What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 00:13
Will you cheat again? How can, you be sure? Define what cheating is to you.
48~ Do you have any siblings? Are you close to your family?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Would you read them together?
52~ Are you willing to make “those types” of bets with your partner?
65~ Describe the best orgasm you’ve ever had? Care to share?
What does the Bible say about the Antichrist? How will we know when he arrives on the scene?
If you win, what will you make them do?
That one or two things that made you go hmmmm, OMG or wow!
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What is the best reply if your boyfriend asks you,"why do you love me?"
You know that I will be 100% truthful, so ask.
What is your favorite position? Why?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
What are some prime examples of gibberish from the bible?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
1~ How old were you when you had your first kiss? Who? Care to Share?
13- How about having a certain hair cut/style?
Have you ever been humiliated in front of a group of girls and enjoyed it?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you like it when they show and tell you what they want?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Why do people who were very kind and loving once become cold-hearted?
8- What are your thoughts on politics?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
31- If given a chance to be immortal, would you take it? Why?
What discoveries in AI research have changed our understanding of intelligence evolution?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
What is the scariest thing that ever happened in your life?
20- What’s your favorite candy? What’s your least favorite?
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?
Do you have a favorite? Is it ok if your partner does?
I would allow you to do it… What would you do to me?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What's the most sordid activity you've ever seen or heard about at a bachelorette party?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
50~ How many children do you have? What are their ages?
47~ What would be your dream job and why?
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?
Do handsome guys intimidate women or people in general?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
13~ Is there a difference between, making love, having sex, and fucking?
Have you ever? Care to Share?
What makes someone feel "rich enough" in different societies?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
29~ What are some things that turn you off? What is your biggest turn off?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
3- What’s your favorite smell? Do you a least favorite?
How about if they talk dirty and/or call you names?
Would you do it again, and would you rather 2 females or 2 males?
13- What’s your favorite drink? What’s your least favorite?
4- For a pet, Cat, dog or other?
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
The Ice Breaker Questions
Will you kiss after your partner has gone down on you? Swallow or spit semen?
1- What was your first impression of me? Has it changed?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
11~ Have you ever been caught by your parents or children or others while having sex?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
11- How about if they like a certain sports team? 12-How about drinking too much?
83~ How do you feel about Porn?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?
33- Beach or Mountains? Or is there another place to like better?
If you say it, I will stop, and we can talk about it when you are ready.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
15- What bad habit do you wish you could quit? Do you have any addictions?
6- Do you have dreams? Can you remember them? What do you usually dream about?
70~ Would/do you have/like anal sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
29- How superstitious are you?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
49~ How many times have you been married? Why did they end?
*** Questions About Me ***
44~ Care to share something about yourself that no one else knows about you?
What would you say to prove to yourself that it was really you?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
76~ Have you had a threesome? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
How old are you? Male or Female?
53~ How much can you tell me about the one thing you are most passionate about?
18~ Who/when was your first “crush”?
Please share Did you stop?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
12- What’s your favorite food? What’s your least favorite?
How many times do you think you have “made love”?
What do you dislike about me? I asked you to be 100% honest.
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Nurse/Patient Celebrity/Fan
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
84~ How do you feel about reading/listening to adult stories?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
42~ What’s your biggest regret in life?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
30~ What's something unexpected that turns you on?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
61~ How willing would you be to try new sexual positions?
14- What's your favorite dessert? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
23- What is your dream job? What was it as a child?
What have you learned about yourself that you did not before this?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
62~ Have you used adult toys?
(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…)
45~ How do you feel about me blindfolding you? How about blindfolding me?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Over time has your thoughts on sex changed?
40~ What’s the weirdest place you’ve ever had sex?
80~ Share your top three fantasies/desires. (Be detailed) 😊
92~ Have you ever had or have an STD? How many? What was it?
12- What is the weirdest thing you've ever eaten?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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 you mind if your partner watched it? How about together vs alone?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Get this wrong and this could mean the end… :-) some funny, some not…
Would you allow me to clean every part of your body with my soapy hands and fingers?
8- What's your favorite flavor of ice cream? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
5~ When you first started having sex, was it what you thought it would be?
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?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Nothing too Serious
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?
92~ Everyone needs a “safe” word. What is yours?
*** Deal Breaker Questions ***
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Would /have you ever given your partner a lap dance and Striptease?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
11- List at least 5 things on your bucket list. Have you done any of them already?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Doctor/Nurse Stripper/Client
Does the thought excite you? Care to share?
* Give a rating for each one (0-100)
19- What’s your favorite fairytale? What’s your least favorite?
19- Do/have you smoked? What do you prefer? How often?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
21- What's your favorite way to spend a weekend or time off?
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)
17- Have you ever done drugs? Which ones? How often?
Do you think this brought you closer together?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
7-What do I do in bed that drives you wild? How about, what turns you off?
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,
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…
10- List 5 of your top pet peeves.
34~ Do you like the lights on or off during sex?
39~ What are your love languages?
Can you Deep Throat? Do you like the taste of yourself?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Model/Photographer Police/Criminal
*** Random Questions ***
Any that are a turn off?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Any that are a turn off?
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
19~ Who/when was your first “heartbreak”?
How well do you know me? And some of your thoughts about me
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
28~ What are some things that turn on? What is your biggest turn on?
36~ What is your favorite time of day to have sex/make love?
7- What if a person smells a certain way? 8- How about smoking?
67~ Do you like it when your partner moans and/or is vocal during sex?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
11- What's your favorite restaurant? What’s your least favorite?
What was the longest? What was the shortest?
5- Have you ever been hypnotized? Would you allow yourself to be?
21~ What was the best date you ever went on? What has been the worst?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Teacher/Student Stranger/One Night Stand
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
If NO, would you ever have one? Would it be with 2 men or 2 women?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
22- What is your favorite childhood memory? What is your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
34- Ever been to a concert? What was your favorite? Who would you like to see?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
What is your view on sex? Meaning, When/Where/ How often/
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- What is the craziest/scariest thing you've ever done?
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?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Escort/Client Job Applicant/Hiring Manager
28- What are some things that people do that irritate you?
What is your favorite toy? Ever wanted to try a specific toy?
*** Questions about Relationships/Past ***
9- If you could have three wishes, what would they be? Why?
Do you watch it? What is your favorite?
81~ Do you have any kinks and/or fetishes?
7- What are your thoughts on religion? Is there an afterlife?
10- What is your favorite family tradition? What’s your least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
Prisoner/Prison Guard Landlord/Tenant
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How many partners have you had oral sex with? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
71~ Would you give your partner a hand or foot job? Would you receive one?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
14- What is an embarrassing moment in your life? How about your most embarrassing?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Family Relation Age Play
33- If you could visit any time period, when would you pick? Please explain why?
89~ Do you like taking showers together?
51~ Are you willing to play adult games with your partner?
2- What’s your favorite color? Do you a least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
26~ What side of the bed do you sleep on?
27- What was/ is nickname? Does it have a meaning behind it?
3- What Superhero or Superpower would you want to be/have?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
18- How often do you drink alcohol? What is your favorite drink?
17- What’s your favorite holiday? What’s your least favorite?
10~ How many dates are necessary before you to have sex with someone?
Master/Slave Boss/Maid
If YES, was it with 2 men or 2 women? Did you enjoy it?
If yes, what?
Do you like the “69” position? Do you prefer to be on top or bottom?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
48~ Have you ever paid or been paid for sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
*** What’s Your Favorite…? ***
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
9~ How many times over your lifetime do you think you have had sex so far?
52~ What are your hobbies?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
22- Do you have any birth marks? How about scars? Care to share how you got them?
51~ What tends to bring a smile to your face?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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…
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
9- What’s your favorite season and why? What’s your least favorite?
32- What's your greatest talent? Can I see it right now?
25~ How do you feel about PDA? (Public Display of Affection)
What have you learned about me that was new and/or surprising?
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?
Repairman/Lonely Wife Virgin/Experienced