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