What is the most interesting question you can ask to get to know someone?
08.06.2025 02:06
19- What’s your favorite fairytale? What’s your least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Trump, DOJ threaten Calif. with legal action, fines after trans athlete’s win - The Washington Post
11- List at least 5 things on your bucket list. Have you done any of them already?
82~ Do you have any fantasies involving Role-Playing?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Is it possible to achieve spiritual enlightenment while being in a romantic relationship?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Over time has your thoughts on sex changed?
33- If you could visit any time period, when would you pick? Please explain why?
What is the happy reality of our generation?
Any that are a turn off?
8- What are your thoughts on politics?
37- Do you like your name? If you could change it, what would you change it too?
Was Jimmy Carter a good President of the United States?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
10- List 5 of your top pet peeves.
60~ How important is oral sex? Do you like receiving? Do you like giving?
45~ How do you feel about me blindfolding you? How about blindfolding me?
34- Ever been to a concert? What was your favorite? Who would you like to see?
62~ Have you used adult toys?
How can I fall asleep fast at night?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
What was your best sex experience that still makes you horny?
Get this wrong and this could mean the end… :-) some funny, some not…
*** Random Questions ***
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Walking This Many Steps Per Day Can Cut Your Risk Of Early Death - HuffPost
Please share Did you stop?
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?
How well do you know me? And some of your thoughts about me
What is one thing which you cannot stop however hard you try?
Family Relation Age Play
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
What are some reasons why people may fear strong men?
If yes, what?
What is your view on sex? Meaning, When/Where/ How often/
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Who is the most trusted person in your life, and do they have the same trust on you?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
36~ What is your favorite time of day to have sex/make love?
29~ What are some things that turn you off? What is your biggest turn off?
☆ what's the thing that made u fell in love with your bias?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Have you ever? Care to Share?
Why did my ex-narcissist move so fast with his new supply marriage engagement moving in, etc.?
26~ What side of the bed do you sleep on?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
22- What is your favorite childhood memory? What is your least favorite?
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,
Would you read them together?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Would you allow me to clean every part of your body with my soapy hands and fingers?
29- How superstitious are you?
19~ Who/when was your first “heartbreak”?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
*** Questions About Me ***
* 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…)
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Do you have a favorite? Is it ok if your partner does?
If you win, what will you make them do?
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)
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
*** Deal Breaker Questions ***
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
15~ Have you ever been “in love”? Who? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
13- How about having a certain hair cut/style?
49~ How many times have you been married? Why did they end?
42~ What’s your biggest regret in life?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What have you learned about yourself that you did not before this?
52~ Are you willing to make “those types” of bets with your partner?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
14- What's your favorite dessert? Do you a least favorite?
12- What’s your favorite food? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Model/Photographer Police/Criminal
41~ Are there moments in your past that you would want to change? Please share 3 of them.
40~ What’s the weirdest place you’ve ever had sex?
81~ Do you have any kinks and/or fetishes?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
47~ What would be your dream job and why?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
17- What’s your favorite holiday? What’s your least favorite?
50~ How many children do you have? What are their ages?
I would allow you to do it… What would you do to me?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Do you watch it? What is your favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
53~ How much can you tell me about the one thing you are most passionate about?
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…
You know that I will be 100% truthful, so ask.
34~ Do you like the lights on or off during sex?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Nurse/Patient Celebrity/Fan
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
31- If given a chance to be immortal, would you take it? Why?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
21- What's your favorite way to spend a weekend or time off?
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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
52~ What are your hobbies?
10~ How many dates are necessary before you to have sex with someone?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
20- What’s your favorite candy? What’s your least favorite?
38~ Share your most embarrassing sexual memory?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
1~ How old were you when you had your first kiss? Who? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
28- What are some things that people do that irritate you?
What is your favorite toy? Ever wanted to try a specific toy?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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…
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!
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Prisoner/Prison Guard Landlord/Tenant
76~ Have you had a threesome? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
Does the thought excite you? 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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
11- How about if they like a certain sports team? 12-How about drinking too much?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
12- What is the weirdest thing you've ever eaten?
Master/Slave Boss/Maid
61~ How willing would you be to try new sexual positions?
Would you do it again, and would you rather 2 females or 2 males?
Doctor/Nurse Stripper/Client
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
How old are you? Male or Female?
*** Questions about Relationships/Past ***
71~ Would you give your partner a hand or foot job? Would you receive one?
9- Is there something you’ve always wanted to ask me but you’re afraid?
48~ Do you have any siblings? Are you close to your family?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
What have you learned about me that was new and/or surprising?
7- What if a person smells a certain way? 8- How about smoking?
19- Do/have you smoked? What do you prefer? How often?
Nothing too Serious
If NO, would you ever have one? Would it be with 2 men or 2 women?
25~ How do you feel about PDA? (Public Display of Affection)
48~ Have you ever paid or been paid for sex?
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?
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?
What is your favorite position? Why?
17- Have you ever done drugs? Which ones? How often?
7- What are your thoughts on religion? Is there an afterlife?
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?
3- What’s your favorite smell? Do you a least favorite?
70~ Would/do you have/like anal sex?
18- How often do you drink alcohol? What is your favorite drink?
2- What’s your favorite color? Do you a least favorite?
28~ What are some things that turn on? What is your biggest turn on?
18~ Who/when was your first “crush”?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
13- What’s your favorite drink? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
32- What's your greatest talent? Can I see it right now?
22- Do you have any birth marks? How about scars? Care to share how you got them?
80~ Share your top three fantasies/desires. (Be detailed) 😊
27- What was/ is nickname? Does it have a meaning behind it?
How many partners have you had oral sex with? Who? Care to Share?
Would you mind if your partner watched it? How about together vs alone?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
51~ What tends to bring a smile to your face?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
23- What is your dream job? What was it as a child?
44~ Care to share something about yourself that no one else knows about you?
4- For a pet, Cat, dog or other?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
How about if they talk dirty and/or call you names?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
What would you say to prove to yourself that it was really you?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
92~ Everyone needs a “safe” word. What is yours?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What was the longest? What was the shortest?
11~ Have you ever been caught by your parents or children or others while having sex?
10- What is your favorite family tradition? What’s your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Can you Deep Throat? Do you like the taste of yourself?
7-What do I do in bed that drives you wild? How about, what turns you off?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
1- What was your first impression of me? Has it changed?
Do you think this brought you closer together?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
13~ Is there a difference between, making love, having sex, and fucking?
3- Should Pluto still be considered a planet? 4- How about smoking?
65~ Describe the best orgasm you’ve ever had? Care to share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What do you dislike about me? I asked you to be 100% honest.
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?
11- What's your favorite restaurant? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
30~ What's something unexpected that turns you on?
The Ice Breaker Questions
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Do you like it when they show and tell you what they want?
How many times do you think you have “made love”?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
*** What’s Your Favorite…? ***
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
9- What’s your favorite season and why? What’s your least favorite?
Any that are a turn off?
51~ Are you willing to play adult games with your partner?
9- If you could have three wishes, what would they be? Why?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
Would you ever want to be woken up with oral and/or intercourse?
If you say it, I will stop, and we can talk about it when you are ready.
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
89~ Do you like taking showers together?
1- What’s your favorite animal? Do you a least favorite?
39~ What are your love languages?
Escort/Client Job Applicant/Hiring Manager
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
21~ What was the best date you ever went on? What has been the worst?
33- Beach or Mountains? Or is there another place to like better?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
84~ How do you feel about reading/listening to adult stories?
Would /have you ever given your partner a lap dance and Striptease?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
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?
13- What is the craziest/scariest thing you've ever done?
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
Repairman/Lonely Wife Virgin/Experienced
83~ How do you feel about Porn?
67~ Do you like it when your partner moans and/or is vocal during sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
5~ When you first started having sex, was it what you thought it would be?