What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 03:25
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
(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…)
22- Do you have any birth marks? How about scars? Care to share how you got them?
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?
What does it mean when we dream about demons, ghosts, monsters, etc.?
Nothing too Serious
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
How can you know if they are your twin flame and not limerence or obsession?
*** What’s Your Favorite…? ***
Get this wrong and this could mean the end… :-) some funny, some not…
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
What do you remember that 95% of us have forgotten?
If you win, what will you make them do?
17- Have you ever done drugs? Which ones? How often?
26~ What side of the bed do you sleep on?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Any that are a turn off?
Does the thought excite you? Care to share?
Nurse/Patient Celebrity/Fan
How about if they talk dirty and/or call you names?
22- What is your favorite childhood memory? What is your least favorite?
13- What’s your favorite drink? What’s your least favorite?
21~ What was the best date you ever went on? What has been the worst?
11- List at least 5 things on your bucket list. Have you done any of them already?
5 foods to add to your diet to prevent magnesium deficiency - Times of India
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
17- What’s your favorite holiday? What’s your least favorite?
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?
What Happens to Your Body When You Eat Watermelon Regularly - Verywell Health
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,
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
AMD Stock Soars as Piper Sandler Raises Price Target After 'Advancing AI' Event - Investopedia
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Is it true that Jehovah's witnesses once thought the world would end in 1975?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
11~ Have you ever been caught by your parents or children or others while having sex?
Model/Photographer Police/Criminal
71~ Would you give your partner a hand or foot job? Would you receive one?
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)
52~ What are your hobbies?
Skin Aging Reduced by Molecules from Bacteria in the Blood - Neuroscience News
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Prisoner/Prison Guard Landlord/Tenant
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
All four iPhone 17 models just tipped for ‘metalens’ upgrade - Tom's Guide
9- If you could have three wishes, what would they be? Why?
Would /have you ever given your partner a lap dance and Striptease?
33- Beach or Mountains? Or is there another place to like better?
2- What’s your favorite color? Do you a least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
44~ Care to share something about yourself that no one else knows about you?
39~ What are your love languages?
If you say it, I will stop, and we can talk about it when you are ready.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Do you think this brought you closer together?
10- What is your favorite family tradition? What’s your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
18~ Who/when was your first “crush”?
19~ Who/when was your first “heartbreak”?
67~ Do you like it when your partner moans and/or is vocal during sex?
25~ How do you feel about PDA? (Public Display of Affection)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
How well do you know me? And some of your thoughts about me
5- Have you ever been hypnotized? Would you allow yourself to be?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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…
8- What are your thoughts on politics?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
29~ What are some things that turn you off? What is your biggest turn off?
1- What’s your favorite animal? Do you a least favorite?
*** Questions About Me ***
Over time has your thoughts on sex changed?
Can you Deep Throat? Do you like the taste of yourself?
10~ How many dates are necessary before you to have sex with someone?
How many times do you think you have “made love”?
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?
31- If given a chance to be immortal, would you take it? Why?
36~ What is your favorite time of day to have sex/make love?
37- Do you like your name? If you could change it, what would you change it too?
Do you like it when they show and tell you what they want?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Do you like the “69” position? Do you prefer to be on top or bottom?
What is your view on sex? Meaning, When/Where/ How often/
9~ How many times over your lifetime do you think you have had sex so far?
81~ Do you have any kinks and/or fetishes?
9- Is there something you’ve always wanted to ask me but you’re afraid?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
42~ What’s your biggest regret in life?
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?
11- How about if they like a certain sports team? 12-How about drinking too much?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
18- How often do you drink alcohol? What is your favorite drink?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
1- What was your first impression of me? Has it changed?
13- How about having a certain hair cut/style?
51~ Are you willing to play adult games with your partner?
Would you read them together?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Master/Slave Boss/Maid
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?
* Give a rating for each one (0-100)
34~ Do you like the lights on or off during sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Please share Did you stop?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
7- What if a person smells a certain way? 8- How about smoking?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
*** Deal Breaker Questions ***
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
52~ Are you willing to make “those types” of bets with your partner?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
I would allow you to do it… What would you do to me?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
3- Should Pluto still be considered a planet? 4- How about smoking?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What was the longest? What was the shortest?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you watch it? What is your favorite?
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…
15- What bad habit do you wish you could quit? Do you have any addictions?
11- What's your favorite restaurant? What’s your least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
Would you do it again, and would you rather 2 females or 2 males?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
7-What do I do in bed that drives you wild? How about, what turns you off?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
62~ Have you used adult toys?
48~ Have you ever paid or been paid for sex?
What would you say to prove to yourself that it was really you?
Have you ever? Care to Share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
20- What’s your favorite candy? What’s your least favorite?
32- What's your greatest talent? Can I see it right now?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
92~ Everyone needs a “safe” word. What is yours?
40~ What’s the weirdest place you’ve ever had sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
That one or two things that made you go hmmmm, OMG or wow!
How old are you? Male or Female?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
If yes, what?
12- What’s your favorite food? What’s your least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Repairman/Lonely Wife Virgin/Experienced
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
45~ How do you feel about me blindfolding you? How about blindfolding me?
4- For a pet, Cat, dog or other?
38~ Share your most embarrassing sexual memory?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
29- How superstitious are you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
The Ice Breaker Questions
Escort/Client Job Applicant/Hiring Manager
Would you mind if your partner watched it? How about together vs alone?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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?
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?
89~ Do you like taking showers together?
60~ How important is oral sex? Do you like receiving? Do you like giving?
What do you dislike about me? I asked you to be 100% honest.
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
21- What's your favorite way to spend a weekend or time off?
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?
Family Relation Age Play
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
What have you learned about me that was new and/or surprising?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Teacher/Student Stranger/One Night Stand
14- What's your favorite dessert? Do you a least favorite?
48~ Do you have any siblings? Are you close to your family?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
49~ How many times have you been married? Why did they end?
23- What is your dream job? What was it as a child?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
What have you learned about yourself that you did not before this?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What is your favorite position? Why?
19- Do/have you smoked? What do you prefer? How often?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
82~ Do you have any fantasies involving Role-Playing?
19- What’s your favorite fairytale? What’s your least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
15- What's your favorite saying? What word or phrase is your least favorite?
3- What Superhero or Superpower would you want to be/have?
70~ Would/do you have/like anal sex?
Doctor/Nurse Stripper/Client
*** Questions about Relationships/Past ***
76~ Have you had a threesome? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
*** Random Questions ***
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
51~ What tends to bring a smile to your face?
How many partners have you had oral sex with? Who? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
33- If you could visit any time period, when would you pick? Please explain why?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
80~ Share your top three fantasies/desires. (Be detailed) 😊
10- List 5 of your top pet peeves.
28~ What are some things that turn on? What is your biggest turn on?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
27- What was/ is nickname? Does it have a meaning behind it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
3- What’s your favorite smell? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
50~ How many children do you have? What are their ages?
Will you cheat again? How can, you be sure? Define what cheating is to you.
You know that I will be 100% truthful, so ask.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
61~ How willing would you be to try new sexual positions?
Any that are a turn off?
12- What is the weirdest thing you've ever eaten?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
1~ How old were you when you had your first kiss? Who? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
28- What are some things that people do that irritate you?
Would you ever want to be woken up with oral and/or intercourse?
47~ What would be your dream job and why?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
8- What's your favorite flavor of ice cream? Do you a least favorite?
30~ What's something unexpected that turns you on?
6- Do you have dreams? Can you remember them? What do you usually dream about?
84~ How do you feel about reading/listening to adult stories?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
83~ How do you feel about Porn?
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?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?