What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 03:13
13- What is the craziest/scariest thing you've ever done?
I would allow you to do it… What would you do to me?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Do you think this brought you closer together?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Can you Deep Throat? Do you like the taste of yourself?
Does the West have a defense against China's PL17 air-air missile?
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?
What have you learned about yourself that you did not before this?
51~ Are you willing to play adult games with your partner?
Have you ever gone to a porn theater with your wife?
4- For a pet, Cat, dog or other?
How old are you? Male or Female?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What's the most sordid activity you've ever seen or heard about at a bachelorette party?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Why is Donald Trump criticized by so many people?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
33- If you could visit any time period, when would you pick? Please explain why?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do empaths fall easier for abusive people?
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?
That one or two things that made you go hmmmm, OMG or wow!
How do I develop the patience to read books?
22- Do you have any birth marks? How about scars? Care to share how you got them?
29~ What are some things that turn you off? What is your biggest turn off?
84~ How do you feel about reading/listening to adult stories?
I am 13 and I am planning to run away. What should I do to succeed?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
What is your view on sex? Meaning, When/Where/ How often/
What are the most shocking facts about the Bollywood industry?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
What are some tips for a girl with low self-esteem to start dating?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
17- Have you ever done drugs? Which ones? How often?
52~ What are your hobbies?
Common herbal supplement used to beat stress linked to liver toxicity - Times of India
3- Should Pluto still be considered a planet? 4- How about smoking?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
What do you dislike about me? I asked you to be 100% honest.
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
(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…)
31- If given a chance to be immortal, would you take it? Why?
How does a man look at you when he is in love?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Prisoner/Prison Guard Landlord/Tenant
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?
Can you tell me a depressing story?
How many times do you think you have “made love”?
13- What’s your favorite drink? What’s your least favorite?
What have you learned about me that was new and/or surprising?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Any that are a turn off?
37- Do you like your name? If you could change it, what would you change it too?
*** Questions About Me ***
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
9~ How many times over your lifetime do you think you have had sex so far?
19- Do/have you smoked? What do you prefer? How often?
12- What’s your favorite food? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
12- What is the weirdest thing you've ever eaten?
92~ Have you ever had or have an STD? How many? What was it?
*** Deal Breaker Questions ***
Family Relation Age Play
Escort/Client Job Applicant/Hiring Manager
30~ What's something unexpected that turns you on?
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
6- Do you have dreams? Can you remember them? What do you usually dream about?
* Give a rating for each one (0-100)
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
1- What was your first impression of me? Has it changed?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would you mind if your partner watched it? How about together vs alone?
Teacher/Student Stranger/One Night Stand
3- What Superhero or Superpower would you want to be/have?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
28- What are some things that people do that irritate you?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
25~ How do you feel about PDA? (Public Display of Affection)
17- What’s your favorite holiday? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
15~ Have you ever been “in love”? Who? Care to Share?
21- What's your favorite way to spend a weekend or time off?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Do you like the “69” position? Do you prefer to be on top or bottom?
67~ Do you like it when your partner moans and/or is vocal during sex?
2- What’s your favorite color? Do you a least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
38~ Share your most embarrassing sexual memory?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
15- What bad habit do you wish you could quit? Do you have any addictions?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Doctor/Nurse Stripper/Client
Do you watch it? What is your favorite?
Do you like it when they show and tell you what they want?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
65~ Describe the best orgasm you’ve ever had? Care to share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
82~ Do you have any fantasies involving Role-Playing?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
7- What if a person smells a certain way? 8- How about smoking?
How well do you know me? And some of your thoughts about me
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?
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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Repairman/Lonely Wife Virgin/Experienced
9- If you could have three wishes, what would they be? Why?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
19~ Who/when was your first “heartbreak”?
*** Questions about Relationships/Past ***
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Over time has your thoughts on sex changed?
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Have you ever? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
Would /have you ever given your partner a lap dance and Striptease?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
22- What is your favorite childhood memory? What is your least favorite?
49~ How many times have you been married? Why did they end?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
If you win, what will you make them do?
9- What’s your favorite season and why? What’s your least favorite?
3- What’s your favorite smell? Do you a least favorite?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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,
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
8- What are your thoughts on politics?
48~ Have you ever paid or been paid for sex?
11- How about if they like a certain sports team? 12-How about drinking too much?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Do you shave/trim your pubic hair? For you guys do you shave your balls?
How many partners have you had oral sex with? Who? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
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?
13~ Is there a difference between, making love, having sex, and fucking?
70~ Would/do you have/like anal sex?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
29- How superstitious are you?
1~ How old were you when you had your first kiss? Who? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
15- What's your favorite saying? What word or phrase is your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
32- What's your greatest talent? Can I see it right now?
18~ Who/when was your first “crush”?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What was the longest? What was the shortest?
11- What's your favorite restaurant? What’s your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
What is your favorite position? Why?
19- What’s your favorite fairytale? What’s your least favorite?
How about if they talk dirty and/or call you names?
Do you have a favorite? Is it ok if your partner does?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
14- What's your favorite dessert? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
39~ What are your love languages?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
34~ Do you like the lights on or off during sex?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
18- What’s your favorite way to relax after a long day? 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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Please share Did you stop?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
13- How about having a certain hair cut/style?
40~ What’s the weirdest place you’ve ever had sex?
7- What are your thoughts on religion? Is there an afterlife?
You know that I will be 100% truthful, so ask.
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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…
10~ How many dates are necessary before you to have sex with someone?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
27- What was/ is nickname? Does it have a meaning behind it?
18- How often do you drink alcohol? What is your favorite drink?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
1- What’s your favorite animal? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
26~ What side of the bed do you sleep on?
8- What's your favorite flavor of ice cream? Do you a least favorite?
81~ Do you have any kinks and/or fetishes?
20- What’s your favorite candy? What’s your least favorite?
Does the thought excite you? Care to share?
28~ What are some things that turn on? What is your biggest turn on?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
61~ How willing would you be to try new sexual positions?
10- List 5 of your top pet peeves.
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
If you say it, I will stop, and we can talk about it when you are ready.
76~ Have you had a threesome? Care to Share?
The Ice Breaker Questions
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…
Model/Photographer Police/Criminal
If yes, what?
34- Ever been to a concert? What was your favorite? Who would you like to see?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
11- List at least 5 things on your bucket list. Have you done any of them already?
10- What is your favorite family tradition? What’s your least favorite?
47~ What would be your dream job and why?
92~ Everyone needs a “safe” word. What is yours?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
45~ How do you feel about me blindfolding you? How about blindfolding me?
42~ What’s your biggest regret in life?
89~ Do you like taking showers together?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
33- Beach or Mountains? Or is there another place to like better?
Would you read them together?
50~ How many children do you have? What are their ages?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Master/Slave Boss/Maid
48~ Do you have any siblings? Are you close to your family?
What would you say to prove to yourself that it was really you?
Nothing too Serious
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)
36- Do you play video games? What is your favorite? Do you a least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Would you do it again, and would you rather 2 females or 2 males?
21~ What was the best date you ever went on? What has been the worst?
62~ Have you used adult toys?
Any that are a turn off?
*** What’s Your Favorite…? ***
What’s the longest time you gone without having sex, after, having it? How much time between the others?
36~ What is your favorite time of day to have sex/make love?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
51~ What tends to bring a smile to your face?
11~ Have you ever been caught by your parents or children or others while having sex?
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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
7-What do I do in bed that drives you wild? How about, what turns you off?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
83~ How do you feel about Porn?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Nurse/Patient Celebrity/Fan
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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?
What is your favorite toy? Ever wanted to try a specific toy?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
*** Random Questions ***