What is the most interesting question you can ask to get to know someone?
Last Updated: 29.06.2025 14:41
7- What if a person smells a certain way? 8- How about smoking?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Want to lower your cholesterol? Try a daily cup of this common bean - The Independent
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Master/Slave Boss/Maid
48~ Have you ever paid or been paid for sex?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Samsung Galaxy S26 Ultra to continue trend of disappointing batteries - PhoneArena
34~ Do you like the lights on or off during sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
If you say it, I will stop, and we can talk about it when you are ready.
The Upsetting Truth About What Wildfire Smoke Does to Your Body - Gizmodo
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
9- If you could have three wishes, what would they be? Why?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Mario Kart World dev comments on why non-Mario characters aren’t included - Nintendo Everything
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
28- What are some things that people do that irritate you?
6- Do you have dreams? Can you remember them? What do you usually dream about?
There Is A Very Particular Reason Why Baboons Travel In Straight Lines - IFLScience
10~ How many dates are necessary before you to have sex with someone?
I would allow you to do it… What would you do to me?
Teacher/Student Stranger/One Night Stand
What do flat Earthers think causes the "magical downward force"?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
23- What is your dream job? What was it as a child?
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)
42~ What’s your biggest regret in life?
21~ What was the best date you ever went on? What has been the worst?
65~ Describe the best orgasm you’ve ever had? Care to share?
All New GTA Online Vehicles In Money Fronts Update And Prices Revealed - RockstarINTEL
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
11- How about if they like a certain sports team? 12-How about drinking too much?
Please share Did you stop?
Why is Canada letting too many Indians in Canada?
What is your view on sex? Meaning, When/Where/ How often/
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
27- What was/ is nickname? Does it have a meaning behind it?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
How well do you know me? And some of your thoughts about me
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?
Why should you never do drugs? Will this story absolutely shock you?
47~ What would be your dream job and why?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
26~ What side of the bed do you sleep on?
21- What's your favorite way to spend a weekend or time off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
71~ Would you give your partner a hand or foot job? Would you receive one?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What is your favorite position? Why?
Any that are a turn off?
52~ What are your hobbies?
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
36- Do you play video games? What is your favorite? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
33- If you could visit any time period, when would you pick? Please explain why?
50~ How many children do you have? What are their ages?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
12- What’s your favorite food? What’s your least favorite?
3- What Superhero or Superpower would you want to be/have?
60~ How important is oral sex? Do you like receiving? Do you like giving?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
*** Random Questions ***
13- How about having a certain hair cut/style?
Can you Deep Throat? Do you like the taste of yourself?
70~ Would/do you have/like anal sex?
*** Questions About Me ***
34- Ever been to a concert? What was your favorite? Who would you like to see?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
4- For a pet, Cat, dog or other?
Get this wrong and this could mean the end… :-) some funny, some not…
89~ Do you like taking showers together?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Would you do it again, and would you rather 2 females or 2 males?
18~ Who/when was your first “crush”?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
52~ Are you willing to make “those types” of bets with your partner?
11- What's your favorite restaurant? What’s your least favorite?
19- What’s your favorite fairytale? 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?
That one or two things that made you go hmmmm, OMG or wow!
10- List 5 of your top pet peeves.
19~ Who/when was your first “heartbreak”?
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?
19- Do/have you smoked? What do you prefer? How often?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Would you ever want to be woken up with oral and/or intercourse?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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,
If NO, would you ever have one? Would it be with 2 men or 2 women?
Would /have you ever given your partner a lap dance and Striptease?
Repairman/Lonely Wife Virgin/Experienced
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
13- What is the craziest/scariest thing you've ever done?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
22- Do you have any birth marks? How about scars? Care to share how you got them?
20- What’s your favorite candy? What’s your least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
53~ How much can you tell me about the one thing you are most passionate about?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
What have you learned about yourself that you did not before this?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Over time has your thoughts on sex changed?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Does the thought excite you? Care to share?
62~ Have you used adult toys?
How many times do you think you have “made love”?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
11~ Have you ever been caught by your parents or children or others while having sex?
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?
38~ Share your most embarrassing sexual memory?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
36~ What is your favorite time of day to have sex/make love?
You know that I will be 100% truthful, so ask.
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
8- What are your thoughts on politics?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
28~ What are some things that turn on? What is your biggest turn on?
29~ What are some things that turn you off? What is your biggest turn off?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
37- Do you like your name? If you could change it, what would you change it too?
45~ How do you feel about me blindfolding you? How about blindfolding me?
17- Have you ever done drugs? Which ones? How often?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
1~ How old were you when you had your first kiss? Who? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
2- What’s your favorite color? Do you a least favorite?
3- What’s your favorite smell? Do you a least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Escort/Client Job Applicant/Hiring Manager
29- How superstitious are you?
17- What’s your favorite holiday? 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~ If you could, would you want to be the opposite sex for a day, week, or year?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
9- Is there something you’ve always wanted to ask me but you’re afraid?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
(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…)
Do you think this brought you closer together?
51~ What tends to bring a smile to your face?
7-What do I do in bed that drives you wild? How about, what turns you off?
* Give a rating for each one (0-100)
Do you like the “69” position? Do you prefer to be on top or bottom?
9- What’s your favorite season and why? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
5- Have you ever been hypnotized? Would you allow yourself to be?
22- What is your favorite childhood memory? What is your least favorite?
Family Relation Age Play
11- List at least 5 things on your bucket list. Have you done any of them already?
25~ How do you feel about PDA? (Public Display of Affection)
33- Beach or Mountains? Or is there another place to like better?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
*** Questions about Relationships/Past ***
Would you mind if your partner watched it? How about together vs alone?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
76~ Have you had a threesome? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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?
If you win, what will you make them do?
9~ How many times over your lifetime do you think you have had sex so far?
Do you watch it? What is your favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
How about if they talk dirty and/or call you names?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Doctor/Nurse Stripper/Client
44~ Care to share something about yourself that no one else knows about you?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Prisoner/Prison Guard Landlord/Tenant
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Nothing too Serious
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
14- What's your favorite dessert? Do you a least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
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?
81~ Do you have any kinks and/or fetishes?
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?
7- What’s your favorite book? Do you have a favorite genre? 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?
39~ What are your love languages?
13~ Is there a difference between, making love, having sex, and fucking?
Model/Photographer Police/Criminal
15- What bad habit do you wish you could quit? Do you have any addictions?
30~ What's something unexpected that turns you on?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Would you read them together?
Nurse/Patient Celebrity/Fan
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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…
Will you cheat again? How can, you be sure? Define what cheating is to you.
3- Should Pluto still be considered a planet? 4- How about smoking?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
83~ How do you feel about Porn?
The Ice Breaker Questions
31- If given a chance to be immortal, would you take it? Why?
If yes, what?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
12- What is the weirdest thing you've ever eaten?
48~ Do you have any siblings? Are you close to your family?
32- What's your greatest talent? Can I see it right now?
51~ Are you willing to play adult games with your partner?
How many partners have you had oral sex with? Who? Care to Share?
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…
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
8- What's your favorite flavor of ice cream? Do you a least favorite?
What was the longest? What was the shortest?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
13- What’s your favorite drink? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If YES, was it with 2 men or 2 women? Did you enjoy it?
67~ Do you like it when your partner moans and/or is vocal during sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
*** What’s Your Favorite…? ***
Have you ever? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
84~ How do you feel about reading/listening to adult stories?
What is your favorite toy? Ever wanted to try a specific toy?
5~ When you first started having sex, was it what you thought it would be?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What have you learned about me that was new and/or surprising?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
61~ How willing would you be to try new sexual positions?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
49~ How many times have you been married? Why did they end?
92~ Have you ever had or have an STD? How many? What was it?
1- What’s your favorite animal? Do you a least favorite?
*** Deal Breaker Questions ***
7- What are your thoughts on religion? Is there an afterlife?
15~ Have you ever been “in love”? Who? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
1- What was your first impression of me? Has it changed?
Any that are a turn off?
How old are you? Male or Female?
Do you like it when they show and tell you what they want?
What do you dislike about me? I asked you to be 100% honest.
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
What would you say to prove to yourself that it was really you?
80~ Share your top three fantasies/desires. (Be detailed) 😊