What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 01:45
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Do you think this brought you closer together?
76~ Have you had a threesome? Care to Share?
Can you name a female actress who has had bad timing or luck in her film career?
10- What is your favorite family tradition? What’s your least favorite?
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?
*** What’s Your Favorite…? ***
What’s the saddest thing you’ve seen at your job?
65~ Describe the best orgasm you’ve ever had? Care to share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
42~ What’s your biggest regret in life?
Was Michael Jackson really an innocent person?
28~ What are some things that turn on? What is your biggest turn on?
17- Have you ever done drugs? Which ones? How often?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Why do some men like anal 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?
What have you learned about yourself that you did not before this?
Would /have you ever given your partner a lap dance and Striptease?
Is visiting holy shrines (dargahs) or graves haraam in Islam?
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…
*** Questions about Relationships/Past ***
What is your favorite toy? Ever wanted to try a specific toy?
How did it feel to take your first gay BBC?
5~ When you first started having sex, was it what you thought it would be?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What is the reason behind some people wearing trunks instead of speedos when swimming in pools?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
11- List at least 5 things on your bucket list. Have you done any of them already?
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?
What is your view on sex? Meaning, When/Where/ How often/
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Do you like the “69” position? Do you prefer to be on top or bottom?
Can you write a letter to your first love without mentioning his/her name?
How many partners have you had oral sex with? Who? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
9- If you could have three wishes, what would they be? Why?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
How old are you? Male or Female?
49~ How many times have you been married? Why did they end?
Would you read them together?
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?
7- What are your thoughts on religion? Is there an afterlife?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
31- If given a chance to be immortal, would you take it? Why?
92~ Everyone needs a “safe” word. What is yours?
*** Deal Breaker Questions ***
Do you have a favorite? Is it ok if your partner does?
You know that I will be 100% truthful, so ask.
15- What's your favorite saying? What word or phrase is your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
Model/Photographer Police/Criminal
That one or two things that made you go hmmmm, OMG or wow!
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Repairman/Lonely Wife Virgin/Experienced
51~ What tends to bring a smile to your face?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
34- Ever been to a concert? What was your favorite? Who would you like to see?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
3- What Superhero or Superpower would you want to be/have?
4- For a pet, Cat, dog or other?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
53~ How much can you tell me about the one thing you are most passionate about?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
9- Is there something you’ve always wanted to ask me but you’re afraid?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
48~ Do you have any siblings? Are you close to your family?
(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…)
12- What’s your favorite food? What’s your least favorite?
Please share Did you stop?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Do you watch it? What is your favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
18- How often do you drink alcohol? What is your favorite drink?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
3- What’s your favorite smell? Do you a least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
If you say it, I will stop, and we can talk about it when you are ready.
Escort/Client Job Applicant/Hiring Manager
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Would you do it again, and would you rather 2 females or 2 males?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
Get this wrong and this could mean the end… :-) some funny, some not…
The Ice Breaker Questions
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
19- Do/have you smoked? What do you prefer? How often?
67~ Do you like it when your partner moans and/or is vocal during sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
37- Do you like your name? If you could change it, what would you change it too?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
9~ How many times over your lifetime do you think you have had sex so far?
84~ How do you feel about reading/listening to adult stories?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
7-What do I do in bed that drives you wild? How about, what turns you off?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
19~ Who/when was your first “heartbreak”?
81~ Do you have any kinks and/or fetishes?
45~ How do you feel about me blindfolding you? How about blindfolding me?
62~ Have you used adult toys?
14- What is an embarrassing moment in your life? How about your most embarrassing?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
47~ What would be your dream job and why?
How well do you know me? And some of your thoughts about me
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Family Relation Age Play
1~ How old were you when you had your first kiss? Who? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
52~ Are you willing to make “those types” of bets with your partner?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
89~ Do you like taking showers together?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
83~ How do you feel about Porn?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
10~ How many dates are necessary before you to have sex with someone?
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)
Prisoner/Prison Guard Landlord/Tenant
If yes, what?
10- List 5 of your top pet peeves.
11- What's your favorite restaurant? What’s your least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
11~ Have you ever been caught by your parents or children or others while having sex?
50~ How many children do you have? What are their ages?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Master/Slave Boss/Maid
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
71~ Would you give your partner a hand or foot job? Would you receive one?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
1- What’s your favorite animal? Do you a least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
29- How superstitious are you?
29~ What are some things that turn you off? What is your biggest turn off?
*** Questions About Me ***
Would you mind if your partner watched it? How about together vs alone?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
If you win, what will you make them do?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
30~ What's something unexpected that turns you on?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Nurse/Patient Celebrity/Fan
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…
3- Should Pluto still be considered a planet? 4- How about smoking?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
39~ What are your love languages?
2- What’s your favorite color? Do you a least favorite?
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,
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
If NO, would you ever have one? Would it be with 2 men or 2 women?
What was the longest? What was the shortest?
26~ What side of the bed do you sleep on?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Any that are a turn off?
44~ Care to share something about yourself that no one else knows about you?
12- What is the weirdest thing you've ever eaten?
38~ Share your most embarrassing sexual memory?
70~ Would/do you have/like anal sex?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
17- What’s your favorite holiday? What’s your least favorite?
23- What is your dream job? What was it as a child?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
80~ Share your top three fantasies/desires. (Be detailed) 😊
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What have you learned about me that was new and/or surprising?
20- What’s your favorite candy? 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?
Can you Deep Throat? Do you like the taste of yourself?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
1- What was your first impression of me? Has it changed?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Nothing too Serious
82~ Do you have any fantasies involving Role-Playing?
15- What bad habit do you wish you could quit? Do you have any addictions?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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)
33- If you could visit any time period, when would you pick? Please explain why?
13- How about having a certain hair cut/style?
* Give a rating for each one (0-100)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Does the thought excite you? Care to share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What is your favorite position? Why?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Teacher/Student Stranger/One Night Stand
If YES, was it with 2 men or 2 women? Did you enjoy it?
27- What was/ is nickname? Does it have a meaning behind it?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Will you cheat again? How can, you be sure? Define what cheating is to you.
9- What’s your favorite season and why? What’s your least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
I would allow you to do it… What would you do to me?
What do you dislike about me? I asked you to be 100% honest.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
36- Do you play video games? What is your favorite? Do you a least favorite?
What would you say to prove to yourself that it was really you?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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?
25~ How do you feel about PDA? (Public Display of Affection)
18~ Who/when was your first “crush”?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
7- What if a person smells a certain way? 8- How about smoking?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
51~ Are you willing to play adult games with your partner?
21- What's your favorite way to spend a weekend or time off?
Do you like it when they show and tell you what they want?
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?
*** Random Questions ***
Doctor/Nurse Stripper/Client
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?
42~ Ever been spanked 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?
13~ Is there a difference between, making love, having sex, and fucking?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
15~ Have you ever been “in love”? Who? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
How many times do you think you have “made love”?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you ever want to be woken up with oral and/or intercourse?
61~ How willing would you be to try new sexual positions?
How about if they talk dirty and/or call you names?
14- What's your favorite dessert? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
5- Have you ever been hypnotized? Would you allow yourself to be?
8- What are your thoughts on politics?
36~ What is your favorite time of day to have sex/make love?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Over time has your thoughts on sex changed?
52~ What are your hobbies?
33- Beach or Mountains? Or is there another place to like better?
22- Do you have any birth marks? How about scars? Care to share how you got them?
48~ Have you ever paid or been paid for sex?
Have you ever? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
19- What’s your favorite fairytale? What’s your least favorite?
28- What are some things that people do that irritate you?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
34~ Do you like the lights on or off during sex?
13- What is the craziest/scariest thing you've ever done?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?