What is the most interesting question you can ask to get to know someone?
08.06.2025 03:23
Teacher/Student Stranger/One Night Stand
92~ Everyone needs a “safe” word. What is yours?
29- How superstitious are you?
Swap Out The Dated Eucalyptus Decor Trend For This More Modern Option - House Digest
Nothing too Serious
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Escort/Client Job Applicant/Hiring Manager
Can I know a love story of a medical student?
Would you read them together?
14- What's your favorite dessert? Do you a least favorite?
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?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
17- Have you ever done drugs? Which ones? How often?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Why doesn’t the UK change their flag?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
13- What’s your favorite drink? What’s your least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
Random Eagles notes: Bryce Huff trade perhaps signals some confidence in Azeez Ojulari - PhillyVoice
10- What is your favorite family tradition? What’s your least favorite?
Any that are a turn off?
What is your favorite position? Why?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Doctor/Nurse Stripper/Client
21- What's your favorite way to spend a weekend or time off?
7- What are your thoughts on religion? Is there an afterlife?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
19- Do/have you smoked? What do you prefer? How often?
Do married men know when their wives are having affairs?
1- What’s your favorite animal? Do you a least favorite?
* Give a rating for each one (0-100)
44~ Care to share something about yourself that no one else knows about you?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Model/Photographer Police/Criminal
33- Beach or Mountains? Or is there another place to like better?
Get this wrong and this could mean the end… :-) some funny, some not…
81~ Do you have any kinks and/or fetishes?
31- If given a chance to be immortal, would you take it? Why?
What are tips for weight loss?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
18~ Who/when was your first “crush”?
What do you dislike about me? I asked you to be 100% honest.
Why am I sweating so much when I try to do anything?
71~ Would you give your partner a hand or foot job? Would you receive one?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
21~ What was the best date you ever went on? What has been the worst?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
7- What if a person smells a certain way? 8- How about smoking?
Over time has your thoughts on sex changed?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Would /have you ever given your partner a lap dance and Striptease?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
9- If you could have three wishes, what would they be? Why?
Do you watch it? What is your favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would you do it again, and would you rather 2 females or 2 males?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
15~ Have you ever been “in love”? Who? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
61~ How willing would you be to try new sexual positions?
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?
19- What’s your favorite fairytale? What’s your least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
52~ What are your hobbies?
76~ Have you had a threesome? Care to Share?
The Ice Breaker Questions
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
*** Questions about Relationships/Past ***
What have you learned about me that was new and/or surprising?
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,
Can you Deep Throat? Do you like the taste of yourself?
What is your view on sex? Meaning, When/Where/ How often/
If you say it, I will stop, and we can talk about it when you are ready.
48~ Do you have any siblings? Are you close to your family?
28- What are some things that people do that irritate you?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Would you allow me to clean every part of your body with my soapy hands and fingers?
If YES, was it with 2 men or 2 women? Did you enjoy it?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
45~ How do you feel about me blindfolding you? How about blindfolding me?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
33- If you could visit any time period, when would you pick? Please explain why?
60~ How important is oral sex? Do you like receiving? Do you like giving?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
20- What’s your favorite candy? What’s your least favorite?
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…
Master/Slave Boss/Maid
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Take the short quiz here @ Discover Your Love Language® - The 5 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?
82~ Do you have any fantasies involving Role-Playing?
Do you have a favorite? Is it ok if your partner does?
That one or two things that made you go hmmmm, OMG or wow!
What have you learned about yourself that you did not before this?
67~ Do you like it when your partner moans and/or is vocal during sex?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
15- What's your favorite saying? What word or phrase is your least favorite?
8- What are your thoughts on politics?
What was the longest? What was the shortest?
34- Ever been to a concert? What was your favorite? Who would you like to see?
26~ What side of the bed do you sleep on?
Would you ever want to be woken up with oral and/or intercourse?
(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- 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?
3- Should Pluto still be considered a planet? 4- How about smoking?
3- What’s your favorite smell? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Do you think this brought you closer together?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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…
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
23- What is your dream job? What was it as a child?
48~ Have you ever paid or been paid for sex?
32- What's your greatest talent? Can I see it right now?
5- Have you ever been hypnotized? Would you allow yourself to be?
36~ What is your favorite time of day to have sex/make love?
What is your favorite toy? Ever wanted to try a specific toy?
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.
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
92~ Have you ever had or have an STD? How many? What was it?
7-What do I do in bed that drives you wild? How about, what turns you off?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
47~ What would be your dream job and why?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
2- What’s your favorite color? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
15- What bad habit do you wish you could quit? Do you have any addictions?
13~ Is there a difference between, making love, having sex, and fucking?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Repairman/Lonely Wife Virgin/Experienced
51~ What tends to bring a smile to your face?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
22- What is your favorite childhood memory? What is your least favorite?
19~ Who/when was your first “heartbreak”?
5~ When you first started having sex, was it what you thought it would be?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
39~ What are your love languages?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
How old are you? Male or Female?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
How many times do you think you have “made love”?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
65~ Describe the best orgasm you’ve ever had? Care to share?
* Which of the following turns you on the most? Do you have any not on this list? 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?
10- List 5 of your top pet peeves.
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How many partners have you had oral sex with? Who? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
89~ Do you like taking showers together?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
9- What’s your favorite season and why? What’s your least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
84~ How do you feel about reading/listening to adult stories?
Do you like the “69” position? Do you prefer to be on top or bottom?
30~ What's something unexpected that turns you on?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
37- Do you like your name? If you could change it, what would you change it too?
Have you ever? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
3- What Superhero or Superpower would you want to be/have?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
27- What was/ is nickname? Does it have a meaning behind it?
Any that are a turn off?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
*** Questions About Me ***
If yes, what?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Do you like it when they show and tell you what they want?
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)
36- Do you play video games? What is your favorite? Do you a least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
What would you say to prove to yourself that it was really you?
12- What’s your favorite food? What’s your least favorite?
Does the thought excite you? Care to share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
13- What is the craziest/scariest thing you've ever done?
83~ How do you feel about Porn?
38~ Share your most embarrassing sexual memory?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
How well do you know me? And some of your thoughts about me
70~ Would/do you have/like anal sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
4- For a pet, Cat, dog or other?
42~ What’s your biggest regret in life?
1- What was your first impression of me? Has it changed?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
51~ Are you willing to play adult games with your partner?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
49~ How many times have you been married? Why did they end?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
13- How about having a certain hair cut/style?
*** What’s Your Favorite…? ***
64~ When was your very first orgasm? When was your first from having sex? Care to share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
18- How often do you drink alcohol? What is your favorite drink?
I would allow you to do it… What would you do to me?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
12- What is the weirdest thing you've ever eaten?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
How about if they talk dirty and/or call you names?
*** Deal Breaker Questions ***
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Please share Did you stop?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Would you mind if your partner watched it? How about together vs alone?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
53~ How much can you tell me about the one thing you are most passionate about?
*** Random Questions ***
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
52~ Are you willing to make “those types” of bets with your partner?
80~ Share your top three fantasies/desires. (Be detailed) 😊
9~ How many times over your lifetime do you think you have had sex so far?
11- How about if they like a certain sports team? 12-How about drinking too much?
If you win, what will you make them do?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
50~ How many children do you have? What are their ages?
34~ Do you like the lights on or off during sex?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Nurse/Patient Celebrity/Fan
1~ How old were you when you had your first kiss? Who? Care to Share?
Family Relation Age Play
62~ Have you used adult toys?
10~ How many dates are necessary before you to have sex with someone?
22- Do you have any birth marks? How about scars? Care to share how you got them?
11~ Have you ever been caught by your parents or children or others while having sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
6- Do you have dreams? Can you remember them? What do you usually dream about?