What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 10:40
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
3- What Superhero or Superpower would you want to be/have?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Which Shakespeare words have completely changed meaning in modern English?
11- List at least 5 things on your bucket list. Have you done any of them already?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
19- What’s your favorite fairytale? What’s your least favorite?
What is the gayest experience you have seen in prison?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
48~ Have you ever paid or been paid for sex?
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?
How many partners have you had oral sex with? Who? Care to Share?
30~ What's something unexpected that turns you on?
25~ How do you feel about PDA? (Public Display of Affection)
11- How about if they like a certain sports team? 12-How about drinking too much?
18- How often do you drink alcohol? What is your favorite drink?
32- What's your greatest talent? Can I see it right now?
Trump’s budget puts Huntsville-made spacecraft on the chopping block - AL.com
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
42~ What’s your biggest regret in life?
Mario Kart World Coins Don't Function As You'd Expect, New Evidence Suggests - GameSpot
Over time has your thoughts on sex changed?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
6- Do you have dreams? Can you remember them? What do you usually dream about?
How do legitimate BPO companies find and secure clients without using social media?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
10~ How many dates are necessary before you to have sex with someone?
Doctor/Nurse Stripper/Client
What is the best skin care routine product for oily skin?
9- If you could have three wishes, what would they be? Why?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Would you mind if your partner watched it? How about together vs alone?
The One Food Registered Dietitians Say Isn’t as Healthy as Most People Think - Yahoo
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
If you win, what will you make them do?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
15- What's your favorite saying? What word or phrase is your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Has anyone ever participated in a gang bang and what was it like?
If you say it, I will stop, and we can talk about it when you are ready.
What is your favorite position? Why?
5~ When you first started having sex, was it what you thought it would be?
What's it like to have an IQ of 140 to 170? Do people notice you're different?
(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…)
14- What is an embarrassing moment in your life? How about your most embarrassing?
Any that are a turn off?
What are some good romantic novels?
28- What are some things that people do that irritate you?
29~ What are some things that turn you off? What is your biggest turn off?
3- What’s your favorite smell? Do you a least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
15~ Have you ever been “in love”? Who? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
How about if they talk dirty and/or call you names?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
The Ice Breaker Questions
7- What if a person smells a certain way? 8- How about smoking?
80~ Share your top three fantasies/desires. (Be detailed) 😊
33- Beach or Mountains? Or is there another place to like better?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Master/Slave Boss/Maid
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
11- What's your favorite restaurant? What’s your least favorite?
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?
47~ What would be your dream job and why?
1- What was your first impression of me? Has it changed?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
44~ Care to share something about yourself that no one else knows about you?
Would you ever want to be woken up with oral and/or intercourse?
8- What are your thoughts on politics?
*** Deal Breaker Questions ***
83~ How do you feel about Porn?
4- For a pet, Cat, dog or other?
12- What’s your favorite food? What’s your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
92~ Have you ever had or have an STD? How many? What was it?
1- What’s your favorite animal? Do you a least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
If yes, what?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Any that are a turn off?
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?
How many times do you think you have “made love”?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
14- What's your favorite dessert? Do you a least favorite?
What is your view on sex? Meaning, When/Where/ How often/
52~ Are you willing to make “those types” of bets with your partner?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Can you Deep Throat? Do you like the taste of yourself?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
33- If you could visit any time period, when would you pick? Please explain why?
76~ Have you had a threesome? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
26~ What side of the bed do you sleep on?
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?
13- What is the craziest/scariest thing you've ever done?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
61~ How willing would you be to try new sexual positions?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
53~ How much can you tell me about the one thing you are most passionate about?
Family Relation Age Play
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
That one or two things that made you go hmmmm, OMG or wow!
22- Do you have any birth marks? How about scars? Care to share how you got them?
84~ How do you feel about reading/listening to adult stories?
Nothing too Serious
19- Do/have you smoked? What do you prefer? How often?
Would /have you ever given your partner a lap dance and Striptease?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
39~ What are your love languages?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
51~ What tends to bring a smile to your face?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
*** What’s Your 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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
18~ Who/when was your first “crush”?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
You know that I will be 100% truthful, so ask.
65~ Describe the best orgasm you’ve ever had? Care to share?
23- What is your dream job? What was it as a child?
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…
36- Do you play video games? What is your favorite? Do you a least favorite?
13- What’s your favorite drink? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
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)
17- What’s your favorite holiday? What’s your least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
21~ What was the best date you ever went on? What has been the worst?
34~ Do you like the lights on or off during sex?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Get this wrong and this could mean the end… :-) some funny, some not…
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
22- What is your favorite childhood memory? What is your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
7- What are your thoughts on religion? Is there an afterlife?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
19~ Who/when was your first “heartbreak”?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
48~ Do you have any siblings? Are you close to your family?
*** Questions about Relationships/Past ***
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
11~ Have you ever been caught by your parents or children or others while having sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Model/Photographer Police/Criminal
9- Is there something you’ve always wanted to ask me but you’re afraid?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
*** Questions About Me ***
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…
Would you read them together?
What have you learned about yourself that you did not before this?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
12- What is the weirdest thing you've ever eaten?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Does the thought excite you? Care to share?
89~ Do you like taking showers together?
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?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
37- Do you like your name? If you could change it, what would you change it too?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
28~ What are some things that turn on? What is your biggest turn on?
1~ How old were you when you had your first kiss? Who? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
What do you dislike about me? I asked you to be 100% honest.
27- What was/ is nickname? Does it have a meaning behind it?
3- Should Pluto still be considered a planet? 4- How about smoking?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you do it again, and would you rather 2 females or 2 males?
2- What’s your favorite color? Do you a least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
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,
49~ How many times have you been married? Why did they end?
81~ Do you have any kinks and/or fetishes?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
* Give a rating for each one (0-100)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
10- List 5 of your top pet peeves.
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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- What’s your favorite season and why? What’s your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Please share Did you stop?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Do you think this brought you closer together?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
29- How superstitious are you?
38~ Share your most embarrassing sexual memory?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
How old are you? Male or Female?
Have you ever? Care to Share?
Escort/Client Job Applicant/Hiring Manager
Do you like it when they show and tell you what they want?
Do you watch it? What is your favorite?
Do you have a favorite? Is it ok if your partner does?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What would you say to prove to yourself that it was really you?
Teacher/Student Stranger/One Night Stand
Will you cheat again? How can, you be sure? Define what cheating is to you.
20- What’s your favorite candy? What’s your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
82~ Do you have any fantasies involving Role-Playing?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Repairman/Lonely Wife Virgin/Experienced
What was the longest? What was the shortest?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
How well do you know me? And some of your thoughts about me
Do you like the “69” position? Do you prefer to be on top or bottom?
What have you learned about me that was new and/or surprising?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
Would you allow me to shave your legs? How about your pubic hair? How about shower 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.
62~ Have you used adult toys?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
*** Random Questions ***
17- Have you ever done drugs? Which ones? How often?
7-What do I do in bed that drives you wild? How about, what turns you off?
52~ What are your hobbies?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
70~ Would/do you have/like anal sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
What is your favorite toy? Ever wanted to try a specific toy?
21- What's your favorite way to spend a weekend or time off?
51~ Are you willing to play adult games with your partner?
50~ How many children do you have? What are their ages?
8- What's your favorite flavor of ice cream? Do you a least favorite?
I would allow you to do it… What would you do to me?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
10- What is your favorite family tradition? What’s your least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Nurse/Patient Celebrity/Fan
5- Have you ever been hypnotized? Would you allow yourself to be?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
13- How about having a certain hair cut/style?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?