What is the most interesting question you can ask to get to know someone?
08.06.2025 03:50
44~ Care to share something about yourself that no one else knows about you?
Prisoner/Prison Guard Landlord/Tenant
17- What’s your favorite holiday? What’s your least favorite?
Anycubic has yet another sale happening, and the 3D printer I own is $200 off - Creative Bloq
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?
27- What was/ is nickname? Does it have a meaning behind it?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
What would it take for you to consider yourself a "Swiftie" like Flavor Flav?
Please share Did you stop?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
14- What is an embarrassing moment in your life? How about your most embarrassing?
New model helps to figure out which distant planets may host life - Phys.org
1- What’s your favorite animal? Do you a least favorite?
10~ How many dates are necessary before you to have sex with someone?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What are some signs that a therapist may have poor boundaries with their clients?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
I would allow you to do it… What would you do to me?
You know that I will be 100% truthful, so ask.
How is TikTok able to censor porn?
53~ How much can you tell me about the one thing you are most passionate about?
Escort/Client Job Applicant/Hiring Manager
11- What's your favorite restaurant? What’s your least favorite?
Why do humans sweat while stressed?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Do you have a favorite? Is it ok if your partner does?
What would TERFs do if there weren't such a thing as being transgender? Who would be their target?
20- What’s your favorite candy? What’s your least favorite?
18~ Who/when was your first “crush”?
80~ Share your top three fantasies/desires. (Be detailed) 😊
50~ How many children do you have? What are their ages?
If yes, what?
21- What's your favorite way to spend a weekend or time off?
How much stronger is an average man than an average woman?
52~ What are your hobbies?
Teacher/Student Stranger/One Night Stand
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Bethenny Frankel Reveals Her Teenage Daughter Bryn's Reaction to Her SI Swimsuit Look - People.com
(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…)
How about if they talk dirty and/or call you names?
3- What’s your favorite smell? Do you a least favorite?
This brilliant, hidden iPhone feature lets you print anything to PDF - Boy Genius Report
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
12- What’s your favorite food? What’s your least favorite?
23- What is your dream job? What was it as a child?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Will you cheat again? How can, you be sure? Define what cheating is to you.
49~ How many times have you been married? Why did they end?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
14- What's your favorite dessert? Do you a 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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
3- What Superhero or Superpower would you want to be/have?
8- What's your favorite flavor of ice cream? Do you a least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
29- How superstitious are you?
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?
61~ How willing would you be to try new sexual positions?
How many partners have you had oral sex with? Who? Care to Share?
48~ Have you ever paid or been paid for sex?
42~ What’s your biggest regret in life?
28~ What are some things that turn on? What is your biggest turn on?
51~ What tends to bring a smile to your face?
29~ What are some things that turn you off? What is your biggest turn off?
What would you say to prove to yourself that it was really you?
31- If given a chance to be immortal, would you take it? Why?
60~ How important is oral sex? Do you like receiving? Do you like giving?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
33- Beach or Mountains? Or is there another place to like better?
1- What was your first impression of me? Has it changed?
9- If you could have three wishes, what would they be? Why?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
70~ Would/do you have/like anal sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
18- How often do you drink alcohol? What is your favorite drink?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
* Give a rating for each one (0-100)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
That one or two things that made you go hmmmm, OMG or wow!
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Master/Slave Boss/Maid
15~ Have you ever been “in love”? Who? Care to Share?
Nothing too Serious
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
40~ What’s the weirdest place you’ve ever had sex?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
9~ How many times over your lifetime do you think you have had sex so far?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
15- What's your favorite saying? What word or phrase is your least favorite?
76~ Have you had a threesome? Care to Share?
*** Random Questions ***
28- What are some things that people do that irritate you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Any that are a turn off?
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?
10- List 5 of your top pet peeves.
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
30~ What's something unexpected that turns you on?
11- List at least 5 things on your bucket list. Have you done any of them already?
Do you watch it? What is your favorite?
13- What is the craziest/scariest thing you've ever done?
92~ Everyone needs a “safe” word. What is yours?
22- What is your favorite childhood memory? What is your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
If NO, would you ever have one? Would it be with 2 men or 2 women?
26~ What side of the bed do you sleep on?
62~ Have you used adult toys?
36~ What is your favorite time of day to have sex/make love?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
2- What’s your favorite color? Do you a least favorite?
8- What are your thoughts on politics?
5~ When you first started having sex, was it what you thought it would be?
What is your favorite position? Why?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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,
Do you think this brought you closer together?
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…
What was the longest? What was the shortest?
What is your view on sex? Meaning, When/Where/ How often/
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
19- Do/have you smoked? What do you prefer? How often?
What is your favorite toy? Ever wanted to try a specific toy?
19- What’s your favorite fairytale? What’s your least favorite?
What do you dislike about me? I asked you to be 100% honest.
Would you ever want to be woken up with oral and/or intercourse?
How well do you know me? And some of your thoughts about me
7-What do I do in bed that drives you wild? How about, what turns you off?
39~ What are your love languages?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
81~ Do you have any kinks and/or fetishes?
82~ Do you have any fantasies involving Role-Playing?
33- If you could visit any time period, when would you pick? Please explain why?
Get this wrong and this could mean the end… :-) some funny, some not…
7- What if a person smells a certain way? 8- How about smoking?
5- Have you ever been hypnotized? Would you allow yourself to be?
38~ Share your most embarrassing sexual memory?
Any that are a turn off?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
How old are you? Male or Female?
34~ Do you like the lights on or off during sex?
13- What’s your favorite drink? What’s your least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
92~ Have you ever had or have an STD? How many? What was it?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
83~ How do you feel about Porn?
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…
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
12- What is the weirdest thing you've ever eaten?
Model/Photographer Police/Criminal
Have you ever? Care to Share?
*** Questions about Relationships/Past ***
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
84~ How do you feel about reading/listening to adult stories?
19~ Who/when was your first “heartbreak”?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Would you mind if your partner watched it? How about together vs alone?
52~ Are you willing to make “those types” of bets with your partner?
17- Have you ever done drugs? Which ones? How often?
3- Should Pluto still be considered a planet? 4- How about smoking?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
1~ How old were you when you had your first kiss? Who? Care to Share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
21~ What was the best date you ever went on? What has been the worst?
Doctor/Nurse Stripper/Client
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Can you Deep Throat? Do you like the taste of yourself?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
22- Do you have any birth marks? How about scars? Care to share how you got them?
What have you learned about me that was new and/or surprising?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
45~ How do you feel about me blindfolding you? How about blindfolding me?
10- What is your favorite family tradition? What’s your least favorite?
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?
67~ Do you like it when your partner moans and/or is vocal during sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
4- For a pet, Cat, dog or other?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
How many times do you think you have “made love”?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
*** Questions About Me ***
Would /have you ever given your partner a lap dance and Striptease?
If you win, what will you make them do?
25~ How do you feel about PDA? (Public Display of Affection)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
89~ Do you like taking showers together?
What have you learned about yourself that you did not before this?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
37- Do you like your name? If you could change it, what would you change it too?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
36- Do you play video games? What is your favorite? Do you a 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)
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Over time has your thoughts on sex changed?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you like it when they show and tell you what they want?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
48~ Do you have any siblings? Are you close to your family?
9- What’s your favorite season and why? What’s your least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Family Relation Age Play
47~ What would be your dream job and why?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Would you allow me to clean every part of your body with my soapy hands and fingers?
*** What’s Your Favorite…? ***
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
65~ Describe the best orgasm you’ve ever had? Care to share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Nurse/Patient Celebrity/Fan
51~ Are you willing to play adult games with your partner?
*** Deal Breaker Questions ***
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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?
Repairman/Lonely Wife Virgin/Experienced
If you say it, I will stop, and we can talk about it when you are ready.
Does the thought excite you? Care to share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
The Ice Breaker Questions
13~ Is there a difference between, making love, having sex, and fucking?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
13- How about having a certain hair cut/style?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Would you do it again, and would you rather 2 females or 2 males?
Do you like the “69” position? Do you prefer to be on top or bottom?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
If YES, was it with 2 men or 2 women? Did you enjoy it?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
9- Is there something you’ve always wanted to ask me but you’re afraid?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
11- How about if they like a certain sports team? 12-How about drinking too much?
32- What's your greatest talent? Can I see it right now?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Would you read them together?