's your favorite restaurant? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
5~ When you first started having sex, was it what you thought it would be?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
You know that I will be 100% truthful, so ask.
28- What are some things that people do that irritate you?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
34~ Do you like the lights on or off during sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
1- What’s your favorite animal? Do you a least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
31- If given a chance to be immortal, would you take it? Why?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
*** Deal Breaker Questions ***
14- What's your favorite dessert? Do you a least favorite?
Escort/Client Job Applicant/Hiring Manager
18- How often do you drink alcohol? What is your favorite drink?
28~ What are some things that turn on? What is your biggest turn on?
7-What do I do in bed that drives you wild? How about, what turns you off?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you like the “69” position? Do you prefer to be on top or bottom?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
27- What was/ is nickname? Does it have a meaning behind it?
25~ How do you feel about PDA? (Public Display of Affection)
92~ Everyone needs a “safe” word. What is yours?
If yes, what?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
40~ What’s the weirdest place you’ve ever had sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
If you say it, I will stop, and we can talk about it when you are ready.
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Nurse/Patient Celebrity/Fan
3- What’s your favorite smell? Do you a least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
48~ Do you have any siblings? Are you close to your family?
81~ Do you have any kinks and/or fetishes?
8- What's your favorite flavor of ice cream? Do you a least favorite?
10- What is your favorite family tradition? What’s your least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Master/Slave Boss/Maid
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would /have you ever given your partner a lap dance and Striptease?
18~ Who/when was your first “crush”?
37- Do you like your name? If you could change it, what would you change it too?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Would you mind if your partner watched it? How about together vs alone?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
17- Have you ever done drugs? Which ones? How often?
Any that are a turn off?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
71~ Would you give your partner a hand or foot job? Would you receive one?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
3- What Superhero or Superpower would you want to be/have?
I would allow you to do it… What would you do to me?
11- List at least 5 things on your bucket list. Have you done any of them already?
(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…)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
22- Do you have any birth marks? How about scars? Care to share how you got them?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
19- Do/have you smoked? What do you prefer? How often?
How old are you? Male or Female?
11~ Have you ever been caught by your parents or children or others while having sex?
10- List 5 of your top pet peeves.
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
70~ Would/do you have/like anal sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What was the longest? What was the shortest?
Over time has your thoughts on sex changed?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Does the thought excite you? Care to share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Do you watch it? What is your favorite?
Family Relation Age Play
How about if they talk dirty and/or call you names?
15- What bad habit do you wish you could quit? Do you have any addictions?
The Ice Breaker Questions
What is your favorite toy? Ever wanted to try a specific toy?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What’s the longest time you gone without having sex, after, having it? How much time between the others?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
65~ Describe the best orgasm you’ve ever had? Care to share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Doctor/Nurse Stripper/Client
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
48~ Have you ever paid or been paid for sex?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
82~ Do you have any fantasies involving Role-Playing?
51~ What tends to bring a smile to your face?
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?
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Model/Photographer Police/Criminal
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
2- What’s your favorite color? Do you a least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
17- What’s your favorite holiday? What’s your least favorite?
Any that are a turn off?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
53~ How much can you tell me about the one thing you are most passionate about?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Do you think this brought you closer together?
Nothing too Serious
Please share Did you stop?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
4- For a pet, Cat, dog or other?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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…
36~ What is your favorite time of day to have sex/make love?
12- What’s your favorite food? What’s your least favorite?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
What have you learned about yourself that you did not before this?
67~ Do you like it when your partner moans and/or is vocal during sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
33- If you could visit any time period, when would you pick? Please explain why?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
8- What are your thoughts on politics?
If you win, what will you make them do?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
62~ Have you used adult toys?
7- What if a person smells a certain way? 8- How about smoking?
19~ Who/when was your first “heartbreak”?
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?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
13- How about having a certain hair cut/style?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What have you learned about me that was new and/or surprising?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Would you ever want to be woken up with oral and/or intercourse?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
How many times do you think you have “made love”?
15- What's your favorite saying? What word or phrase is your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
83~ How do you feel about Porn?
How many partners have you had oral sex with? Who? Care to Share?
What do you dislike about me? I asked you to be 100% honest.