What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 02:43
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
How old are you? Male or Female?
Repairman/Lonely Wife Virgin/Experienced
What are the most extreme examples of hypocrisy?
Does the thought excite you? Care to share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
I would allow you to do it… What would you do to me?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
Does the West have a defense against China's PL17 air-air missile?
13- What is the craziest/scariest thing you've ever done?
1- What was your first impression of me? Has it changed?
Do you watch it? What is your favorite?
20- What’s your favorite candy? What’s your least favorite?
(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…)
How well do you know me? And some of your thoughts about me
Why do men choose to marry a plain Jane woman over a pretty woman?
Master/Slave Boss/Maid
61~ How willing would you be to try new sexual positions?
13~ Is there a difference between, making love, having sex, and fucking?
What is your craziest/worst Halloween story?
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?
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?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Have you ever regretted not hitting on a older women?
83~ How do you feel about Porn?
If YES, was it with 2 men or 2 women? Did you enjoy it?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Why am I so tired of the keto diet?
What is your favorite position? Why?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
8- What are your thoughts on politics?
Is the 4B movement's aggressiveness against men for seeing women as mantelpieces valid?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
If you win, what will you make them do?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Why are American women so ugly nowadays?
36- Do you play video games? What is your favorite? Do you a least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
30~ What's something unexpected that turns you on?
What have you learned about me that was new and/or surprising?
15~ Have you ever been “in love”? Who? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
Xbox Surprises Users With Free Copy of One of its Biggest Games - ComicBook.com
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
How did you become popular in school?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
*** What’s Your Favorite…? ***
Why do some children hate their parents?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
If yes, what?
Model/Photographer Police/Criminal
33- Beach or Mountains? Or is there another place to like better?
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?
19~ Who/when was your first “heartbreak”?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
8- What's your favorite flavor of ice cream? Do you a least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you read them together?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Please share Did you stop?
7- What if a person smells a certain way? 8- How about smoking?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
82~ Do you have any fantasies involving Role-Playing?
81~ Do you have any kinks and/or fetishes?
How many times do you think you have “made love”?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
45~ How do you feel about me blindfolding you? How about blindfolding me?
11~ Have you ever been caught by your parents or children or others while having sex?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
What do you dislike about me? I asked you to be 100% honest.
That one or two things that made you go hmmmm, OMG or wow!
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
11- List at least 5 things on your bucket list. Have you done any of them already?
Nurse/Patient Celebrity/Fan
3- What Superhero or Superpower would you want to be/have?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
42~ What’s your biggest regret in life?
39~ What are your love languages?
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~ 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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
2- What’s your favorite color? Do you a least favorite?
50~ How many children do you have? What are their ages?
34~ Do you like the lights on or off during sex?
13- How about having a certain hair cut/style?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Nothing too Serious
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
32- What's your greatest talent? Can I see it right now?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Any that are a turn off?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
48~ Do you have any siblings? Are you close to your family?
Would /have you ever given your partner a lap dance and Striptease?
9- Is there something you’ve always wanted to ask me but you’re afraid?
47~ What would be your dream job and why?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
40~ What’s the weirdest place you’ve ever had sex?
22- What is your favorite childhood memory? What is your least favorite?
44~ Care to share something about yourself that no one else knows about you?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
28~ What are some things that turn on? What is your biggest turn on?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
38~ Share your most embarrassing sexual memory?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
53~ How much can you tell me about the one thing you are most passionate about?
*** Questions About Me ***
* Give a rating for each one (0-100)
10- List 5 of your top pet peeves.
3- What’s your favorite smell? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
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?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
10- What is your favorite family tradition? What’s your least favorite?
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…
Get this wrong and this could mean the end… :-) some funny, some not…
9~ How many times over your lifetime do you think you have had sex so far?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
If NO, would you ever have one? Would it be with 2 men or 2 women?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
*** Deal Breaker Questions ***
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
17- What’s your favorite holiday? What’s your least favorite?
92~ Have you ever had or have an STD? How many? What was it?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
25~ How do you feel about PDA? (Public Display of Affection)
51~ What tends to bring a smile to your face?
Over time has your thoughts on sex changed?
12- What is the weirdest thing you've ever eaten?
26~ What side of the bed do you sleep on?
37- Do you like your name? If you could change it, what would you change it too?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
15- What's your favorite saying? What word or phrase is your least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
22- Do you have any birth marks? How about scars? Care to share how you got them?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
Have you ever? Care to Share?
12- What’s your favorite food? What’s your least favorite?
76~ Have you had a threesome? Care to Share?
Do you have a favorite? Is it ok if your partner does?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
28- What are some things that people do that irritate you?
*** Random Questions ***
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
29- How superstitious are you?
Doctor/Nurse Stripper/Client
*** Questions about Relationships/Past ***
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
48~ Have you ever paid or been paid for sex?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
13- What’s your favorite drink? What’s your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
27- What was/ is nickname? Does it have a meaning behind it?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
5~ When you first started having sex, was it what you thought it would be?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
What would you say to prove to yourself that it was really you?
80~ Share your top three fantasies/desires. (Be detailed) 😊
5- Have you ever been hypnotized? Would you allow yourself to be?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
17- Have you ever done drugs? Which ones? How often?
1~ How old were you when you had your first kiss? Who? Care to Share?
Family Relation Age Play
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
89~ Do you like taking showers together?
23- What is your dream job? What was it as a child?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
62~ Have you used adult toys?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
92~ Everyone needs a “safe” word. What is yours?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
1- What’s your favorite animal? Do you a least favorite?
36~ What is your favorite time of day to have sex/make love?
How many partners have you had oral sex with? Who? Care to Share?
Do you like the “69” position? Do you prefer to be on top or bottom?
21~ What was the best date you ever went on? What has been the worst?
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?
What is your favorite toy? Ever wanted to try a specific toy?
What is your view on sex? Meaning, When/Where/ How often/
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Do you like it when they show and tell you what they want?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
What have you learned about yourself that you did not before this?
Would you ever want to be woken up with oral and/or intercourse?
Escort/Client Job Applicant/Hiring Manager
19- What’s your favorite fairytale? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
49~ How many times have you been married? Why did they end?
Prisoner/Prison Guard Landlord/Tenant
29~ What are some things that turn you off? What is your biggest turn off?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
15- What bad habit do you wish you could quit? Do you have any addictions?
11- How about if they like a certain sports team? 12-How about drinking too much?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
6- Do you have dreams? Can you remember them? What do you usually dream about?
52~ What are your hobbies?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
4- For a pet, Cat, dog or other?
19- Do/have you smoked? What do you prefer? How often?
18~ Who/when was your first “crush”?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Any that are a turn off?
70~ Would/do you have/like anal sex?
You know that I will be 100% truthful, so ask.
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
9- If you could have three wishes, what would they be? Why?
What was the longest? What was the shortest?
65~ Describe the best orgasm you’ve ever had? 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.
21- What's your favorite way to spend a weekend or time off?
The Ice Breaker Questions
Will you kiss after your partner has gone down on you? Swallow or spit semen?
How about if they talk dirty and/or call you names?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
51~ Are you willing to play adult games with your partner?
9- What’s your favorite season and why? What’s your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
18- How often do you drink alcohol? What is your favorite drink?
7-What do I do in bed that drives you wild? How about, what turns you off?
14- What's your favorite dessert? Do you a least favorite?
Would you mind if your partner watched it? How about together vs alone?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Teacher/Student Stranger/One Night Stand
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Do you think this brought you closer together?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Would you allow me to clean every part of your body with my soapy hands and fingers?
84~ How do you feel about reading/listening to adult stories?
52~ Are you willing to make “those types” of bets with your partner?