What is the most interesting question you can ask to get to know someone?
08.06.2025 00:22
34- Ever been to a concert? What was your favorite? Who would you like to see?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Why are FtM trans just another type of woman?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
62~ Have you used adult toys?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Get this wrong and this could mean the end… :-) some funny, some not…
If NO, would you ever have one? Would it be with 2 men or 2 women?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Has a cop ever said something to you which was completely unexpected?
3- What Superhero or Superpower would you want to be/have?
36~ What is your favorite time of day to have sex/make love?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Can anyone show a photo with a penis in their anus?
Nothing too Serious
11~ Have you ever been caught by your parents or children or others while having 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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
‘Stranger Things’ Season 5 Gets Three-Part Release, Series Finale Set for New Year’s Eve - Variety
30~ What's something unexpected that turns you on?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
33- If you could visit any time period, when would you pick? Please explain why?
Is the Democrat party connected with organized crime in America?
28- What are some things that people do that irritate you?
83~ How do you feel about Porn?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Solar 'cannonballs' may have stripped Mars of its water, long-awaited study reveals - Live Science
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)
29- How superstitious are you?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
18~ Who/when was your first “crush”?
52~ What are your hobbies?
48~ Do you have any siblings? Are you close to your family?
The Ice Breaker Questions
Master/Slave Boss/Maid
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Would you ever want to be woken up with oral and/or intercourse?
52~ Are you willing to make “those types” of bets with your partner?
How many times do you think you have “made love”?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
22- What is your favorite childhood memory? What is your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
3- What’s your favorite smell? Do you a least favorite?
Please share Did you stop?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Doctor/Nurse Stripper/Client
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
14- What's your favorite dessert? Do you a least favorite?
What was the longest? What was the shortest?
17- Have you ever done drugs? Which ones? How often?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
14- What is an embarrassing moment in your life? How about your most embarrassing?
Would you read them together?
Do you have a favorite? Is it ok if your partner does?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
71~ Would you give your partner a hand or foot job? Would you receive one?
I would allow you to do it… What would you do to me?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
*** Random Questions ***
15~ Have you ever been “in love”? Who? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
Prisoner/Prison Guard Landlord/Tenant
51~ Are you willing to play adult games with your partner?
What would you say to prove to yourself that it was really you?
13- What is the craziest/scariest thing you've ever done?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Do you like the “69” position? Do you prefer to be on top or bottom?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Have you ever? Care to Share?
(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…)
15- What's your favorite saying? What word or phrase is your least favorite?
9- What’s your favorite season and why? What’s your least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
50~ How many children do you have? What are their ages?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Repairman/Lonely Wife Virgin/Experienced
7- What are your thoughts on religion? Is there an afterlife?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
2- What’s your favorite color? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
How well do you know me? And some of your thoughts about me
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
* Give a rating for each one (0-100)
92~ Have you ever had or have an STD? How many? What was it?
25~ How do you feel about PDA? (Public Display of Affection)
What do you dislike about me? I asked you to be 100% honest.
Does the thought excite you? Care to share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
36- Do you play video games? What is your favorite? Do you a least favorite?
Over time has your thoughts on sex changed?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
18- How often do you drink alcohol? What is your favorite drink?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Do you like it when they show and tell you what they want?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Would /have you ever given your partner a lap dance and Striptease?
8- What's your favorite flavor of ice cream? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Do you think this brought you closer together?
Escort/Client Job Applicant/Hiring Manager
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
42~ What’s your biggest regret in life?
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?
49~ How many times have you been married? Why did they end?
22- Do you have any birth marks? How about scars? Care to share how you got them?
What have you learned about yourself that you did not before this?
10~ How many dates are necessary before you to have sex with someone?
3- Should Pluto still be considered a planet? 4- How about smoking?
51~ What tends to bring a smile to your face?
82~ Do you have any fantasies involving Role-Playing?
9~ How many times over your lifetime do you think you have had sex so far?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Any that are a turn off?
What have you learned about me that was new and/or surprising?
53~ How much can you tell me about the one thing you are most passionate about?
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?
65~ Describe the best orgasm you’ve ever had? Care to share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
*** Deal Breaker Questions ***
67~ Do you like it when your partner moans and/or is vocal during sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
How many partners have you had oral sex with? Who? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
*** Questions About Me ***
84~ How do you feel about reading/listening to adult stories?
31- If given a chance to be immortal, would you take it? Why?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Can you Deep Throat? Do you like the taste of yourself?
Would you do it again, and would you rather 2 females or 2 males?
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?
32- What's your greatest talent? Can I see it right now?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
37- Do you like your name? If you could change it, what would you change it too?
70~ Would/do you have/like anal sex?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
7-What do I do in bed that drives you wild? How about, what turns you off?
Any that are a turn off?
40~ What’s the weirdest place you’ve ever had sex?
81~ Do you have any kinks and/or fetishes?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
12- What is the weirdest thing you've ever eaten?
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…
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
22~ What is the best pickup line anyone has ever used on you? What was the worst?
13- What’s your favorite drink? What’s your least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
11- List at least 5 things on your bucket list. Have you done any of them already?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
If you win, what will you make them do?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
21~ What was the best date you ever went on? What has been the worst?
80~ Share your top three fantasies/desires. (Be detailed) 😊
61~ How willing would you be to try new sexual positions?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
47~ What would be your dream job and why?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
26~ What side of the bed do you sleep on?
What is your favorite position? Why?
You know that I will be 100% truthful, so ask.
8- What are your thoughts on politics?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
12- What’s your favorite food? What’s your least favorite?
38~ Share your most embarrassing sexual memory?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would you mind if your partner watched it? How about together vs alone?
17- What’s your favorite holiday? What’s your least favorite?
1- What was your first impression of me? Has it changed?
44~ Care to share something about yourself that no one else knows about you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
11- How about if they like a certain sports team? 12-How about drinking too much?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
23- What is your dream job? What was it as a child?
*** What’s Your Favorite…? ***
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
11- What's your favorite restaurant? What’s your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
1- What’s your favorite animal? Do you a least favorite?
13- How about having a certain hair cut/style?
Family Relation Age Play
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
60~ How important is oral sex? Do you like receiving? Do you like giving?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
What is your view on sex? Meaning, When/Where/ How often/
*** Questions about Relationships/Past ***
How about if they talk dirty and/or call you names?
4- For a pet, Cat, dog or other?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
If yes, what?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
34~ Do you like the lights on or off during sex?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
7- What if a person smells a certain way? 8- How about smoking?
92~ Everyone needs a “safe” word. What is yours?
10- List 5 of your top pet peeves.
Teacher/Student Stranger/One Night Stand
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?
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,
9- If you could have three wishes, what would they be? Why?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
76~ Have you had a threesome? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
9- Is there something you’ve always wanted to ask me but you’re afraid?
48~ Have you ever paid or been paid for sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
How old are you? Male or Female?
19- What’s your favorite fairytale? What’s your least favorite?
That one or two things that made you go hmmmm, OMG or wow!
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?
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?
89~ Do you like taking showers together?
45~ How do you feel about me blindfolding you? How about blindfolding me?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
1~ How old were you when you had your first kiss? Who? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
Nurse/Patient Celebrity/Fan
41~ Are there moments in your past that you would want to change? Please share 3 of them.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
10- What is your favorite family tradition? What’s your least favorite?
19~ Who/when was your first “heartbreak”?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
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
27- What was/ is nickname? Does it have a meaning behind it?
Do you watch it? What is your favorite?
21- What's your favorite way to spend a weekend or time off?
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…
20- What’s your favorite candy? What’s your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
5- Have you ever been hypnotized? Would you allow yourself to be?
What is your favorite toy? Ever wanted to try a specific toy?
39~ What are your love languages?
19- Do/have you smoked? What do you prefer? How often?