What is the most interesting question you can ask to get to know someone?
10.06.2025 08:34
42~ What’s your biggest regret in life?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Escort/Client Job Applicant/Hiring Manager
9- If you could have three wishes, what would they be? Why?
How well do you know me? And some of your thoughts about me
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
35 Father’s Day Gifts For Anyone Who Still Doesn’t Know What The Heck To Get Their Dad - BuzzFeed
Do you have a favorite? Is it ok if your partner does?
Would you do it again, and would you rather 2 females or 2 males?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
How do you have intercourse with a girl who can remember you for a long time?
29- How superstitious are you?
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?
Do you watch it? What is your favorite?
51~ What tends to bring a smile to your face?
13- What’s your favorite drink? What’s your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Would you let your partner cheat on you every now and again?
8- What are your thoughts on politics?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Over time has your thoughts on sex changed?
The mystery rise of lung cancer in non-smokers - BBC
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
61~ How willing would you be to try new sexual positions?
34~ Do you like the lights on or off during sex?
Why do men love boobs (irrespective of big or small)?
*** What’s Your Favorite…? ***
39~ What are your love languages?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would you read them together?
7- What are your thoughts on religion? Is there an afterlife?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
What have you learned about me that was new and/or surprising?
71~ Would you give your partner a hand or foot job? Would you receive one?
How many times do you think you have “made love”?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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…
Jobs report shifts Fed interest rate forecasts - TheStreet
Please share Did you stop?
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?
*** Questions About Me ***
What kind of lights would you like to use for your home decor?
48~ Do you have any siblings? Are you close to your family?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Police take back statement dismissing hate crime in gay actor’s killing - The Washington Post
18~ Who/when was your first “crush”?
36~ What is your favorite time of day to have sex/make love?
8- What's your favorite flavor of ice cream? Do you a least favorite?
5~ When you first started having sex, was it what you thought it would be?
81~ Do you have any kinks and/or fetishes?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Master/Slave Boss/Maid
Doctor/Nurse Stripper/Client
48~ Have you ever paid or been paid for sex?
38~ Share your most embarrassing sexual memory?
50~ How many children do you have? What are their ages?
80~ Share your top three fantasies/desires. (Be detailed) 😊
25~ How do you feel about PDA? (Public Display of Affection)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
If you win, what will you make them do?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What is your view on sex? Meaning, When/Where/ How often/
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
15~ Have you ever been “in love”? Who? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
If NO, would you ever have one? Would it be with 2 men or 2 women?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
9~ How many times over your lifetime do you think you have had sex so far?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
65~ Describe the best orgasm you’ve ever had? Care to share?
19~ Who/when was your first “heartbreak”?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
28~ What are some things that turn on? What is your biggest turn on?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Any that are a turn 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?
84~ How do you feel about reading/listening to adult stories?
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?
Can you Deep Throat? Do you like the taste of yourself?
33- Beach or Mountains? Or is there another place to like better?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
5- Have you ever been hypnotized? Would you allow yourself to be?
32- What's your greatest talent? Can I see it right now?
*** Questions about Relationships/Past ***
6- Do you have dreams? Can you remember them? What do you usually dream about?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
52~ What are your hobbies?
37- Do you like your name? If you could change it, what would you change it too?
Do you think this brought you closer together?
9- Is there something you’ve always wanted to ask me but you’re afraid?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
29~ What are some things that turn you off? What is your biggest turn off?
4- For a pet, Cat, dog or other?
What would you say to prove to yourself that it was really you?
53~ How much can you tell me about the one thing you are most passionate about?
How many partners have you had oral sex with? Who? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
13- What is the craziest/scariest thing you've ever done?
How old are you? Male or Female?
60~ How important is oral sex? Do you like receiving? Do you like giving?
21~ What was the best date you ever went on? What has been the worst?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Get this wrong and this could mean the end… :-) some funny, some not…
Repairman/Lonely Wife Virgin/Experienced
22- What is your favorite childhood memory? What is your least 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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
You know that I will be 100% truthful, so ask.
14- What's your favorite dessert? Do you a least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Nothing too Serious
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
49~ How many times have you been married? Why did they end?
33- If you could visit any time period, when would you pick? Please explain why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
92~ Everyone needs a “safe” word. What is yours?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Would you ever want to be woken up with oral and/or intercourse?
If yes, what?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Prisoner/Prison Guard Landlord/Tenant
Family Relation Age Play
51~ Are you willing to play adult games with your partner?
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)
What have you learned about yourself that you did not before this?
15- What bad habit do you wish you could quit? Do you have any addictions?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Would /have you ever given your partner a lap dance and Striptease?
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?
83~ How do you feel about Porn?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Do you like it when they show and tell you what they want?
15- What's your favorite saying? What word or phrase is your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Nurse/Patient Celebrity/Fan
7-What do I do in bed that drives you wild? How about, what turns you off?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
*** Deal Breaker Questions ***
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
17- Have you ever done drugs? Which ones? How often?
9- What’s your favorite season and why? What’s your least favorite?
11- What's your favorite restaurant? What’s your least favorite?
17- What’s your favorite holiday? What’s your least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
11- List at least 5 things on your bucket list. Have you done any of them already?
2- What’s your favorite color? Do you a least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
How about if they talk dirty and/or call you names?
27- What was/ is nickname? Does it have a meaning behind it?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
67~ Do you like it when your partner moans and/or is vocal during sex?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
1- What’s your favorite animal? Do you a least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
* Give a rating for each one (0-100)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Does the thought excite you? Care to share?
11- How about if they like a certain sports team? 12-How about drinking too much?
3- What’s your favorite smell? Do you a least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
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?
19- What’s your favorite fairytale? What’s your least favorite?
10~ How many dates are necessary before you to have sex with someone?
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…
28- What are some things that people do that irritate you?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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’s the longest time you gone without having sex, after, having it? How much time between the others?
23- What is your dream job? What was it as a child?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
3- What Superhero or Superpower would you want to be/have?
The Ice Breaker Questions
Do you shave/trim your pubic hair? For you guys do you shave your balls?
76~ Have you had a threesome? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
10- What is your favorite family tradition? What’s your least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
12- What’s your favorite food? What’s your least favorite?
7- What if a person smells a certain way? 8- How about smoking?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What was the longest? What was the shortest?
What is your favorite toy? Ever wanted to try a specific toy?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
62~ Have you used adult toys?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
*** Random Questions ***
1- What was your first impression of me? Has it changed?
30~ What's something unexpected that turns you on?
13~ Is there a difference between, making love, having sex, and fucking?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
If you say it, I will stop, and we can talk about it when you are ready.
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Would you mind if your partner watched it? How about together vs alone?
70~ Would/do you have/like anal sex?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
40~ What’s the weirdest place you’ve ever had sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What is your favorite position? Why?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
20- What’s your favorite candy? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
Any that are a turn off?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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,
I would allow you to do it… What would you do to me?
12- What is the weirdest thing you've ever eaten?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
13- How about having a certain hair cut/style?
26~ What side of the bed do you sleep on?
Have you ever? Care to Share?
89~ Do you like taking showers together?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
That one or two things that made you go hmmmm, OMG or wow!
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Would you allow me to clean every part of your body with my soapy hands and fingers?
92~ Have you ever had or have an STD? How many? What was it?
Teacher/Student Stranger/One Night Stand
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What do you dislike about me? I asked you to be 100% honest.
47~ What would be your dream job and why?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
31- If given a chance to be immortal, would you take it? Why?
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.
Model/Photographer Police/Criminal
52~ Are you willing to make “those types” of bets with your partner?
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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
34- Ever been to a concert? What was your favorite? Who would you like to see?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
1~ How old were you when you had your first kiss? Who? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
7~ How many times in one day have you had sex? Who/When/Where? 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…)