What is the most interesting question you can ask to get to know someone?
08.06.2025 02:53
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?
33- If you could visit any time period, when would you pick? Please explain why?
12- What’s your favorite food? What’s your least favorite?
What is the best case of “You just picked a fight with the wrong person” that you've witnessed?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Do you like it when they show and tell you what they want?
10- What is your favorite family tradition? What’s your least favorite?
Please share Did you stop?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Do you watch it? What is your favorite?
'Orthorexia' Is More And More Common. Here's What You Should Know About It. - HuffPost
Any that are a turn off?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Why do narcissists devour so much sugar (candy, ice cream, donuts, etc., in huge amounts at a time)?
Model/Photographer Police/Criminal
51~ Are you willing to play adult games with your partner?
36~ What is your favorite time of day to have sex/make love?
7- What if a person smells a certain way? 8- How about smoking?
45~ How do you feel about me blindfolding you? How about blindfolding me?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Scientists are experimenting with a completely new approach to combat human aging - Earth.com
49~ If you could, would you want to be the opposite sex for a day, week, or year?
15- What bad habit do you wish you could quit? Do you have any addictions?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
40~ What’s the weirdest place you’ve ever had sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Why would my husband cheat on me with an ugly fat woman?
Over time has your thoughts on sex changed?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Do you have any problem dating a younger man?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
26~ What side of the bed do you sleep on?
*** What’s Your Favorite…? ***
Let's Weigh The Pros And Cons Of Inviting Larry David To Your Wedding - OutKick
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
34- Ever been to a concert? What was your favorite? Who would you like to see?
What Wilson said about Logan Gilbert’s second rehab start - Seattle Sports
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Master/Slave Boss/Maid
81~ Do you have any kinks and/or fetishes?
What do you typically do while on meth?
47~ What would be your dream job and why?
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)
50~ How many children do you have? What are their ages?
21~ What was the best date you ever went on? What has been the worst?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
* Give a rating for each one (0-100)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
9~ How many times over your lifetime do you think you have had sex so far?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
4- For a pet, Cat, dog or other?
Nurse/Patient Celebrity/Fan
8- What's your favorite flavor of ice cream? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
What have you learned about me that was new and/or surprising?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Would you do it again, and would you rather 2 females or 2 males?
14- What's your favorite dessert? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Get this wrong and this could mean the end… :-) some funny, some not…
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
(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…)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
42~ What’s your biggest regret in life?
70~ Would/do you have/like anal sex?
Any that are a turn off?
Doctor/Nurse Stripper/Client
That one or two things that made you go hmmmm, OMG or wow!
28- What are some things that people do that irritate you?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
*** Deal Breaker Questions ***
29- How superstitious are you?
52~ What are your hobbies?
What would you say to prove to yourself that it was really you?
18~ Who/when was your first “crush”?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What is your favorite toy? Ever wanted to try a specific toy?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
32- What's your greatest talent? Can I see it right now?
33- Beach or Mountains? Or is there another place to like better?
65~ Describe the best orgasm you’ve ever had? Care to share?
76~ Have you had a threesome? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
52~ Are you willing to make “those types” of bets with your partner?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Teacher/Student Stranger/One Night Stand
11~ Have you ever been caught by your parents or children or others while having sex?
1~ How old were you when you had your first kiss? Who? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Can you Deep Throat? Do you like the taste of yourself?
9- If you could have three wishes, what would they be? Why?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
34~ Do you like the lights on or off during sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
12- What is the weirdest thing you've ever eaten?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
The Ice Breaker Questions
Have you ever? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?
39~ What are your love languages?
20- What’s your favorite candy? What’s your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
1- What’s your favorite animal? Do you a least favorite?
If you win, what will you make them do?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Would you allow me to clean every part of your body with my soapy hands and fingers?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
13- What’s your favorite drink? What’s your least favorite?
28~ What are some things that turn on? What is your biggest turn on?
10~ How many dates are necessary before you to have sex with someone?
Would /have you ever given your partner a lap dance and Striptease?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Prisoner/Prison Guard Landlord/Tenant
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
*** Random Questions ***
*** Questions about Relationships/Past ***
What is your view on sex? Meaning, When/Where/ How often/
What do you dislike about me? I asked you to be 100% honest.
37- Do you like your name? If you could change it, what would you change it too?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
6- Do you have dreams? Can you remember them? What do you usually dream about?
48~ Do you have any siblings? Are you close to your family?
13- What is the craziest/scariest thing you've ever done?
25~ How do you feel about PDA? (Public Display of Affection)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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…
3- Should Pluto still be considered a planet? 4- How about smoking?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
61~ How willing would you be to try new sexual positions?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
53~ How much can you tell me about the one thing you are most passionate about?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Do you have a favorite? Is it ok if your partner does?
11- How about if they like a certain sports team? 12-How about drinking too much?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
How many times do you think you have “made love”?
11- List at least 5 things on your bucket list. Have you done any of them already?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
If you say it, I will stop, and we can talk about it when you are ready.
What is your favorite position? Why?
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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Family Relation Age Play
29~ What are some things that turn you off? What is your biggest turn off?
17- What’s your favorite holiday? What’s your least favorite?
How well do you know me? And some of your thoughts about me
Would you mind if your partner watched it? How about together vs alone?
11- What's your favorite restaurant? What’s your least favorite?
2- What’s your favorite color? Do you a least favorite?
17- Have you ever done drugs? Which ones? How often?
How about if they talk dirty and/or call you names?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Would you read them together?
62~ Have you used adult toys?
What have you learned about yourself that you did not before this?
22- Do you have any birth marks? How about scars? Care to share how you got them?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
83~ How do you feel about Porn?
36- Do you play video games? What is your favorite? Do you a least favorite?
How many partners have you had oral sex with? Who? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
How old are you? Male or Female?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
13~ Is there a difference between, making love, having sex, and fucking?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If YES, was it with 2 men or 2 women? Did you enjoy it?
67~ Do you like it when your partner moans and/or is vocal during sex?
49~ How many times have you been married? Why did they end?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
84~ How do you feel about reading/listening to adult stories?
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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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,
41~ Are there moments in your past that you would want to change? Please share 3 of them.
82~ Do you have any fantasies involving Role-Playing?
If NO, would you ever have one? Would it be with 2 men or 2 women?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Escort/Client Job Applicant/Hiring Manager
1- What was your first impression of me? Has it changed?
15- What's your favorite saying? What word or phrase is your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
I would allow you to do it… What would you do to me?
92~ Everyone needs a “safe” word. What is yours?
13- How about having a certain hair cut/style?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Repairman/Lonely Wife Virgin/Experienced
60~ How important is oral sex? Do you like receiving? Do you like giving?
30~ What's something unexpected that turns you on?
Nothing too Serious
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
18- How often do you drink alcohol? What is your favorite drink?
Do you think this brought you closer together?
3- What’s your favorite smell? Do you a least favorite?
23- What is your dream job? What was it as a child?
89~ Do you like taking showers together?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
8- What are your thoughts on politics?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Does the thought excite you? 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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
You know that I will be 100% truthful, so ask.
3- What Superhero or Superpower would you want to be/have?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
38~ Share your most embarrassing sexual memory?
If yes, what?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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…
9- What’s your favorite season and why? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
22- What is your favorite childhood memory? What is your least favorite?
18- What’s your favorite way to relax after a long day? What’s your 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?
5~ When you first started having sex, was it what you thought it would be?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
*** Questions About Me ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
9- Is there something you’ve always wanted to ask me but you’re afraid?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
92~ Have you ever had or have an STD? How many? What was it?
27- What was/ is nickname? Does it have a meaning behind it?
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?
Do you like the “69” position? Do you prefer to be on top or bottom?
19~ Who/when was your first “heartbreak”?
51~ What tends to bring a smile to your face?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
10- List 5 of your top pet peeves.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
What was the longest? What was the shortest?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
44~ Care to share something about yourself that no one else knows about you?
19- Do/have you smoked? What do you prefer? How often?
71~ Would you give your partner a hand or foot job? Would you receive one?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
7-What do I do in bed that drives you wild? How about, what turns you off?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?