What is the most interesting question you can ask to get to know someone?
14.06.2025 08:24
25~ How do you feel about PDA? (Public Display of Affection)
46~ Have you ever used furniture, or other types of things to aid you while having sex?
* Give a rating for each one (0-100)
How will the article end in Part III of Gleissner's hit piece?
Model/Photographer Police/Criminal
11- List at least 5 things on your bucket list. Have you done any of them already?
62~ Have you used adult toys?
10~ How many dates are necessary before you to have sex with someone?
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
When do you feel most peaceful ever?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
81~ Do you have any kinks and/or fetishes?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
How old are you? Male or Female?
33- Beach or Mountains? Or is there another place to like better?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Why does a straight man like anal penetration?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
13- What is the craziest/scariest thing you've ever done?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Why do women consider 80% of men as unattractive?
51~ Are you willing to play adult games with your partner?
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?
15~ Have you ever been “in love”? Who? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
40~ What’s the weirdest place you’ve ever had sex?
13- How about having a certain hair cut/style?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
65~ Describe the best orgasm you’ve ever had? Care to share?
Do you think this Labour Party is qualified to run our country?
*** Deal Breaker Questions ***
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Is there a specific time frame for therapists to tell their clients they are wrong?
Does the thought excite you? Care to share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What’s the worst thing you caught anyone in your family doing?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Over time has your thoughts on sex changed?
Do you think this brought you closer together?
How come Jesus died on Friday and rose on Sunday? That's not 3 days and three nights.
*** Random Questions ***
Do you have a favorite? Is it ok if your partner does?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
U.C. Berkeley's Tiny Pogo Robot has a Unique Locomotion Style - Core77
5- Have you ever been hypnotized? Would you allow yourself to be?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
60~ How important is oral sex? Do you like receiving? Do you like giving?
How many partners have you had oral sex with? Who? Care to Share?
49~ How many times have you been married? Why did they end?
52~ What are your hobbies?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
11- What's your favorite restaurant? What’s your least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
14- What's your favorite dessert? Do you a least favorite?
22- What is your favorite childhood memory? What is your least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
44~ Care to share something about yourself that no one else knows about you?
12- What’s your favorite food? What’s your least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
7- What if a person smells a certain way? 8- How about smoking?
Family Relation Age Play
3- What was the most surprising thing you’ve learned about me throughout our relationship?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
53~ How much can you tell me about the one thing you are most passionate about?
1- What was your first impression of me? Has it changed?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
11~ Have you ever been caught by your parents or children or others while having sex?
83~ How do you feel about Porn?
3- Should Pluto still be considered a planet? 4- How about smoking?
If NO, would you ever have one? Would it be with 2 men or 2 women?
71~ Would you give your partner a hand or foot job? Would you receive one?
21~ What was the best date you ever went on? What has been the worst?
How many times do you think you have “made love”?
19~ Who/when was your first “heartbreak”?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
36- Do you play video games? What is your favorite? Do you a least favorite?
32- What's your greatest talent? Can I see it right now?
The Ice Breaker Questions
26~ What side of the bed do you sleep on?
Would you read them together?
15- What bad habit do you wish you could quit? Do you have any addictions?
(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…)
Escort/Client Job Applicant/Hiring Manager
31- If given a chance to be immortal, would you take it? Why?
6- Do you have dreams? Can you remember them? What do you usually dream about?
89~ Do you like taking showers together?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
20- What’s your favorite candy? What’s your least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
76~ Have you had a threesome? Care to Share?
30~ What's something unexpected that turns you on?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
9- Is there something you’ve always wanted to ask me but you’re afraid?
70~ Would/do you have/like anal sex?
Do you watch it? What is your favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What was the longest? What was the shortest?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
10- List 5 of your top pet peeves.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Doctor/Nurse Stripper/Client
48~ Have you ever paid or been paid for sex?
17- What’s your favorite holiday? What’s your least favorite?
You know that I will be 100% truthful, so ask.
92~ Everyone needs a “safe” word. What is yours?
Do you like it when they show and tell you what they want?
1~ How old were you when you had your first kiss? 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?
18~ Who/when was your first “crush”?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Nothing too Serious
Teacher/Student Stranger/One Night Stand
Any that are a turn off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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…
Can you Deep Throat? Do you like the taste of yourself?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Would you do it again, and would you rather 2 females or 2 males?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
15- What's your favorite saying? What word or phrase is your least favorite?
18- How often do you drink alcohol? What is your favorite drink?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
36~ What is your favorite time of day to have sex/make love?
*** Questions About Me ***
19- What’s your favorite fairytale? What’s your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
9~ How many times over your lifetime do you think you have had sex so far?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
13- What’s your favorite drink? What’s your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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?
3- What Superhero or Superpower would you want to be/have?
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,
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
52~ Are you willing to make “those types” of bets with your partner?
I would allow you to do it… What would you do to me?
Nurse/Patient Celebrity/Fan
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
3- What’s your favorite smell? Do you a least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What would you say to prove to yourself that it was really you?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
8- What are your thoughts on politics?
What have you learned about me that was new and/or surprising?
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?
2- What’s your favorite color? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
61~ How willing would you be to try new sexual positions?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
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…
19- Do/have you smoked? What do you prefer? How often?
37- Do you like your name? If you could change it, what would you change it too?
21- What's your favorite way to spend a weekend or time off?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
51~ What tends to bring a smile to your face?
9- What’s your favorite season and why? What’s your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
If you win, what will you make them do?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
34- Ever been to a concert? What was your favorite? Who would you like to see?
4- For a pet, Cat, dog or other?
What do you dislike about me? I asked you to be 100% honest.
What is your favorite toy? Ever wanted to try a specific toy?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
23- What is your dream job? What was it as a child?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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)
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?
Repairman/Lonely Wife Virgin/Experienced
17- Have you ever done drugs? Which ones? How often?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
34~ Do you like the lights on or off during sex?
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
7- What are your thoughts on religion? Is there an afterlife?
80~ Share your top three fantasies/desires. (Be detailed) 😊
29- How superstitious are you?
82~ Do you have any fantasies involving Role-Playing?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
7-What do I do in bed that drives you wild? How about, what turns you off?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Would you mind if your partner watched it? How about together vs alone?
If yes, what?
If you say it, I will stop, and we can talk about it when you are ready.
Have you ever? Care to Share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Do you like the “69” position? Do you prefer to be on top or bottom?
42~ What’s your biggest regret in life?
92~ Have you ever had or have an STD? How many? What was it?
Would you allow me to clean every part of your body with my soapy hands and fingers?
28- What are some things that people do that irritate you?
*** Questions about Relationships/Past ***
What is your favorite position? Why?
Master/Slave Boss/Maid
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.
What have you learned about yourself that you did not before this?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Any that are a turn off?
What is your view on sex? Meaning, When/Where/ How often/
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
48~ Do you have any siblings? Are you close to your family?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
13~ Is there a difference between, making love, having sex, and fucking?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Would you ever want to be woken up with oral and/or intercourse?
10- What is your favorite family tradition? What’s your least favorite?
Please share Did you stop?
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?
Get this wrong and this could mean the end… :-) some funny, some not…
How about if they talk dirty and/or call you names?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
47~ What would be your dream job and why?
*** What’s Your Favorite…? ***
5~ When you first started having sex, was it what you thought it would be?
27- What was/ is nickname? Does it have a meaning behind it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
50~ How many children do you have? What are their ages?
How well do you know me? And some of your thoughts about me
39~ What are your love languages?
That one or two things that made you go hmmmm, OMG or wow!
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
38~ Share your most embarrassing sexual memory?
84~ How do you feel about reading/listening to adult stories?
12- What is the weirdest thing you've ever eaten?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
9- If you could have three wishes, what would they be? Why?
1- What’s your favorite animal? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?