What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 07:20
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How many partners have you had oral sex with? Who? Care to Share?
Teacher/Student Stranger/One Night Stand
Person with measles visited Boston hotel, museum, airport, health officials warn - NBC Boston
Can you Deep Throat? Do you like the taste of yourself?
15- What's your favorite saying? What word or phrase is your least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Why do ugly men flirt with girls that are really hot?
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?
12- What’s your favorite food? What’s your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Why are there so many single moms in America?
Would you ever want to be woken up with oral and/or intercourse?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How was your JEE 2024 result like?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
33- Beach or Mountains? Or is there another place to like better?
47~ What would be your dream job and why?
In your humble opinion, why does the narcissist mistake kindness for weakness in some people?
21~ What was the best date you ever went on? What has been the worst?
52~ Are you willing to make “those types” of bets with your partner?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
6- Do you have dreams? Can you remember them? What do you usually dream about?
1- What was your first impression of me? Has it changed?
Family Relation Age Play
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 was your first cuckolding experience as a husband?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Do you think this brought you closer together?
Which is the most liked web series in India?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
How many times do you think you have “made love”?
How old are you? Male or Female?
What did your sister do to you that you can never forget?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
Why do so many autistic adults deal with self-hatred?
13- What is the craziest/scariest thing you've ever done?
*** Questions About Me ***
32- What's your greatest talent? Can I see it right now?
I dreamt my mother had died and I cried so much in my dream. What does it mean?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Can you share the entire summary of your spiritual life?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
53~ How much can you tell me about the one thing you are most passionate about?
Do you like it when they show and tell you what they want?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Do you watch it? What is your favorite?
If yes, what?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Would you mind if your partner watched it? How about together vs alone?
29- How superstitious are you?
*** Random Questions ***
29~ What are some things that turn you off? What is your biggest turn off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
14- What's your favorite dessert? Do you a least favorite?
Nurse/Patient Celebrity/Fan
Do you shave/trim your pubic hair? For you guys do you shave your balls?
11- What's your favorite restaurant? What’s your least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
If you win, what will you make them do?
18~ Who/when was your first “crush”?
What is your favorite toy? Ever wanted to try a specific toy?
76~ Have you had a threesome? Care to Share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
19- What’s your favorite fairytale? What’s your least favorite?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
19- Do/have you smoked? What do you prefer? How often?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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…
11~ Have you ever been caught by your parents or children or others while having sex?
28~ What are some things that turn on? What is your biggest turn on?
What do you dislike about me? I asked you to be 100% honest.
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- Should Pluto still be considered a planet? 4- How about smoking?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
18- How often do you drink alcohol? What is your favorite drink?
13- How about having a certain hair cut/style?
4- For a pet, Cat, dog or other?
61~ How willing would you be to try new sexual positions?
84~ How do you feel about reading/listening to adult stories?
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,
Over time has your thoughts on sex changed?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
80~ Share your top three fantasies/desires. (Be detailed) 😊
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
51~ Are you willing to play adult games with your partner?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
92~ Have you ever had or have an STD? How many? What was it?
17- What’s your favorite holiday? What’s your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you like the “69” position? Do you prefer to be on top or bottom?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
19~ Who/when was your first “heartbreak”?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
49~ How many times have you been married? Why did they end?
If NO, would you ever have one? Would it be with 2 men or 2 women?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
27- What was/ is nickname? Does it have a meaning behind it?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
51~ What tends to bring a smile to your face?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
40~ What’s the weirdest place you’ve ever had sex?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
3- What’s your favorite smell? Do you a least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
*** Deal Breaker Questions ***
Would /have you ever given your partner a lap dance and Striptease?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
7-What do I do in bed that drives you wild? How about, what turns you off?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
89~ Do you like taking showers together?
48~ Do you have any siblings? Are you close to your family?
15~ Have you ever been “in love”? Who? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
10~ How many dates are necessary before you to have sex with someone?
Get this wrong and this could mean the end… :-) some funny, some not…
The Ice Breaker Questions
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Does the thought excite you? Care to share?
What was the longest? What was the shortest?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
92~ Everyone needs a “safe” word. What is yours?
21- What's your favorite way to spend a weekend or time off?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
22- What is your favorite childhood memory? What is your least favorite?
Any that are a turn off?
What have you learned about me that was new and/or surprising?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
82~ Do you have any fantasies involving Role-Playing?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What have you learned about yourself that you did not before this?
38~ Share your most embarrassing sexual memory?
5~ When you first started having sex, was it what you thought it would be?
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?
Any that are a turn off?
13~ Is there a difference between, making love, having sex, and fucking?
If YES, was it with 2 men or 2 women? Did you enjoy it?
13- What’s your favorite drink? What’s your least favorite?
9- If you could have three wishes, what would they be? Why?
*** Questions about Relationships/Past ***
44~ Care to share something about yourself that no one else knows about you?
How well do you know me? And some of your thoughts about me
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Doctor/Nurse Stripper/Client
10- What is your favorite family tradition? What’s your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
33- If you could visit any time period, when would you pick? Please explain why?
Repairman/Lonely Wife Virgin/Experienced
8- What are your thoughts on politics?
10- List 5 of your top pet peeves.
How about if they talk dirty and/or call you names?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
81~ Do you have any kinks and/or fetishes?
Will you cheat again? How can, you be sure? Define what cheating is to you.
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
48~ Have you ever paid or been paid for sex?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
*** What’s Your Favorite…? ***
23- What is your dream job? What was it as a child?
Would you do it again, and would you rather 2 females or 2 males?
That one or two things that made you go hmmmm, OMG or wow!
26~ What side of the bed do you sleep on?
9~ How many times over your lifetime do you think you have had sex so far?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
I would allow you to do it… What would you do to me?
52~ What are your hobbies?
62~ Have you used adult toys?
17- Have you ever done drugs? Which ones? How often?
Do you have a favorite? Is it ok if your partner does?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
20- What’s your favorite candy? What’s your least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
30~ What's something unexpected that turns you on?
28- What are some things that people do that irritate you?
* Give a rating for each one (0-100)
(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…)
What is your view on sex? Meaning, When/Where/ How often/
Would you read them together?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
70~ Would/do you have/like anal sex?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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?
25~ How do you feel about PDA? (Public Display of Affection)
Have you ever? Care to Share?
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?
If you say it, I will stop, and we can talk about it when you are ready.
1~ How old were you when you had your first kiss? Who? 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?
8- What's your favorite flavor of ice cream? Do you a least favorite?
31- If given a chance to be immortal, would you take it? Why?
12- What is the weirdest thing you've ever eaten?
3- What Superhero or Superpower would you want to be/have?
11- List at least 5 things on your bucket list. Have you done any of them already?
5- Have you ever been hypnotized? Would you allow yourself to be?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
11- How about if they like a certain sports team? 12-How about drinking too much?
Nothing too Serious
67~ Do you like it when your partner moans and/or is vocal during sex?
7- What are your thoughts on religion? Is there an afterlife?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
34~ Do you like the lights on or off during sex?
39~ What are your love languages?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
2- What’s your favorite color? Do you a least favorite?
Please share Did you stop?
Prisoner/Prison Guard Landlord/Tenant
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
83~ How do you feel about Porn?
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?
7- What if a person smells a certain way? 8- How about smoking?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Escort/Client Job Applicant/Hiring Manager
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Master/Slave Boss/Maid
34- Ever been to a concert? What was your favorite? Who would you like to see?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
36~ What is your favorite time of day to have sex/make love?
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)
Model/Photographer Police/Criminal
You know that I will be 100% truthful, so ask.
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
42~ What’s your biggest regret in life?
50~ How many children do you have? What are their ages?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
9- Is there something you’ve always wanted to ask me but you’re afraid?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
What is your favorite position? Why?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What would you say to prove to yourself that it was really you?