What is the most interesting question you can ask to get to know someone?
08.06.2025 20:07
9~ How many times over your lifetime do you think you have had sex so far?
40~ What’s the weirdest place you’ve ever had sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Can you share some of your favorite jokes that are not well-known but always make people laugh?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Would you ever want to be woken up with oral and/or intercourse?
Will you cheat again? How can, you be sure? Define what cheating is to you.
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
84~ How do you feel about reading/listening to adult stories?
7- What if a person smells a certain way? 8- How about smoking?
What does it mean when you dream that your mother died?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
60~ How important is oral sex? Do you like receiving? Do you like giving?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What are mean nicknames to call my sister? She is always so mean to me.
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Why has my ex moved on so fast after years of being together with me?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
26~ What side of the bed do you sleep on?
42~ What’s your biggest regret in life?
In the TV show Supernatural, why is God portrayed as cruel?
32- What's your greatest talent? Can I see it right now?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Can you Deep Throat? Do you like the taste of yourself?
92~ Have you ever had or have an STD? How many? What was it?
You know that I will be 100% truthful, so ask.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
11- How about if they like a certain sports team? 12-How about drinking too much?
Measles vaccinations drop as CDC updates travel guidance - Yahoo
How old are you? Male or Female?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
9- What’s your favorite season and why? What’s your least favorite?
Menopause Drug Reduces Breast Cancer Growth In Clinical Trial - ScienceAlert
1- What was your first impression of me? Has it changed?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
(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…)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
18~ Who/when was your first “crush”?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
*** What’s Your Favorite…? ***
34~ Do you like the lights on or off during sex?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you like the “69” position? Do you prefer to be on top or bottom?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What have you learned about yourself that you did not before this?
Repairman/Lonely Wife Virgin/Experienced
What have you learned about me that was new and/or surprising?
Get this wrong and this could mean the end… :-) some funny, some not…
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
How well do you know me? And some of your thoughts about me
Does the thought excite you? Care to share?
15~ Have you ever been “in love”? Who? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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…
Please share Did you stop?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
50~ How many children do you have? What are their ages?
11~ Have you ever been caught by your parents or children or others while having sex?
Master/Slave Boss/Maid
I would allow you to do it… What would you do to me?
2- What’s your favorite color? Do you a least favorite?
What was the longest? What was the shortest?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
29~ What are some things that turn you off? What is your biggest turn off?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Would you read them together?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Do you like it when they show and tell you what they want?
Would you allow me to clean every part of your body with my soapy hands and fingers?
61~ How willing would you be to try new sexual positions?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Nothing too Serious
What is your view on sex? Meaning, When/Where/ How often/
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Teacher/Student Stranger/One Night Stand
25~ How do you feel about PDA? (Public Display of Affection)
The Ice Breaker Questions
48~ Have you ever paid or been paid for sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
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)
Have you ever? Care to Share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Would you mind if your partner watched it? How about together vs alone?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
How many times do you think you have “made love”?
76~ Have you had a threesome? Care to Share?
*** Deal Breaker Questions ***
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
70~ Would/do you have/like anal sex?
Escort/Client Job Applicant/Hiring Manager
28~ What are some things that turn on? What is your biggest turn on?
33- If you could visit any time period, when would you pick? Please explain why?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
8- What are your thoughts on politics?
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,
36~ What is your favorite time of day to have sex/make love?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
51~ Are you willing to play adult games with your partner?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you think this brought you closer together?
39~ What are your love languages?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
What would you say to prove to yourself that it was really you?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If YES, was it with 2 men or 2 women? Did you enjoy it?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
65~ Describe the best orgasm you’ve ever had? Care to share?
7-What do I do in bed that drives you wild? How about, what turns you off?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
38~ Share your most embarrassing sexual memory?
19~ Who/when was your first “heartbreak”?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
1- What’s your favorite animal? Do you a least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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?
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?
Model/Photographer Police/Criminal
52~ What are your hobbies?
20- What’s your favorite candy? What’s your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
17- What’s your favorite holiday? What’s your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Doctor/Nurse Stripper/Client
13- How about having a certain hair cut/style?
49~ How many times have you been married? Why did they end?
What do you dislike about me? I asked you to be 100% honest.
37- Do you like your name? If you could change it, what would you change it too?
31- If given a chance to be immortal, would you take it? Why?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
62~ Have you used adult toys?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
6- Do you have dreams? Can you remember them? What do you usually dream about?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
How many partners have you had oral sex with? Who? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
5~ When you first started having sex, was it what you thought it would be?
13- What’s your favorite drink? What’s your least favorite?
*** Questions About Me ***
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
13~ Is there a difference between, making love, having sex, and fucking?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
14- What's your favorite dessert? Do you a least favorite?
47~ What would be your dream job and why?
53~ How much can you tell me about the one thing you are most passionate about?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
33- Beach or Mountains? Or is there another place to like better?
81~ Do you have any kinks and/or fetishes?
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?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
If you win, what will you make them do?
10- List 5 of your top pet peeves.
30~ What's something unexpected that turns you on?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
3- Should Pluto still be considered a planet? 4- How about smoking?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
3- What Superhero or Superpower would you want to be/have?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
45~ How do you feel about me blindfolding you? How about blindfolding me?
36- Do you play video games? What is your favorite? Do you a least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
80~ Share your top three fantasies/desires. (Be detailed) 😊
11- List at least 5 things on your bucket list. Have you done any of them already?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
82~ Do you have any fantasies involving Role-Playing?
Prisoner/Prison Guard Landlord/Tenant
67~ Do you like it when your partner moans and/or is vocal during sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Nurse/Patient Celebrity/Fan
Over time has your thoughts on sex changed?
7~ How many times in one day have you had sex? Who/When/Where? 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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
21- What's your favorite way to spend a weekend or time off?
18- How often do you drink alcohol? What is your favorite drink?
Would you do it again, and would you rather 2 females or 2 males?
*** Random Questions ***
Any that are a turn off?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
21~ What was the best date you ever went on? What has been the worst?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
14- What is an embarrassing moment in your life? How about your most embarrassing?
22- What is your favorite childhood memory? What is your least favorite?
48~ Do you have any siblings? Are you close to your family?
13- What is the craziest/scariest thing you've ever done?
83~ How do you feel about Porn?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
89~ Do you like taking showers together?
9- If you could have three wishes, what would they be? Why?
52~ Are you willing to make “those types” of bets with your partner?
* Give a rating for each one (0-100)
If you say it, I will stop, and we can talk about it when you are ready.
12- What is the weirdest thing you've ever eaten?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
8- What's your favorite flavor of ice cream? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
1~ How old were you when you had your first kiss? Who? Care to Share?
23- What is your dream job? What was it as a child?
That one or two things that made you go hmmmm, OMG or wow!
12- What’s your favorite food? What’s your least favorite?
29- How superstitious are you?
*** Questions about Relationships/Past ***
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If yes, what?
15- What's your favorite saying? What word or phrase is your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
22- Do you have any birth marks? How about scars? Care to share how you got them?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Family Relation Age Play
28- What are some things that people do that irritate you?
15- What bad habit do you wish you could quit? Do you have any addictions?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Any that are a turn off?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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…
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Do you watch it? What is your favorite?
51~ What tends to bring a smile to your face?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
17- Have you ever done drugs? Which ones? How often?
44~ Care to share something about yourself that no one else knows about you?
10~ How many dates are necessary before you to have sex with someone?
Would /have you ever given your partner a lap dance and Striptease?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How about if they talk dirty and/or call you names?
10- What is your favorite family tradition? What’s your least favorite?
4- For a pet, Cat, dog or other?