What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 08:27
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Please share Did you stop?
Billie Eilish Kisses Nat Wolff in Italy amid Romance Rumors - AOL.com
11~ Have you ever been caught by your parents or children or others while having sex?
19- What’s your favorite fairytale? What’s your least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
32- What's your greatest talent? Can I see it right now?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
17- What’s your favorite holiday? What’s your least favorite?
How many partners have you had oral sex with? Who? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
21- What's your favorite way to spend a weekend or time off?
23- What is your dream job? What was it as a child?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Does the thought excite you? Care to share?
Would you ever want to be woken up with oral and/or intercourse?
Infrared contact lens enables humans to see in dark - DW
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Is it ok for someone to crossdress in public?
* Give a rating for each one (0-100)
25~ How do you feel about PDA? (Public Display of Affection)
18~ Who/when was your first “crush”?
8- What are your thoughts on politics?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Hinge CEO Justin McLeod says dating AI chatbots is ‘playing with fire’ - The Verge
Have you ever? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
28~ What are some things that turn on? What is your biggest turn on?
Why does my vagina always itch so badly after my periods?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
What is your favorite toy? Ever wanted to try a specific toy?
3- Should Pluto still be considered a planet? 4- How about smoking?
Why do some people have loving parents and some do not?
10- What is your favorite family tradition? What’s your least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
1- What was your first impression of me? Has it changed?
How many times do you think you have “made love”?
7- What if a person smells a certain way? 8- How about smoking?
9- Is there something you’ve always wanted to ask me but you’re afraid?
How can you tell if someone is cunning?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Would /have you ever given your partner a lap dance and Striptease?
Can people who have never met you tell if you are a covert narcissist?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
13- How about having a certain hair cut/style?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you allow me to clean every part of your body with my soapy hands and fingers?
36~ What is your favorite time of day to have sex/make love?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Nurse/Patient Celebrity/Fan
49~ How many times have you been married? Why did they end?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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?
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?
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…
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Any that are a turn 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)
22- What is your favorite childhood memory? What is your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
*** Random Questions ***
52~ What are your hobbies?
10- List 5 of your top pet peeves.
33- If you could visit any time period, when would you pick? Please explain why?
12- What’s your favorite food? What’s your least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
7-What do I do in bed that drives you wild? How about, what turns you off?
38~ Share your most embarrassing sexual memory?
If NO, would you ever have one? Would it be with 2 men or 2 women?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
15- What bad habit do you wish you could quit? Do you have any addictions?
You know that I will be 100% truthful, so ask.
If yes, what?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
13- What is the craziest/scariest thing you've ever done?
83~ How do you feel about Porn?
34~ Do you like the lights on or off during sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
1- What’s your favorite animal? Do you a least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
15- What's your favorite saying? What word or phrase is your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
51~ What tends to bring a smile to your face?
If you say it, I will stop, and we can talk about it when you are ready.
62~ Have you used adult toys?
19~ Who/when was your first “heartbreak”?
10~ How many dates are necessary before you to have sex with someone?
Would you read them together?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
44~ Care to share something about yourself that no one else knows about you?
5~ When you first started having sex, was it what you thought it would be?
51~ Are you willing to play adult games with your partner?
4- For a pet, Cat, dog or other?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Do you think this brought you closer together?
Nothing too Serious
71~ Would you give your partner a hand or foot job? Would you receive one?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
9- If you could have three wishes, what would they be? Why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
*** What’s Your Favorite…? ***
1~ How old were you when you had your first kiss? Who? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
7- What are your thoughts on religion? Is there an afterlife?
If you win, what will you make them do?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
39~ What are your love languages?
Will you cheat again? How can, you be sure? Define what cheating is to you.
What have you learned about me that was new and/or surprising?
3- What Superhero or Superpower would you want to be/have?
How well do you know me? And some of your thoughts about me
I would allow you to do it… What would you do to me?
40~ What’s the weirdest place you’ve ever had sex?
48~ Have you ever paid or been paid for sex?
How about if they talk dirty and/or call you names?
52~ Are you willing to make “those types” of bets with your partner?
What is your view on sex? Meaning, When/Where/ How often/
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
70~ Would/do you have/like anal sex?
92~ Have you ever had or have an STD? How many? What was it?
92~ Everyone needs a “safe” word. What is yours?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
47~ What would be your dream job and why?
18- How often do you drink alcohol? What is your favorite drink?
Do you like the “69” position? Do you prefer to be on top or bottom?
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…
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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
13- What’s your favorite drink? 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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Repairman/Lonely Wife Virgin/Experienced
48~ Do you have any siblings? Are you close to your family?
14- What's your favorite dessert? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
50~ How many children do you have? What are their ages?
2- What’s your favorite color? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
12- What is the weirdest thing you've ever eaten?
33- Beach or Mountains? Or is there another place to like better?
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?
Can you Deep Throat? Do you like the taste of yourself?
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,
76~ Have you had a threesome? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Get this wrong and this could mean the end… :-) some funny, some not…
9~ How many times over your lifetime do you think you have had sex so far?
Model/Photographer Police/Criminal
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Do you watch it? What is your favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
*** Questions about Relationships/Past ***
What do you dislike about me? I asked you to be 100% honest.
61~ How willing would you be to try new sexual positions?
22- Do you have any birth marks? How about scars? Care to share how you got them?
5- Have you ever been hypnotized? Would you allow yourself to be?
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?
Over time has your thoughts on sex changed?
*** Deal Breaker Questions ***
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
11- How about if they like a certain sports team? 12-How about drinking too much?
That one or two things that made you go hmmmm, OMG or wow!
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
26~ What side of the bed do you sleep on?
Any that are a turn off?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
28- What are some things that people do that irritate you?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
67~ Do you like it when your partner moans and/or is vocal during sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
84~ How do you feel about reading/listening to adult stories?
What have you learned about yourself that you did not before this?
89~ Do you like taking showers together?
What was the longest? What was the shortest?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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?
How old are you? Male or Female?
Would you mind if your partner watched it? How about together vs alone?
11- What's your favorite restaurant? What’s your least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
The Ice Breaker Questions
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
20- What’s your favorite candy? What’s your least favorite?
What would you say to prove to yourself that it was really you?
Teacher/Student Stranger/One Night Stand
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Family Relation Age Play
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Would you do it again, and would you rather 2 females or 2 males?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Escort/Client Job Applicant/Hiring Manager
11- List at least 5 things on your bucket list. Have you done any of them already?
31- If given a chance to be immortal, would you take it? Why?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Doctor/Nurse Stripper/Client
21~ What was the best date you ever went on? What has been the worst?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
If YES, was it with 2 men or 2 women? Did you enjoy it?
Master/Slave Boss/Maid
65~ Describe the best orgasm you’ve ever had? Care to share?
42~ What’s your biggest regret in life?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
81~ Do you have any kinks and/or fetishes?
*** Questions About Me ***
9- What’s your favorite season and why? What’s your least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
53~ How much can you tell me about the one thing you are most passionate about?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
29- How superstitious are you?
(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…)
Prisoner/Prison Guard Landlord/Tenant
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?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
36- Do you play video games? What is your favorite? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
82~ Do you have any fantasies involving Role-Playing?
30~ What's something unexpected that turns you on?
37- Do you like your name? If you could change it, what would you change it too?
13~ Is there a difference between, making love, having sex, and fucking?
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?
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 is your favorite position? Why?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
29~ What are some things that turn you off? What is your biggest turn off?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
17- Have you ever done drugs? Which ones? How often?
Do you like it when they show and tell you what they want?
19- Do/have you smoked? What do you prefer? How often?
80~ Share your top three fantasies/desires. (Be detailed) 😊