What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 03:41
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?
If you win, what will you make them do?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
*** Deal Breaker Questions ***
If yes, what?
44~ Care to share something about yourself that no one else knows about you?
1- What was your first impression of me? Has it changed?
1~ How old were you when you had your first kiss? Who? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
76~ Have you had a threesome? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
How do I develop the patience to read books?
Doctor/Nurse Stripper/Client
13~ Is there a difference between, making love, having sex, and fucking?
10- What is your favorite family tradition? What’s your least favorite?
62~ Have you used adult toys?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Nothing too Serious
How does an experienced gay/bi guy handle a bi-courius guy on his first time?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Would you ever want to be woken up with oral and/or intercourse?
Over time has your thoughts on sex changed?
How do you deal with a neighbor stealing?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
5~ When you first started having sex, was it what you thought it would be?
My blog is new. I need 10 article posts for my blog. How much should I pay for it?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
45~ How do you feel about me blindfolding you? How about blindfolding me?
51~ What tends to bring a smile to your face?
Why do men prefer women below the age of 30?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
26~ What side of the bed do you sleep on?
15- What's your favorite saying? What word or phrase is your least favorite?
How can you maintain self-control?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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?
19- Do/have you smoked? What do you prefer? How often?
Is gravity just entropy rising? Long-shot idea gets another look - Hacker News
28- What are some things that people do that irritate you?
Model/Photographer Police/Criminal
6- Do you have dreams? Can you remember them? What do you usually dream about?
What is your favorite toy? Ever wanted to try a specific toy?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
8- What are your thoughts on politics?
How can I control my daily masturbating habit?
10~ How many dates are necessary before you to have sex with someone?
9- Is there something you’ve always wanted to ask me but you’re afraid?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What was your best revenge story?
21~ What was the best date you ever went on? What has been the worst?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
39~ What are your love languages?
Nutritionists Rank The Best (And Worst) Packaged Deli Meats For Your Health - HuffPost
81~ Do you have any kinks and/or fetishes?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Any that are a turn off?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
51~ Are you willing to play adult games with your partner?
11- List at least 5 things on your bucket list. Have you done any of them already?
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?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
29~ What are some things that turn you off? What is your biggest turn off?
32- What's your greatest talent? Can I see it right now?
What is your favorite position? Why?
70~ Would/do you have/like anal sex?
19~ Who/when was your first “heartbreak”?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
How many times do you think you have “made love”?
89~ Do you like taking showers together?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you think this brought you closer together?
*** Random Questions ***
3- What’s your favorite smell? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Can you Deep Throat? Do you like the taste of yourself?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
47~ What would be your dream job and why?
Do you like the “69” position? Do you prefer to be on top or bottom?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
If YES, was it with 2 men or 2 women? Did you enjoy it?
I would allow you to do it… What would you do to me?
*** Questions About Me ***
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
53~ How much can you tell me about the one thing you are most passionate about?
13- How about having a certain hair cut/style?
36- Do you play video games? What is your favorite? Do you a least favorite?
How well do you know me? And some of your thoughts about me
Have you ever? Care to Share?
Nurse/Patient Celebrity/Fan
(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…)
Do you watch it? What is your favorite?
30~ What's something unexpected that turns you on?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Repairman/Lonely Wife Virgin/Experienced
48~ Do you have any siblings? Are you close to your family?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
21- What's your favorite way to spend a weekend or time off?
Please share Did you stop?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
65~ Describe the best orgasm you’ve ever had? Care to share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Will you cheat again? How can, you be sure? Define what cheating is to you.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
14- What's your favorite dessert? Do you a least favorite?
1- What’s your favorite animal? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
That one or two things that made you go hmmmm, OMG or wow!
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Escort/Client Job Applicant/Hiring Manager
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
33- If you could visit any time period, when would you pick? Please explain why?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
* Give a rating for each one (0-100)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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 you allow me to clean every part of your body with my soapy hands and fingers?
Do you like it when they show and tell you what they want?
3- Should Pluto still be considered a planet? 4- How about smoking?
23- What is your dream job? What was it as a child?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
20- What’s your favorite candy? What’s your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
11- How about if they like a certain sports team? 12-How about drinking too much?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
*** What’s Your Favorite…? ***
12- What’s your favorite food? What’s your least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
13- What is the craziest/scariest thing you've ever done?
27- What was/ is nickname? Does it have a meaning behind it?
9- What’s your favorite season and why? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Teacher/Student Stranger/One Night Stand
52~ Are you willing to make “those types” of bets with your partner?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
8- What's your favorite flavor of ice cream? Do you a least favorite?
40~ What’s the weirdest place you’ve ever had sex?
49~ How many times have you been married? Why did they end?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
19- What’s your favorite fairytale? What’s your least favorite?
18~ Who/when was your first “crush”?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
18- How often do you drink alcohol? What is your favorite drink?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
14- What is an embarrassing moment in your life? How about your most embarrassing?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
If NO, would you ever have one? Would it be with 2 men or 2 women?
50~ How many children do you have? What are their ages?
You know that I will be 100% truthful, so ask.
2- What’s your favorite color? Do you a least favorite?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
67~ Do you like it when your partner moans and/or is vocal during sex?
Would you read them together?
Would you mind if your partner watched it? How about together vs alone?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
42~ What’s your biggest regret in life?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
25~ How do you feel about PDA? (Public Display of Affection)
What would you say to prove to yourself that it was really you?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How about if they talk dirty and/or call you names?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
10- List 5 of your top pet peeves.
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
Does the thought excite you? Care to share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
83~ How do you feel about Porn?
What do you dislike about me? I asked you to be 100% honest.
34~ Do you like the lights on or off during sex?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
71~ Would you give your partner a hand or foot job? Would you receive one?
80~ Share your top three fantasies/desires. (Be detailed) 😊
92~ Have you ever had or have an STD? How many? What was it?
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,
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Master/Slave Boss/Maid
15~ Have you ever been “in love”? Who? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
How old are you? Male or Female?
38~ Share your most embarrassing sexual memory?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
61~ How willing would you be to try new sexual positions?
7- What are your thoughts on religion? Is there an afterlife?
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
How many partners have you had oral sex with? Who? Care to Share?
What have you learned about me that was new and/or surprising?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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…
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
*** Questions about Relationships/Past ***
48~ Have you ever paid or been paid for sex?
22- What is your favorite childhood memory? What is your least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
52~ What are your hobbies?
15- What bad habit do you wish you could quit? Do you have any addictions?
28~ What are some things that turn on? What is your biggest turn on?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
84~ How do you feel about reading/listening to adult stories?
Do you have a favorite? Is it ok if your partner does?
3- What Superhero or Superpower would you want to be/have?
Family Relation Age Play
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
7- What if a person smells a certain way? 8- How about smoking?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
31- If given a chance to be immortal, would you take it? Why?
82~ Do you have any fantasies involving Role-Playing?
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Would you do it again, and would you rather 2 females or 2 males?
12- What is the weirdest thing you've ever eaten?
What was the longest? What was the shortest?
Prisoner/Prison Guard Landlord/Tenant
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
The Ice Breaker Questions
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
What have you learned about yourself that you did not before this?
Get this wrong and this could mean the end… :-) some funny, some not…
37- Do you like your name? If you could change it, what would you change it too?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
5- Have you ever been hypnotized? Would you allow yourself to be?
9~ How many times over your lifetime do you think you have had sex so far?
17- Have you ever done drugs? Which ones? How often?
33- Beach or Mountains? Or is there another place to like better?
If you say it, I will stop, and we can talk about it when you are ready.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
36~ What is your favorite time of day to have sex/make love?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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…
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)
22- Do you have any birth marks? How about scars? Care to share how you got them?
Any that are a turn off?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
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/
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
4- For a pet, Cat, dog or other?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Would /have you ever given your partner a lap dance and Striptease?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
29- How superstitious are you?
9- If you could have three wishes, what would they be? Why?