What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 04:59
17- Have you ever done drugs? Which ones? How often?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Doctor/Nurse Stripper/Client
19- Do/have you smoked? What do you prefer? How often?
11- List at least 5 things on your bucket list. Have you done any of them already?
33- If you could visit any time period, when would you pick? Please explain why?
What is one thing you've learned from life?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
11- What's your favorite restaurant? What’s your least favorite?
Model/Photographer Police/Criminal
What is the estimated number of people with an extra X chromosome?
3- What’s your favorite smell? Do you a least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
84~ How do you feel about reading/listening to adult stories?
What does it mean when you dream that your mother died?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
3- Should Pluto still be considered a planet? 4- How about smoking?
What was the longest? What was the shortest?
Can you write a poem or short story based on the first image that shows up on Pinterest?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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…
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Report: New Development in Trey Hendrickson Contract Situation - Sports Illustrated
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How about if they talk dirty and/or call you names?
What have you learned about yourself that you did not before this?
18- How often do you drink alcohol? What is your favorite drink?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
12- What is the weirdest thing you've ever eaten?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Do you think this brought you closer together?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
What misfortune led to an important discovery?
Does the thought excite you? Care to share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
70~ Would/do you have/like anal sex?
Trump Military Parade: Darcy cartoon - Cleveland.com
81~ Do you have any kinks and/or fetishes?
Escort/Client Job Applicant/Hiring Manager
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Has anyone ever had sex with their cousin? How did it start, and would you do it again?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Why is the world male-dominated?
92~ Everyone needs a “safe” word. What is yours?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
22- What is your favorite childhood memory? What is your least favorite?
47~ What would be your dream job and why?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
That one or two things that made you go hmmmm, OMG or wow!
Will you cheat again? How can, you be sure? Define what cheating is to you.
19~ Who/when was your first “heartbreak”?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
If NO, would you ever have one? Would it be with 2 men or 2 women?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
*** Deal Breaker Questions ***
12- What’s your favorite food? What’s your least favorite?
28- What are some things that people do that irritate you?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
What do you dislike about me? I asked you to be 100% honest.
Get this wrong and this could mean the end… :-) some funny, some not…
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?
Would you read them together?
Any that are a turn off?
Do you like the “69” position? Do you prefer to be on top or bottom?
65~ Describe the best orgasm you’ve ever had? Care to share?
83~ How do you feel about Porn?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
31- If given a chance to be immortal, would you take it? Why?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
61~ How willing would you be to try new sexual positions?
14- What is an embarrassing moment in your life? How about your most embarrassing?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
21~ What was the best date you ever went on? What has been the worst?
13- How about having a certain hair cut/style?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
If yes, what?
37- Do you like your name? If you could change it, what would you change it too?
Over time has your thoughts on sex changed?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
4- For a pet, Cat, dog or other?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How old are you? Male or Female?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
45~ How do you feel about me blindfolding you? How about blindfolding me?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
44~ Care to share something about yourself that no one else knows about you?
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- 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?
15- What's your favorite saying? What word or phrase is your 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)
Master/Slave Boss/Maid
51~ Are you willing to play adult games with your partner?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Would you ever want to be woken up with oral and/or intercourse?
92~ Have you ever had or have an STD? How many? What was it?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
*** Questions about Relationships/Past ***
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
76~ Have you had a threesome? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
48~ Have you ever paid or been paid for sex?
Nothing too Serious
32- What's your greatest talent? Can I see it right now?
17- What’s your favorite holiday? What’s your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
15- What bad habit do you wish you could quit? Do you have any addictions?
62~ Have you used adult toys?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Do you have a favorite? Is it ok if your partner does?
Can you Deep Throat? Do you like the taste of yourself?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
52~ Are you willing to make “those types” of bets with your partner?
10- List 5 of your top pet peeves.
82~ Do you have any fantasies involving Role-Playing?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
20- What’s your favorite candy? What’s your least favorite?
28~ What are some things that turn on? What is your biggest turn on?
2- What’s your favorite color? Do you a least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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?
Family Relation Age Play
13~ Is there a difference between, making love, having sex, and fucking?
1~ How old were you when you had your first kiss? Who? 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?
Would you do it again, and would you rather 2 females or 2 males?
You know that I will be 100% truthful, so ask.
22- Do you have any birth marks? How about scars? Care to share how you got them?
52~ What are your hobbies?
19- What’s your favorite fairytale? What’s your least favorite?
The Ice Breaker Questions
*** Questions About Me ***
What’s the longest time you gone without having sex, after, having it? How much time between the others?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
14- What's your favorite dessert? Do you a least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
67~ Do you like it when your partner moans and/or is vocal during sex?
21- What's your favorite way to spend a weekend or time off?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
48~ Do you have any siblings? Are you close to your family?
Would you mind if your partner watched it? How about together vs alone?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
7- What if a person smells a certain way? 8- How about smoking?
10- What is your favorite family tradition? What’s your least favorite?
Prisoner/Prison Guard Landlord/Tenant
36~ What is your favorite time of day to have sex/make love?
Please share Did you stop?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What is your favorite toy? Ever wanted to try a specific toy?
What is your view on sex? Meaning, When/Where/ How often/
If you say it, I will stop, and we can talk about it when you are ready.
*** What’s Your Favorite…? ***
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
42~ What’s your biggest regret in life?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Would /have you ever given your partner a lap dance and Striptease?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
26~ What side of the bed do you sleep on?
9- If you could have three wishes, what would they be? Why?
29- How superstitious are you?
How well do you know me? And some of your thoughts about me
34- Ever been to a concert? What was your favorite? Who would you like to see?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
What would you say to prove to yourself that it was really you?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
If YES, was it with 2 men or 2 women? Did you enjoy it?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
7- What are your thoughts on religion? Is there an afterlife?
80~ Share your top three fantasies/desires. (Be detailed) 😊
10~ How many dates are necessary before you to have sex with someone?
5~ When you first started having sex, was it what you thought it would be?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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- What Superhero or Superpower would you want to be/have?
25~ How do you feel about PDA? (Public Display of Affection)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Nurse/Patient Celebrity/Fan
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
How many times do you think you have “made love”?
Have you ever? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
11- How about if they like a certain sports team? 12-How about drinking too much?
30~ What's something unexpected that turns you on?
7-What do I do in bed that drives you wild? How about, what turns you off?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
71~ Would you give your partner a hand or foot job? Would you receive one?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
39~ What are your love languages?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
51~ What tends to bring a smile to your face?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Any that are a turn off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
49~ How many times have you been married? Why did they end?
Would you allow me to clean every part of your body with my soapy hands and fingers?
9~ How many times over your lifetime do you think you have had sex so far?
If you win, what will you make them do?
* Give a rating for each one (0-100)
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
53~ How much can you tell me about the one thing you are most passionate about?
13- What is the craziest/scariest thing you've ever done?
I would allow you to do it… What would you do to me?
33- Beach or Mountains? Or is there another place to like better?
Teacher/Student Stranger/One Night Stand
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,
18~ Who/when was your first “crush”?
8- What are your thoughts on politics?
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 have you learned about me that was new and/or surprising?
5- Have you ever been hypnotized? Would you allow yourself to be?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Repairman/Lonely Wife Virgin/Experienced
(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…)
89~ Do you like taking showers together?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What is your favorite position? Why?
9- What’s your favorite season and why? What’s your least favorite?
34~ Do you like the lights on or off during sex?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you watch it? What is your favorite?
29~ What are some things that turn you off? What is your biggest turn off?
50~ How many children do you have? What are their ages?
Do you like it when they show and tell you what they want?
How many partners have you had oral sex with? Who? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
1- What was your first impression of me? Has it changed?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
38~ Share your most embarrassing sexual memory?
1- What’s your favorite animal? Do you a least favorite?
*** Random Questions ***
40~ What’s the weirdest place you’ve ever had sex?
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?
11~ Have you ever been caught by your parents or children or others while having sex?
15~ Have you ever been “in love”? Who? Care to Share?