What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 06:56
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
3- What’s your favorite smell? Do you a least favorite?
Is there a correlation between being a medium and mental health?
Family Relation Age Play
49~ How many times have you been married? Why did they end?
What is your view on sex? Meaning, When/Where/ How often/
10- What is your favorite family tradition? What’s your least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
33- Beach or Mountains? Or is there another place to like better?
What are women's true thoughts and feelings on bestiality?
13- What’s your favorite drink? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Repairman/Lonely Wife Virgin/Experienced
Why do flat-Earthers think the Earth is flat?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
If you say it, I will stop, and we can talk about it when you are ready.
44~ Care to share something about yourself that no one else knows about you?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Would /have you ever given your partner a lap dance and Striptease?
A Fifth Force of Nature May Have Been Discovered Inside Atoms - ScienceAlert
89~ Do you like taking showers together?
92~ Everyone needs a “safe” word. What is yours?
*** Questions About Me ***
What is an easy way to get your driver's license?
What is your favorite position? Why?
80~ Share your top three fantasies/desires. (Be detailed) 😊
How many partners have you had oral sex with? Who? Care to Share?
What was your most memorable experience catching a fraudulent car seller?
*** Questions about Relationships/Past ***
21- What's your favorite way to spend a weekend or time off?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What is the difference between heaven and heavens?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
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....)
Why are Trump's and Khan's experiences with authorities in the US and Pakistan similar?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
51~ Are you willing to play adult games with your partner?
Which city should one visit between Nice and Cannes? Why?
52~ Are you willing to make “those types” of bets with your partner?
14- What's your favorite dessert? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Thanks to FIFA, Atlanta’s first-ever Club World Cup game was underwhelming - AJC.com
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
33- If you could visit any time period, when would you pick? Please explain why?
14- What is an embarrassing moment in your life? How about your most embarrassing?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
Over time has your thoughts on sex changed?
Will you cheat again? How can, you be sure? Define what cheating is to you.
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What have you learned about yourself that you did not before this?
51~ What tends to bring a smile to your face?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Would you do it again, and would you rather 2 females or 2 males?
*** Random Questions ***
Any that are a turn off?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Would you allow me to clean every part of your body with my soapy hands and fingers?
You know that I will be 100% truthful, so ask.
20- What’s your favorite candy? What’s your least favorite?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
18- How often do you drink alcohol? What is your favorite drink?
11- What's your favorite restaurant? What’s your least favorite?
Do you have a favorite? Is it ok if your partner does?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
9- If you could have three wishes, what would they be? Why?
What is your favorite toy? Ever wanted to try a specific toy?
*** What’s Your Favorite…? ***
Please share Did you stop?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
15- What's your favorite saying? What word or phrase is your least favorite?
62~ Have you used adult toys?
1- What was your first impression of me? Has it changed?
Would you read them together?
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?
How well do you know me? And some of your thoughts about me
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
52~ What are your hobbies?
Do you like it when they show and tell you what they want?
65~ Describe the best orgasm you’ve ever had? Care to share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
17- What’s your favorite holiday? What’s your least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Have you ever? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
5~ When you first started having sex, was it what you thought it would be?
Nurse/Patient Celebrity/Fan
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
40~ What’s the weirdest place you’ve ever had sex?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
10~ How many dates are necessary before you to have sex with someone?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
19- Do/have you smoked? What do you prefer? How often?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
28~ What are some things that turn on? What is your biggest turn on?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
10- List 5 of your top pet peeves.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
What was the longest? What was the shortest?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
15~ Have you ever been “in love”? Who? Care to Share?
83~ How do you feel about Porn?
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?
37- Do you like your name? If you could change it, what would you change it too?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
13~ Is there a difference between, making love, having sex, and fucking?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
38~ Share your most embarrassing sexual memory?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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?
92~ Have you ever had or have an STD? How many? What was it?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
34- Ever been to a concert? What was your favorite? Who would you like to see?
3- Should Pluto still be considered a planet? 4- How about smoking?
28- What are some things that people do that irritate you?
53~ How much can you tell me about the one thing you are most passionate about?
If YES, was it with 2 men or 2 women? Did you enjoy it?
70~ Would/do you have/like anal sex?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Do you think this brought you closer together?
12- What is the weirdest thing you've ever eaten?
82~ Do you have any fantasies involving Role-Playing?
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…
11~ Have you ever been caught by your parents or children or others while having sex?
*** Deal Breaker Questions ***
9~ How many times over your lifetime do you think you have had sex so far?
29- How superstitious are you?
If you win, what will you make them do?
(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…)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
How about if they talk dirty and/or call you names?
Prisoner/Prison Guard Landlord/Tenant
Do you like the “69” position? Do you prefer to be on top or bottom?
4- For a pet, Cat, dog or other?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Doctor/Nurse Stripper/Client
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
The Ice Breaker Questions
11- List at least 5 things on your bucket list. Have you done any of them already?
34~ Do you like the lights on or off during sex?
22- Do you have any birth marks? How about scars? Care to share how you got them?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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)
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?
23- What is your dream job? What was it as a child?
How many times do you think you have “made love”?
Model/Photographer Police/Criminal
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Does the thought excite you? Care to share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
7-What do I do in bed that drives you wild? How about, what turns you off?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
18~ Who/when was your first “crush”?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Would you ever want to be woken up with oral and/or intercourse?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
17- Have you ever done drugs? Which ones? How often?
81~ Do you have any kinks and/or fetishes?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
27- What was/ is nickname? Does it have a meaning behind it?
48~ Do you have any siblings? Are you close to your family?
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?
47~ What would be your dream job and why?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Teacher/Student Stranger/One Night Stand
Would you allow me to shave your legs? How about your pubic hair? How about shower 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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
* Give a rating for each one (0-100)
26~ What side of the bed do you sleep on?
I would allow you to do it… What would you do to me?
If yes, what?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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,
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
Nothing too Serious
Do you watch it? What is your favorite?
29~ What are some things that turn you off? What is your biggest turn off?
1~ How old were you when you had your first kiss? Who? Care to Share?
3- What Superhero or Superpower would you want to be/have?
15- What bad habit do you wish you could quit? Do you have any addictions?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What would you say to prove to yourself that it was really you?
12- What’s your favorite food? What’s your least favorite?
13- What is the craziest/scariest thing you've ever done?
19~ Who/when was your first “heartbreak”?
That one or two things that made you go hmmmm, OMG or wow!
36~ What is your favorite time of day to have sex/make love?
71~ Would you give your partner a hand or foot job? Would you receive one?
Get this wrong and this could mean the end… :-) some funny, some not…
6- Do you have dreams? Can you remember them? What do you usually dream about?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
11- How about if they like a certain sports team? 12-How about drinking too much?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
9- What’s your favorite season and why? What’s your least favorite?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
19- What’s your favorite fairytale? What’s your least favorite?
Master/Slave Boss/Maid
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?
21~ What was the best date you ever went on? What has been the worst?
32- What's your greatest talent? Can I see it right now?
What do you dislike about me? I asked you to be 100% honest.
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…
7- What are your thoughts on religion? Is there an afterlife?
84~ How do you feel about reading/listening to adult stories?
How old are you? Male or Female?
13- How about having a certain hair cut/style?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Escort/Client Job Applicant/Hiring Manager
25~ How do you feel about PDA? (Public Display of Affection)
39~ What are your love languages?
What have you learned about me that was new and/or surprising?
Any that are a turn off?
Can you Deep Throat? Do you like the taste of yourself?
50~ How many children do you have? What are their ages?
1- What’s your favorite animal? 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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
22- What is your favorite childhood memory? What is your least favorite?
76~ Have you had a threesome? Care to Share?
42~ What’s your biggest regret in life?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
2- What’s your favorite color? Do you a least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
8- What are your thoughts on politics?
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?
61~ How willing would you be to try new sexual positions?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?