What is the most interesting question you can ask to get to know someone?
11.06.2025 04:49
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Do you think this brought you closer together?
Nurse/Patient Celebrity/Fan
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
*** Questions About Me ***
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
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?
How does Arab culture and values differ from western culture and values?
How many partners have you had oral sex with? Who? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
1- What’s your favorite animal? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
7- What are your thoughts on religion? Is there an afterlife?
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10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
3- What’s your favorite smell? Do you a least favorite?
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Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
*** Random Questions ***
Do you as a gay male enjoy the feeling of getting a penis in your anus?
19~ Who/when was your first “heartbreak”?
49~ How many times have you been married? Why did they end?
4- For a pet, Cat, dog or other?
What are some reasons why men may not want to date a woman who can pay her own bills?
33- If you could visit any time period, when would you pick? Please explain why?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
18- How often do you drink alcohol? What is your favorite drink?
47~ What would be your dream job and why?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
* Give a rating for each one (0-100)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Will you cheat again? How can, you be sure? Define what cheating is to you.
83~ How do you feel about Porn?
What are some common examples of condescending behavior?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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)
48~ Have you ever paid or been paid for sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
How many times do you think you have “made love”?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
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…
36- Do you play video games? What is your favorite? Do you a 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…
Would you ever want to be woken up with oral and/or intercourse?
25~ How do you feel about PDA? (Public Display of Affection)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Does the thought excite you? Care to share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
If you win, what will you make them do?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
38~ Share your most embarrassing sexual memory?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
Get this wrong and this could mean the end… :-) some funny, some not…
11- List at least 5 things on your bucket list. Have you done any of them already?
22- What is your favorite childhood memory? What is your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
9- What’s your favorite season and why? What’s your least favorite?
51~ What tends to bring a smile to your face?
How about if they talk dirty and/or call you names?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What was the longest? What was the shortest?
65~ Describe the best orgasm you’ve ever had? Care to share?
Family Relation Age Play
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
53~ How much can you tell me about the one thing you are most passionate about?
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?
Teacher/Student Stranger/One Night Stand
82~ Do you have any fantasies involving Role-Playing?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Escort/Client Job Applicant/Hiring Manager
80~ Share your top three fantasies/desires. (Be detailed) 😊
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
21~ What was the best date you ever went on? What has been the worst?
Would you mind if your partner watched it? How about together vs alone?
2- What’s your favorite color? Do you a least favorite?
If yes, what?
What have you learned about yourself that you did not before this?
44~ Care to share something about yourself that no one else knows about you?
Nothing too Serious
84~ How do you feel about reading/listening to adult stories?
30~ What's something unexpected that turns you on?
92~ Everyone needs a “safe” word. What is yours?
I would allow you to do it… What would you do to me?
60~ How important is oral sex? Do you like receiving? Do you like giving?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
29- How superstitious are you?
61~ How willing would you be to try new sexual positions?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Model/Photographer Police/Criminal
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
27- What was/ is nickname? Does it have a meaning behind it?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
33- Beach or Mountains? Or is there another place to like better?
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?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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?
Repairman/Lonely Wife Virgin/Experienced
70~ Would/do you have/like anal sex?
Over time has your thoughts on sex changed?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Have you ever? 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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
11- What's your favorite restaurant? What’s your least favorite?
10~ How many dates are necessary before you to have sex with someone?
9- If you could have three wishes, what would they be? Why?
19- What’s your favorite fairytale? What’s your least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
10- List 5 of your top pet peeves.
13- What is the craziest/scariest thing you've ever done?
11~ Have you ever been caught by your parents or children or others while having sex?
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”?
50~ How many children do you have? What are their ages?
What is your favorite position? Why?
1~ How old were you when you had your first kiss? Who? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
36~ What is your favorite time of day to have sex/make love?
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?
76~ Have you had a threesome? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
How well do you know me? And some of your thoughts about me
7-What do I do in bed that drives you wild? How about, what turns you off?
92~ Have you ever had or have an STD? How many? What was it?
32- What's your greatest talent? Can I see it right now?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
*** Deal Breaker Questions ***
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
1- What was your first impression of me? Has it changed?
14- What's your favorite dessert? Do you a least favorite?
42~ What’s your biggest regret in life?
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?
5~ When you first started having sex, was it what you thought it would be?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
13- What’s your favorite drink? What’s your least favorite?
Any that are a turn off?
*** Questions about Relationships/Past ***
14- What is an embarrassing moment in your life? How about your most embarrassing?
If YES, was it with 2 men or 2 women? Did you enjoy it?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
52~ What are your hobbies?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What is your favorite toy? Ever wanted to try a specific toy?
Master/Slave Boss/Maid
7- What if a person smells a certain way? 8- How about smoking?
62~ Have you used adult toys?
Any that are a turn off?
17- What’s your favorite holiday? What’s your least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
9~ How many times over your lifetime do you think you have had sex so far?
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
40~ What’s the weirdest place you’ve ever had sex?
13- How about having a certain hair cut/style?
71~ Would you give your partner a hand or foot job? Would you receive one?
23- What is your dream job? What was it as a child?
Would you read them together?
31- If given a chance to be immortal, would you take it? Why?
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
12- What’s your favorite food? What’s your least favorite?
How old are you? Male or Female?
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?
Would /have you ever given your partner a lap dance and Striptease?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
15- What's your favorite saying? What word or phrase is your least favorite?
(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…)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
That one or two things that made you go hmmmm, OMG or wow!
17- Have you ever done drugs? Which ones? How often?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
15~ Have you ever been “in love”? Who? Care to Share?
39~ What are your love languages?
28- What are some things that people do that irritate you?
Do you like it when they show and tell you what they want?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
21- What's your favorite way to spend a weekend or time off?
15- What bad habit do you wish you could quit? Do you have any addictions?
*** What’s Your Favorite…? ***
Can you Deep Throat? Do you like the taste of yourself?
What do you dislike about me? I asked you to be 100% honest.
Do you have a favorite? Is it ok if your partner does?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What is your view on sex? Meaning, When/Where/ How often/
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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,
81~ Do you have any kinks and/or fetishes?
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?
8- What are your thoughts on politics?
Would you allow me to clean every part of your body with my soapy hands and fingers?
28~ What are some things that turn on? What is your biggest turn on?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
3- Should Pluto still be considered a planet? 4- How about smoking?
You know that I will be 100% truthful, so ask.
12- What is the weirdest thing you've ever eaten?
Doctor/Nurse Stripper/Client
What have you learned about me that was new and/or surprising?
67~ Do you like it when your partner moans and/or is vocal during sex?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
5- Have you ever been hypnotized? Would you allow yourself to be?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you watch it? What is your favorite?
89~ Do you like taking showers together?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Please share Did you stop?
What would you say to prove to yourself that it was really you?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
51~ Are you willing to play adult games with your partner?
11- How about if they like a certain sports team? 12-How about drinking too much?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
48~ Do you have any siblings? Are you close to your family?
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
The Ice Breaker Questions
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
34~ Do you like the lights on or off during sex?