What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 17:36
20- What’s your favorite candy? What’s your least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
What do you dislike about me? I asked you to be 100% honest.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
What is your review of "Regent", episode 5 of Season 2 House of the Dragon?
*** What’s Your Favorite…? ***
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Has anyone ever had sex with their cousin? How did it start, and would you do it again?
Over time has your thoughts on sex changed?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
What is your daily motivation and does it work?
Prisoner/Prison Guard Landlord/Tenant
3- What’s your favorite smell? Do you a least favorite?
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)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Family Relation Age Play
Why does my sister want to have sex with me? What should I do?
That one or two things that made you go hmmmm, OMG or wow!
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.
What are the best AI recruiting tools and AI hiring software available today?
Would you do it again, and would you rather 2 females or 2 males?
*** Random Questions ***
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
New Study Finds 1 Promising Way To Keep Colon Cancer From Returning - HuffPost
71~ Would you give your partner a hand or foot job? Would you receive one?
13- What is the craziest/scariest thing you've ever done?
19- What’s your favorite fairytale? What’s your least favorite?
The comments from Jamie Dimon last week are worth repeating - Forexlive
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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
92~ Everyone needs a “safe” word. What is yours?
Facial Stimulation Clears Brain Waste and Boosts Aging Minds - Neuroscience News
9- If you could have three wishes, what would they be? Why?
How about if they talk dirty and/or call you names?
92~ Have you ever had or have an STD? How many? What was it?
What is the most craziest dream you ever had?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
36~ What is your favorite time of day to have sex/make love?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How do you stop your balls from sweating?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
33- If you could visit any time period, when would you pick? Please explain why?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Do you like it when they show and tell you what they want?
29~ What are some things that turn you off? What is your biggest turn off?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
48~ Do you have any siblings? Are you close to your family?
Do you have a favorite? Is it ok if your partner does?
Have you ever? Care to Share?
*** Questions about Relationships/Past ***
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
47~ What would be your dream job and why?
52~ What are your hobbies?
53~ How much can you tell me about the one thing you are most passionate about?
What have you learned about yourself that you did not before this?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
33- Beach or Mountains? Or is there another place to like better?
9- Is there something you’ve always wanted to ask me but you’re afraid?
You know that I will be 100% truthful, so ask.
If you say it, I will stop, and we can talk about it when you are ready.
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
65~ Describe the best orgasm you’ve ever had? Care to share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
5- Have you ever been hypnotized? Would you allow yourself to be?
14- What's your favorite dessert? Do you a least favorite?
Nurse/Patient Celebrity/Fan
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
22- What is your favorite childhood memory? What is your least favorite?
82~ Do you have any fantasies involving Role-Playing?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Escort/Client Job Applicant/Hiring Manager
15~ Have you ever been “in love”? Who? Care to Share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
28- What are some things that people do that irritate you?
70~ Would/do you have/like anal sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
12- What is the weirdest thing you've ever eaten?
Please share Did you stop?
Do you watch it? What is your favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
7- What if a person smells a certain way? 8- How about smoking?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
1- What’s your favorite animal? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
29- How superstitious are you?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
19~ Who/when was your first “heartbreak”?
31- If given a chance to be immortal, would you take it? Why?
Any that are a turn off?
19- Do/have you smoked? What do you prefer? How often?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
51~ Are you willing to play adult games with your partner?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
What was the longest? What was the shortest?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
How many times do you think you have “made love”?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What is your favorite toy? Ever wanted to try a specific toy?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Would you mind if your partner watched it? How about together vs alone?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
49~ How many times have you been married? Why did they end?
25~ How do you feel about PDA? (Public Display of Affection)
81~ Do you have any kinks and/or fetishes?
26~ What side of the bed do you sleep on?
8- What are your thoughts on politics?
11- List at least 5 things on your bucket list. Have you done any of them already?
84~ How do you feel about reading/listening to adult stories?
89~ Do you like taking showers together?
15- What bad habit do you wish you could quit? Do you have any addictions?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
61~ How willing would you be to try new sexual positions?
Get this wrong and this could mean the end… :-) some funny, some not…
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
* Give a rating for each one (0-100)
Teacher/Student Stranger/One Night Stand
What’s the longest time you gone without having sex, after, having it? How much time between the others?
1~ How old were you when you had your first kiss? Who? Care to Share?
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…
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
What is your view on sex? Meaning, When/Where/ How often/
If NO, would you ever have one? Would it be with 2 men or 2 women?
Would you allow me to clean every part of your body with my soapy hands and fingers?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Would /have you ever given your partner a lap dance and Striptease?
39~ What are your love languages?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
10~ How many dates are necessary before you to have sex with someone?
13- What’s your favorite drink? What’s your least favorite?
Does the thought excite you? Care to share?
Do you like the “69” position? Do you prefer to be on top or bottom?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How many partners have you had oral sex with? Who? Care to Share?
4- For a pet, Cat, dog or other?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
17- Have you ever done drugs? Which ones? How often?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
21~ What was the best date you ever went on? What has been the worst?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
I would allow you to do it… What would you do to me?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
32- What's your greatest talent? Can I see it right now?
18- How often do you drink alcohol? What is your favorite drink?
9~ How many times over your lifetime do you think you have had sex so far?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
11- What's your favorite restaurant? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
1- What was your first impression of me? Has it changed?
17- What’s your favorite holiday? 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?
18~ Who/when was your first “crush”?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
15- What's your favorite saying? What word or phrase is your least favorite?
How well do you know me? And some of your thoughts about me
44~ Care to share something about yourself that no one else knows about you?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
*** Questions About Me ***
Would you read them together?
Would you ever want to be woken up with oral and/or intercourse?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Do you think this brought you closer together?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
22- Do you have any birth marks? How about scars? Care to share how you got them?
40~ What’s the weirdest place you’ve ever had sex?
2- What’s your favorite color? Do you a least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What have you learned about me that was new and/or surprising?
3- What Superhero or Superpower would you want to be/have?
What would you say to prove to yourself that it was really you?
28~ What are some things that turn on? What is your biggest turn on?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Master/Slave Boss/Maid
51~ What tends to bring a smile to your face?
Model/Photographer Police/Criminal
What is your favorite position? Why?
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…
48~ Have you ever paid or been paid for sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
13- How about having a certain hair cut/style?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
45~ How do you feel about me blindfolding you? How about blindfolding me?
34~ Do you like the lights on or off during sex?
67~ Do you like it when your partner moans and/or is vocal during sex?
12- What’s your favorite food? What’s your least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
11~ Have you ever been caught by your parents or children or others while having sex?
37- Do you like your name? If you could change it, what would you change it too?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
23- What is your dream job? What was it as a child?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Any that are a turn off?
52~ Are you willing to make “those types” of bets with your partner?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Nothing too Serious
*** Deal Breaker Questions ***
41~ Are there moments in your past that you would want to change? Please share 3 of them.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
7- What are your thoughts on religion? Is there an afterlife?
Repairman/Lonely Wife Virgin/Experienced
21- What's your favorite way to spend a weekend or time off?
10- List 5 of your top pet peeves.
30~ What's something unexpected that turns you on?
62~ Have you used adult toys?
The Ice Breaker Questions
Can you Deep Throat? Do you like the taste of yourself?
(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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
34- Ever been to a concert? What was your favorite? Who would you like to see?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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?
3- Should Pluto still be considered a planet? 4- How about smoking?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
76~ Have you had a threesome? Care to Share?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
10- What is your favorite family tradition? What’s your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
Doctor/Nurse Stripper/Client
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
If you win, what will you make them do?
(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…)
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?
If yes, what?
How old are you? Male or Female?
83~ How do you feel about Porn?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
50~ How many children do you have? What are their ages?
42~ What’s your biggest regret in life?
13~ Is there a difference between, making love, having sex, and fucking?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?