What is the most interesting question you can ask to get to know someone?
11.06.2025 13:28
Repairman/Lonely Wife Virgin/Experienced
10~ How many dates are necessary before you to have sex with someone?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
11- What's your favorite restaurant? What’s your least favorite?
9- If you could have three wishes, what would they be? Why?
What happens when you get sick in a country with universal healthcare? What's the process like?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How about if they talk dirty and/or call you names?
10- What is your favorite family tradition? What’s your least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
24~ What are your expectations in a relationship? (I know a very big question, take your time)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Mysterious sphere named Teleios found floating in the Milky Way - Earth.com
27- What was/ is nickname? Does it have a meaning behind it?
71~ Would you give your partner a hand or foot job? Would you receive one?
I would allow you to do it… What would you do to me?
WWDC 2025: iOS 26 Rumored Features - MacRumors
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If yes, what?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Why do some men love sucking cocks?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
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?
37- Do you like your name? If you could change it, what would you change it too?
15~ Have you ever been “in love”? Who? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
25~ How do you feel about PDA? (Public Display of Affection)
Why do men love to stink/being smelly?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
What do you dislike about me? I asked you to be 100% honest.
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Nurse/Patient Celebrity/Fan
34- Ever been to a concert? What was your favorite? Who would you like to see?
What is your view on sex? Meaning, When/Where/ How often/
What are some creepy bestiality-promoting questions obviously asked for sexual gratification?
What have you learned about yourself that you did not before this?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Is the media protecting Kamala Harris?
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?
What would you say to prove to yourself that it was really you?
21~ What was the best date you ever went on? What has been the worst?
Do foreign workers face discrimination in Canada?
52~ Are you willing to make “those types” of bets with your partner?
53~ How much can you tell me about the one thing you are most passionate about?
Teacher/Student Stranger/One Night Stand
Jason Sudeikis Pays Tribute To His Late Uncle George Wendt: “I Love Him Dearly” - Deadline
42~ What’s your biggest regret in life?
What is your favorite position? Why?
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
*** Questions about Relationships/Past ***
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
*** Questions About Me ***
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
If NO, would you ever have one? Would it be with 2 men or 2 women?
14- What is an embarrassing moment in your life? How about your most embarrassing?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
44~ Care to share something about yourself that no one else knows about you?
81~ Do you have any kinks and/or fetishes?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Do you think this brought you closer together?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
48~ Have you ever paid or been paid for sex?
65~ Describe the best orgasm you’ve ever had? Care to share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Any that are a turn off?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
32- What's your greatest talent? Can I see it right now?
Do you like it when they show and tell you what they want?
Over time has your thoughts on sex changed?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
18- How often do you drink alcohol? What is your favorite drink?
Escort/Client Job Applicant/Hiring Manager
*** Random Questions ***
Master/Slave Boss/Maid
48~ Do you have any siblings? Are you close to your family?
2- What’s your favorite color? Do you a least favorite?
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…
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
51~ Are you willing to play adult games with your partner?
Would you allow me to clean every part of your body with my soapy hands and fingers?
36- Do you play video games? What is your favorite? Do you a least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Please share Did you stop?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Family Relation Age Play
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Do you like the “69” position? Do you prefer to be on top or bottom?
Would you read them together?
19- Do/have you smoked? What do you prefer? How often?
Get this wrong and this could mean the end… :-) some funny, some not…
*** What’s Your Favorite…? ***
4- For a pet, Cat, dog or other?
What have you learned about me that was new and/or surprising?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
17- What’s your favorite holiday? What’s your least favorite?
39~ What are your love languages?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
15- What bad habit do you wish you could quit? Do you have any addictions?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you have a favorite? Is it ok if your partner does?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Does the thought excite you? Care to share?
29~ What are some things that turn you off? What is your biggest turn off?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Any that are a turn off?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
34~ Do you like the lights on or off during sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
22- What is your favorite childhood memory? What is your least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
60~ How important is oral sex? Do you like receiving? Do you like giving?
3- What’s your favorite smell? Do you a least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
If you win, what will you make them do?
That one or two things that made you go hmmmm, OMG or wow!
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
50~ How many children do you have? What are their ages?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Will you cheat again? How can, you be sure? Define what cheating is to you.
The Ice Breaker Questions
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,
28~ What are some things that turn on? What is your biggest turn on?
Prisoner/Prison Guard Landlord/Tenant
14- What's your favorite dessert? Do you a least favorite?
10- List 5 of your top pet peeves.
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
19- What’s your favorite fairytale? What’s your least favorite?
52~ What are your hobbies?
1- What was your first impression of me? Has it changed?
30~ What's something unexpected that turns you on?
7- What if a person smells a certain way? 8- How about smoking?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
11~ Have you ever been caught by your parents or children or others while having sex?
*** Deal Breaker Questions ***
13- What is the craziest/scariest thing you've ever done?
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)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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…
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
(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…)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
76~ Have you had a threesome? Care to Share?
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?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
1- What’s your favorite animal? Do you a least favorite?
82~ Do you have any fantasies involving Role-Playing?
84~ How do you feel about reading/listening to adult stories?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
How many partners have you had oral sex with? Who? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
47~ What would be your dream job and why?
19~ Who/when was your first “heartbreak”?
12- What is the weirdest thing you've ever eaten?
8- What are your thoughts on politics?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
70~ Would/do you have/like anal sex?
* Give a rating for each one (0-100)
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?
What was the longest? What was the shortest?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
51~ What tends to bring a smile to your face?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
12- What’s your favorite food? What’s your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
If you say it, I will stop, and we can talk about it when you are ready.
How old are you? Male or Female?
58~ Have you ever taken Nude or Hard-core photos and/or videos? 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?
92~ Have you ever had or have an STD? How many? What was it?
How many times do you think you have “made love”?
28- What are some things that people do that irritate you?
31- If given a chance to be immortal, would you take it? Why?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
11- List at least 5 things on your bucket list. Have you done any of them already?
Model/Photographer Police/Criminal
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
33- Beach or Mountains? Or is there another place to like better?
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?
40~ What’s the weirdest place you’ve ever had sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
13- What’s your favorite drink? What’s your least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
67~ Do you like it when your partner moans and/or is vocal during sex?
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?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
89~ Do you like taking showers together?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Have you ever? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
How well do you know me? And some of your thoughts about me
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
83~ How do you feel about Porn?
1~ How old were you when you had your first kiss? Who? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
6- Do you have dreams? Can you remember them? What do you usually dream about?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
49~ How many times have you been married? Why did they end?
13~ Is there a difference between, making love, having sex, and fucking?
Do you watch it? What is your favorite?
36~ What is your favorite time of day to have sex/make love?
Doctor/Nurse Stripper/Client
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
7-What do I do in bed that drives you wild? How about, what turns you off?
5~ When you first started having sex, was it what you thought it would be?
Nothing too Serious
You know that I will be 100% truthful, so ask.
22- Do you have any birth marks? How about scars? Care to share how you got them?
20- What’s your favorite candy? What’s your least favorite?
62~ Have you used adult toys?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
61~ How willing would you be to try new sexual positions?
21- What's your favorite way to spend a weekend or time off?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Would you mind if your partner watched it? How about together vs alone?
9- Is there something you’ve always wanted to ask me but you’re afraid?
15- What's your favorite saying? What word or phrase is your least favorite?
Would /have you ever given your partner a lap dance and Striptease?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
26~ What side of the bed do you sleep on?
17- Have you ever done drugs? Which ones? How often?
29- How superstitious are you?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
What is your favorite toy? Ever wanted to try a specific toy?
80~ Share your top three fantasies/desires. (Be detailed) 😊
23- What is your dream job? What was it as a child?
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
18~ Who/when was your first “crush”?
3- Should Pluto still be considered a planet? 4- How about smoking?
11- How about if they like a certain sports team? 12-How about drinking too much?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
13- How about having a certain hair cut/style?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Can you Deep Throat? Do you like the taste of yourself?
3- What Superhero or Superpower would you want to be/have?
38~ Share your most embarrassing sexual memory?