What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 02:39
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Nurse/Patient Celebrity/Fan
Do you like the “69” position? Do you prefer to be on top or bottom?
Have you ever? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
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?
34~ Do you like the lights on or off during sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
1~ How old were you when you had your first kiss? Who? Care to Share?
Is the Chinese economy currently collapsing? If not, what could potentially cause it to collapse?
1- What was your first impression of me? Has it changed?
Do you like it when they show and tell you what they want?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
How would you feel if your girlfriend had dick pics on her phone?
How old are you? Male or Female?
84~ How do you feel about reading/listening to adult stories?
5~ When you first started having sex, was it what you thought it would be?
Why is Donald Trump criticized by so many people?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
61~ How willing would you be to try new sexual positions?
36- Do you play video games? What is your favorite? Do you a least favorite?
What are some things that normal people do that religious people call sins?
50~ How many children do you have? What are their ages?
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?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What is a common thought that keeps people up at night? Why do some people experience this?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Do you have a favorite? Is it ok if your partner does?
62~ Have you used adult toys?
What do you say after "Hi" when chatting?
Would you ever want to be woken up with oral and/or intercourse?
* Give a rating for each one (0-100)
13~ Is there a difference between, making love, having sex, and fucking?
Where and how did ballet originate?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What are my 10 favorite rock record album opening tracks?
45~ How do you feel about me blindfolding you? How about blindfolding me?
51~ Are you willing to play adult games with your partner?
29- How superstitious are you?
92~ Have you ever had or have an STD? How many? What was it?
How well do you know me? And some of your thoughts about me
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
67~ Do you like it when your partner moans and/or is vocal during sex?
Has anyone ever worn leather pants? Are they comfortable?
44~ Care to share something about yourself that no one else knows about you?
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…
14- What is an embarrassing moment in your life? How about your most embarrassing?
Is it true that most women like alpha males?
Nothing too Serious
Doctor/Nurse Stripper/Client
49~ If you could, would you want to be the opposite sex for a day, week, or year?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
13- How about having a certain hair cut/style?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
1- What’s your favorite animal? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
Master/Slave Boss/Maid
*** Questions About Me ***
19~ Who/when was your first “heartbreak”?
If yes, what?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
42~ What’s your biggest regret in life?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
*** What’s Your Favorite…? ***
12- What’s your favorite food? What’s your least favorite?
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?
89~ Do you like taking showers together?
16~ Do you believe in “soulmates”? Have you found yours? Who? 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?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? 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…)
81~ Do you have any kinks and/or fetishes?
83~ How do you feel about Porn?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
47~ What would be your dream job and why?
That one or two things that made you go hmmmm, OMG or wow!
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Over time has your thoughts on sex changed?
29~ What are some things that turn you off? What is your biggest turn off?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
49~ How many times have you been married? Why did they end?
11- What's your favorite restaurant? What’s your least favorite?
You know that I will be 100% truthful, so ask.
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
27- What was/ is nickname? Does it have a meaning behind it?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
15- What bad habit do you wish you could quit? Do you have any addictions?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Teacher/Student Stranger/One Night Stand
13- What is the craziest/scariest thing you've ever done?
If you say it, I will stop, and we can talk about it when you are ready.
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
6- What’s your favorite TV series? Do you have a favorite genre? 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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
15- What's your favorite saying? What word or phrase is your least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
32- What's your greatest talent? Can I see it right now?
9- If you could have three wishes, what would they be? Why?
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?
10- List 5 of your top pet peeves.
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
23- What is your dream job? What was it as a child?
36~ What is your favorite time of day to have sex/make love?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
18~ Who/when was your first “crush”?
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,
19- Do/have you smoked? What do you prefer? How often?
Repairman/Lonely Wife Virgin/Experienced
7- What if a person smells a certain way? 8- How about smoking?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
56~ Would you ever go to a strip club with your partner? Have you ever been? 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?
14- What's your favorite dessert? 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?
48~ Have you ever paid or been paid for sex?
15~ Have you ever been “in love”? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
76~ Have you had a threesome? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Model/Photographer Police/Criminal
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Family Relation Age Play
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
7- What are your thoughts on religion? Is there an afterlife?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
92~ Everyone needs a “safe” word. What is yours?
Do you watch it? What is your favorite?
*** Questions about Relationships/Past ***
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
13- What’s your favorite drink? What’s your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3- What Superhero or Superpower would you want to be/have?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Would you allow me to clean every part of your body with my soapy hands and fingers?
70~ Would/do you have/like anal sex?
2- What’s your favorite color? Do you a least favorite?
What was the longest? What was the shortest?
7-What do I do in bed that drives you wild? How about, what turns you off?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
22- Do you have any birth marks? How about scars? Care to share how you got them?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Would you do it again, and would you rather 2 females or 2 males?
28~ What are some things that turn on? What is your biggest turn on?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Please share Did you stop?
How many partners have you had oral sex with? Who? Care to Share?
38~ Share your most embarrassing sexual memory?
20- What’s your favorite candy? What’s your least favorite?
Would you mind if your partner watched it? How about together vs alone?
What have you learned about yourself that you did not before this?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
25~ How do you feel about PDA? (Public Display of Affection)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
11- How about if they like a certain sports team? 12-How about drinking too much?
12- What is the weirdest thing you've ever eaten?
33- Beach or Mountains? Or is there another place to like better?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
21- What's your favorite way to spend a weekend or time off?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
19- What’s your favorite fairytale? What’s your least favorite?
10- What is your favorite family tradition? What’s your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
8- What's your favorite flavor of ice cream? Do you a least favorite?
*** Random Questions ***
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
11- List at least 5 things on your bucket list. Have you done any of them already?
Would you read them together?
37- Do you like your name? If you could change it, what would you change it too?
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?
What is your favorite position? Why?
How about if they talk dirty and/or call you names?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
3- Should Pluto still be considered a planet? 4- How about smoking?
39~ What are your love languages?
17- What’s your favorite holiday? What’s your least favorite?
*** Deal Breaker Questions ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
If you win, what will you make them do?
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?
52~ Are you willing to make “those types” of bets with your partner?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
I would allow you to do it… What would you do to me?
3- What’s your favorite smell? Do you a least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
9~ How many times over your lifetime do you think you have had sex so far?
Does the thought excite you? Care to share?
What would you say to prove to yourself that it was really you?
21~ What was the best date you ever went on? What has been the worst?
Can you Deep Throat? Do you like the taste of yourself?
52~ What are your hobbies?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
31- If given a chance to be immortal, would you take it? Why?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
8- What are your thoughts on politics?
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)
82~ Do you have any fantasies involving Role-Playing?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
17- Have you ever done drugs? Which ones? How often?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Would /have you ever given your partner a lap dance and Striptease?
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…
What is your favorite toy? Ever wanted to try a specific toy?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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 many times do you think you have “made love”?
5- Have you ever been hypnotized? Would you allow yourself to be?
10~ How many dates are necessary before you to have sex with someone?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
The Ice Breaker Questions
51~ What tends to bring a smile to your face?
26~ What side of the bed do you sleep on?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What have you learned about me that was new and/or surprising?
If NO, would you ever have one? Would it be with 2 men or 2 women?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What is your view on sex? Meaning, When/Where/ How often/
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Prisoner/Prison Guard Landlord/Tenant
Escort/Client Job Applicant/Hiring Manager
30~ What's something unexpected that turns you on?
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Get this wrong and this could mean the end… :-) some funny, some not…
9- Is there something you’ve always wanted to ask me but you’re afraid?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
9- What’s your favorite season and why? What’s your least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
11~ Have you ever been caught by your parents or children or others while having sex?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
65~ Describe the best orgasm you’ve ever had? Care to share?
4- For a pet, Cat, dog or other?
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?
33- If you could visit any time period, when would you pick? Please explain why?
48~ Do you have any siblings? Are you close to your family?
Do you think this brought you closer together?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
60~ How important is oral sex? Do you like receiving? Do you like giving?
What do you dislike about me? I asked you to be 100% honest.
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
28- What are some things that people do that irritate you?
Any that are a turn off?