What is the most interesting question you can ask to get to know someone?
Last Updated: 26.06.2025 02:16
2- What’s your favorite color? Do you a least favorite?
Does the thought excite you? Care to share?
Would you ever want to be woken up with oral and/or intercourse?
6- Do you have dreams? Can you remember them? What do you usually dream about?
70~ Would/do you have/like anal sex?
Prisoner/Prison Guard Landlord/Tenant
Average penis size has increased — and Ozempic could be to blame, experts say - New York Post
What’s the longest time you gone without having sex, after, having it? How much time between the others?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
What are some sex stories from your college days?
19~ Who/when was your first “heartbreak”?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
26~ What side of the bed do you sleep on?
Do you like the “69” position? Do you prefer to be on top or bottom?
Would you mind if your partner watched it? How about together vs alone?
53~ How much can you tell me about the one thing you are most passionate about?
Do very hot men ever feel attracted to an ugly woman? Why?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
9- What’s your favorite season and why? What’s your least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Moons of Uranus surprise scientists in Hubble study - Phys.org
Nurse/Patient Celebrity/Fan
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
28- What are some things that people do that irritate you?
Corbin Carroll Diagnosed With Wrist Fracture - MLB Trade Rumors
44~ Care to share something about yourself that no one else knows about you?
*** Deal Breaker Questions ***
10~ How many dates are necessary before you to have sex with someone?
Stocks to Open Flat as Trade Pact Details Awaited: Markets Wrap - Bloomberg
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
Official website of the International Federation of Sport Climbing. - ifsc climbing
17- Have you ever done drugs? Which ones? How often?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
I feel like my boyfriend doesn't love me. Why?
61~ How willing would you be to try new sexual positions?
62~ Have you used adult toys?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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?
38~ Share your most embarrassing sexual memory?
15- What bad habit do you wish you could quit? Do you have any addictions?
19- Do/have you smoked? What do you prefer? How often?
89~ Do you like taking showers together?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Will Kamala Harris rekindle the business model of sleeping your way to the top?
34~ Do you like the lights on or off during sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
48~ Do you have any siblings? Are you close to your family?
Please share Did you stop?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What is your view on sex? Meaning, When/Where/ How often/
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
8- What are your thoughts on politics?
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
13~ Is there a difference between, making love, having sex, and fucking?
18~ Who/when was your first “crush”?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
29- How superstitious are you?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7- What if a person smells a certain way? 8- How about smoking?
82~ Do you have any fantasies involving Role-Playing?
14- What is an embarrassing moment in your life? How about your most embarrassing?
65~ Describe the best orgasm you’ve ever had? Care to share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Any that are a turn off?
3- What Superhero or Superpower would you want to be/have?
12- What’s your favorite food? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Over time has your thoughts on sex changed?
51~ What tends to bring a smile to your face?
I would allow you to do it… What would you do to me?
13- What’s your favorite drink? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
If YES, was it with 2 men or 2 women? Did you enjoy it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
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,
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
* Give a rating for each one (0-100)
40~ What’s the weirdest place you’ve ever had sex?
*** Questions About Me ***
*** Questions about Relationships/Past ***
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
50~ How many children do you have? What are their ages?
What do you dislike about me? I asked you to be 100% honest.
9- Is there something you’ve always wanted to ask me but you’re afraid?
Do you watch it? What is your favorite?
That one or two things that made you go hmmmm, OMG or wow!
30~ What's something unexpected that turns you on?
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Can you Deep Throat? Do you like the taste of yourself?
33- Beach or Mountains? Or is there another place to like better?
Any that are a turn off?
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 was the most surprising thing you’ve learned about me throughout our relationship?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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…
14- What's your favorite dessert? Do you a least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
45~ How do you feel about me blindfolding you? How about blindfolding me?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
What have you learned about yourself that you did not before this?
83~ How do you feel about Porn?
52~ Are you willing to make “those types” of bets with your partner?
Have you ever? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
How many partners have you had oral sex with? Who? Care to Share?
*** What’s Your Favorite…? ***
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 about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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)
(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…)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What have you learned about me that was new and/or surprising?
Master/Slave Boss/Maid
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
15~ Have you ever been “in love”? Who? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
10- What is your favorite family tradition? What’s your least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
67~ Do you like it when your partner moans and/or is vocal during sex?
Nothing too Serious
How well do you know me? And some of your thoughts about me
23- What is your dream job? What was it as a child?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
What is your favorite toy? Ever wanted to try a specific toy?
36~ What is your favorite time of day to have sex/make love?
10- List 5 of your top pet peeves.
92~ Have you ever had or have an STD? How many? What was it?
How about if they talk dirty and/or call you names?
11- List at least 5 things on your bucket list. Have you done any of them already?
81~ Do you have any kinks and/or fetishes?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
22- What is your favorite childhood memory? What is your least favorite?
What would you say to prove to yourself that it was really you?
3- What’s your favorite smell? Do you a least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Family Relation Age Play
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
49~ How many times have you been married? Why did they end?
27- What was/ is nickname? Does it have a meaning behind it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
29~ What are some things that turn you off? What is your biggest turn off?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
92~ Everyone needs a “safe” word. What is yours?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
76~ Have you had a threesome? Care to Share?
47~ What would be your dream job and why?
How old are you? Male or Female?
Would you do it again, and would you rather 2 females or 2 males?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
Would you read them together?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
If you win, what will you make them do?
34- Ever been to a concert? What was your favorite? Who would you like to see?
If NO, would you ever have one? Would it be with 2 men or 2 women?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
21- What's your favorite way to spend a weekend or time off?
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?
18- How often do you drink alcohol? What is your favorite drink?
4- For a pet, Cat, dog or other?
37- Do you like your name? If you could change it, what would you change it too?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
48~ Have you ever paid or been paid for sex?
Escort/Client Job Applicant/Hiring Manager
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
13- How about having a certain hair cut/style?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Do you think this brought you closer together?
1- What’s your favorite animal? Do you a least favorite?
52~ What are your hobbies?
Do you have a favorite? Is it ok if your partner does?
7- What’s your favorite book? Do you have a favorite genre? 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…
39~ What are your love languages?
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?
19- What’s your favorite fairytale? What’s your least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
36- Do you play video games? What is your favorite? Do you a least favorite?
Would /have you ever given your partner a lap dance and Striptease?
51~ Are you willing to play adult games with your partner?
12- What is the weirdest thing you've ever eaten?
*** Random Questions ***
The Ice Breaker Questions
22~ What is the best pickup line anyone has ever used on you? What was the worst?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
13- What is the craziest/scariest thing you've ever done?
28~ What are some things that turn on? What is your biggest turn on?
32- What's your greatest talent? Can I see it right now?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
71~ Would you give your partner a hand or foot job? Would you receive one?
You know that I will be 100% truthful, so ask.
Would you allow me to clean every part of your body with my soapy hands and fingers?
21~ What was the best date you ever went on? What has been the worst?
22- Do you have any birth marks? How about scars? Care to share how you got them?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Teacher/Student Stranger/One Night Stand
9- If you could have three wishes, what would they be? Why?
Do you like it when they show and tell you what they want?
17- What’s your favorite holiday? What’s your least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
7-What do I do in bed that drives you wild? How about, what turns you off?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
33- If you could visit any time period, when would you pick? Please explain why?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
11~ Have you ever been caught by your parents or children or others while having sex?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Model/Photographer Police/Criminal
11- How about if they like a certain sports team? 12-How about drinking too much?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
1- What was your first impression of me? Has it changed?
11- What's your favorite restaurant? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
20- What’s your favorite candy? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
7- What are your thoughts on religion? Is there an afterlife?
If you say it, I will stop, and we can talk about it when you are ready.
42~ What’s your biggest regret in life?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
1~ How old were you when you had your first kiss? Who? Care to Share?
How many times do you think you have “made love”?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What is your favorite position? Why?
If yes, what?
Repairman/Lonely Wife Virgin/Experienced
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
9~ How many times over your lifetime do you think you have had sex so far?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What was the longest? What was the shortest?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Doctor/Nurse Stripper/Client
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?