What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 04:18
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?
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,
Can you Deep Throat? Do you like the taste of yourself?
Why should you never do drugs? Will this story absolutely shock you?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
51~ Are you willing to play adult games with your partner?
62~ Have you used adult toys?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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 to Cut Your Biological Age by Up to 16 Years: Make This Tweak to Your Daily Walk - Inc.com
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
29- How superstitious are you?
Why do unattractive men assume that a pretty woman like me want them?
5~ When you first started having sex, was it what you thought it would be?
92~ Everyone needs a “safe” word. What is yours?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Apple’s Upgrades to CarPlay, iPad and Vision Pro Outshine Liquid Glass - Bloomberg.com
If NO, would you ever have one? Would it be with 2 men or 2 women?
89~ Do you like taking showers together?
If YES, was it with 2 men or 2 women? Did you enjoy it?
51~ What tends to bring a smile to your face?
13- What’s your favorite drink? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
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?
18- How often do you drink alcohol? What is your favorite drink?
3- What Superhero or Superpower would you want to be/have?
What is the XXX XXX Keerna Kappor video?
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?
Do you think this brought you closer together?
Why aren't you a Trump supporter?
11- List at least 5 things on your bucket list. Have you done any of them already?
Do you like it when they show and tell you what they want?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What are James Potter's flaws?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Family Relation Age Play
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
When will dating stop being so hard for Gen Z?
Repairman/Lonely Wife Virgin/Experienced
18- What’s your favorite way to relax after a long day? What’s your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Would you let your partner cheat on you every now and again?
53~ How much can you tell me about the one thing you are most passionate about?
14- What is an embarrassing moment in your life? How about your most embarrassing?
49~ How many times have you been married? Why did they end?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
39~ What are your love languages?
How do you feel about Donald Trump signing an executive order that says there are only two genders?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
65~ Describe the best orgasm you’ve ever had? Care to share?
3- What’s your favorite smell? Do you a least favorite?
Does the thought excite you? Care to share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
How many times do you think you have “made love”?
71~ Would you give your partner a hand or foot job? Would you receive one?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
44~ Care to share something about yourself that no one else knows about you?
19~ Who/when was your first “heartbreak”?
Over time has your thoughts on sex changed?
12- What is the weirdest thing you've ever eaten?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
48~ Have you ever paid or been paid for sex?
29~ What are some things that turn you off? What is your biggest turn off?
15- What's your favorite saying? What word or phrase is your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
13~ Is there a difference between, making love, having sex, and fucking?
Teacher/Student Stranger/One Night Stand
Would you mind if your partner watched it? How about together vs alone?
Prisoner/Prison Guard Landlord/Tenant
45~ How do you feel about me blindfolding you? How about blindfolding me?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
*** What’s Your 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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
32- What's your greatest talent? Can I see it right now?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Would you allow me to clean every part of your body with my soapy hands and fingers?
33- If you could visit any time period, when would you pick? Please explain why?
What is your favorite toy? Ever wanted to try a specific toy?
Do you watch it? What is your favorite?
17- What’s your favorite holiday? What’s your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Would /have you ever given your partner a lap dance and Striptease?
(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…)
Would you read them together?
What have you learned about yourself that you did not before this?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Escort/Client Job Applicant/Hiring Manager
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
I would allow you to do it… What would you do to me?
*** Deal Breaker Questions ***
How well do you know me? And some of your thoughts about me
70~ Would/do you have/like anal sex?
10~ How many dates are necessary before you to have sex with someone?
7- What are your thoughts on religion? Is there an afterlife?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
The Ice Breaker Questions
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?
9~ How many times over your lifetime do you think you have had sex so far?
Would you do it again, and would you rather 2 females or 2 males?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
9- What’s your favorite season and why? 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…
If yes, what?
What do you dislike about me? I asked you to be 100% honest.
81~ Do you have any kinks and/or fetishes?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Have you ever? Care to Share?
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?
22- What is your favorite childhood memory? What is your least favorite?
48~ Do you have any siblings? Are you close to your family?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
36- Do you play video games? What is your favorite? Do you a least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
30~ What's something unexpected that turns you on?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
8- What's your favorite flavor of ice cream? Do you a least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
19- Do/have you smoked? What do you prefer? How often?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
4- For a pet, Cat, dog or other?
17- Have you ever done drugs? Which ones? How often?
8- What are your thoughts on politics?
10- What is your favorite family tradition? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Nurse/Patient Celebrity/Fan
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What have you learned about me that was new and/or surprising?
Please share Did you stop?
* Give a rating for each one (0-100)
34~ Do you like the lights on or off during sex?
19- What’s your favorite fairytale? What’s your least favorite?
61~ How willing would you be to try new sexual positions?
Model/Photographer Police/Criminal
Any that are a turn off?
1- What was your first impression of me? Has it changed?
What is your favorite position? Why?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
26~ What side of the bed do you sleep on?
11- What's your favorite restaurant? What’s your least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
31- If given a chance to be immortal, would you take it? Why?
18~ Who/when was your first “crush”?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
5- Have you ever been hypnotized? Would you allow yourself to be?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
9- If you could have three wishes, what would they be? Why?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
76~ Have you had a threesome? Care to Share?
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?
67~ Do you like it when your partner moans and/or is vocal during sex?
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
7- What if a person smells a certain way? 8- How about smoking?
If you say it, I will stop, and we can talk about it when you are ready.
You know that I will be 100% truthful, so ask.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
23- What is your dream job? What was it as a child?
How many partners have you had oral sex with? Who? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
92~ Have you ever had or have an STD? How many? What was it?
50~ How many children do you have? What are their ages?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What would you say to prove to yourself that it was really you?
47~ What would be your dream job and why?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
7-What do I do in bed that drives you wild? How about, what turns you off?
Do you have a favorite? Is it ok if your partner does?
25~ How do you feel about PDA? (Public Display of Affection)
33- Beach or Mountains? Or is there another place to like better?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
42~ What’s your biggest regret in life?
10- List 5 of your top pet peeves.
20- What’s your favorite candy? What’s your least favorite?
13- What is the craziest/scariest thing you've ever done?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Master/Slave Boss/Maid
83~ How do you feel about Porn?
Doctor/Nurse Stripper/Client
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…
*** Random Questions ***
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
28~ What are some things that turn on? What is your biggest turn on?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
*** Questions about Relationships/Past ***
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 kiss after your partner has gone down on you? Swallow or spit semen?
21- What's your favorite way to spend a weekend or time off?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
12- What’s your favorite food? 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 was the longest? What was the shortest?
52~ Are you willing to make “those types” of bets with your partner?
1- What’s your favorite animal? Do you a least favorite?
84~ How do you feel about reading/listening to adult stories?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
14- What's your favorite dessert? Do you a least favorite?
15~ Have you ever been “in love”? Who? 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)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
82~ Do you have any fantasies involving Role-Playing?
If you win, what will you make them do?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
How about if they talk dirty and/or call you names?
80~ Share your top three fantasies/desires. (Be detailed) 😊
38~ Share your most embarrassing sexual memory?
How old are you? Male or Female?
2- What’s your favorite color? Do you a least favorite?
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
28- What are some things that people do that irritate you?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
13- How about having a certain hair cut/style?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
36~ What is your favorite time of day to have sex/make love?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
What is your view on sex? Meaning, When/Where/ How often/
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
11~ Have you ever been caught by your parents or children or others while having sex?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
That one or two things that made you go hmmmm, OMG or wow!
Would you ever want to be woken up with oral and/or intercourse?
Any that are a turn off?
40~ What’s the weirdest place you’ve ever had sex?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** Questions About Me ***
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Nothing too Serious
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
52~ What are your hobbies?