What is the most interesting question you can ask to get to know someone?
12.06.2025 03:23
Will you cheat again? How can, you be sure? Define what cheating is to you.
18- How often do you drink alcohol? What is your favorite drink?
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…
Escort/Client Job Applicant/Hiring Manager
What do you dislike about me? I asked you to be 100% honest.
62~ Have you used adult toys?
13- What is the craziest/scariest thing you've ever done?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
15~ Have you ever been “in love”? Who? Care to Share?
Why do women consider 80% of men as unattractive?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
I would allow you to do it… What would you do to me?
Model/Photographer Police/Criminal
Why do women have sex with dogs?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
How about if they talk dirty and/or call you names?
What is your favorite position? Why?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
3- What’s your favorite smell? Do you a least favorite?
If you win, what will you make them do?
50~ How many children do you have? What are their ages?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
DF Weekly: Why would Microsoft "sideline" its next generation handheld? - Eurogamer
27- What was/ is nickname? Does it have a meaning behind it?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
13- How about having a certain hair cut/style?
Why do men love boobs (irrespective of big or small)?
28~ What are some things that turn on? What is your biggest turn on?
11- What's your favorite restaurant? What’s your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Sex advice: I'm finally ready to enter my promiscuity era. But there's a catch. - Slate Magazine
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
28- What are some things that people do that irritate you?
89~ Do you like taking showers together?
What have I done wrong? How can I start over?
53~ How much can you tell me about the one thing you are most passionate about?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
11- List at least 5 things on your bucket list. Have you done any of them already?
A hidden 'super-Earth' exoplanet is dipping in and out of its habitable zone - Space
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
24~ What are your expectations in a relationship? (I know a very big question, take your time)
92~ Everyone needs a “safe” word. What is yours?
What are some ways to improve speed in sprinting, running uphill, and long/middle distance running?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
What is the best way to end a relationship with someone who has future plans with you?
52~ Are you willing to make “those types” of bets with your partner?
70~ Would/do you have/like anal sex?
The Ice Breaker Questions
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Why am I so unproductive when it's a holiday the next day?
82~ Do you have any fantasies involving Role-Playing?
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?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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)
*** Random Questions ***
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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,
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
19- Do/have you smoked? What do you prefer? How often?
Do you watch it? What is your favorite?
84~ How do you feel about reading/listening to adult stories?
8- What's your favorite flavor of ice cream? Do you a least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
21- What's your favorite way to spend a weekend or time off?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
17- Have you ever done drugs? Which ones? How often?
If you say it, I will stop, and we can talk about it when you are ready.
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Family Relation Age Play
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
65~ Describe the best orgasm you’ve ever had? Care to share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
5~ When you first started having sex, was it what you thought it would be?
9~ How many times over your lifetime do you think you have had sex so far?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
3- What Superhero or Superpower would you want to be/have?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
52~ What are your hobbies?
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?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
19~ Who/when was your first “heartbreak”?
Doctor/Nurse Stripper/Client
67~ Do you like it when your partner moans and/or is vocal during sex?
45~ How do you feel about me blindfolding you? How about blindfolding me?
56~ Would you ever go to a strip club with your partner? Have you ever been? 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?
*** Questions About Me ***
33- If you could visit any time period, when would you pick? Please explain why?
Would you allow me to clean every part of your body with my soapy hands and fingers?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
92~ Have you ever had or have an STD? How many? What was it?
Can you Deep Throat? Do you like the taste of yourself?
20- What’s your favorite candy? What’s your least favorite?
How many times do you think you have “made love”?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
76~ Have you had a threesome? Care to Share?
42~ What’s your biggest regret in life?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What is your favorite toy? Ever wanted to try a specific toy?
If yes, what?
4- For a pet, Cat, dog or other?
61~ How willing would you be to try new sexual positions?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
26~ What side of the bed do you sleep on?
13~ Is there a difference between, making love, having sex, and fucking?
Prisoner/Prison Guard Landlord/Tenant
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Do you think this brought you closer together?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
17- What’s your favorite holiday? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
34~ Do you like the lights on or off during sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
36~ What is your favorite time of day to have sex/make love?
That one or two things that made you go hmmmm, OMG or wow!
23- What is your dream job? What was it as a child?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** Questions about Relationships/Past ***
Any that are a turn off?
80~ Share your top three fantasies/desires. (Be detailed) 😊
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Master/Slave Boss/Maid
41~ Are there moments in your past that you would want to change? Please share 3 of them.
9- If you could have three wishes, what would they be? Why?
7-What do I do in bed that drives you wild? How about, what turns you off?
22- Do you have any birth marks? How about scars? Care to share how you got them?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Do you have a favorite? Is it ok if your partner does?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
12- What’s your favorite food? What’s your least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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?
21~ What was the best date you ever went on? What has been the worst?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
What was the longest? What was the shortest?
2- What’s your favorite color? Do you a least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
29- How superstitious are you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
9- What’s your favorite season and why? What’s your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
Would you read them together?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Does the thought excite you? Care to share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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?
Nothing too Serious
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
11~ Have you ever been caught by your parents or children or others while having sex?
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?
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…
44~ Care to share something about yourself that no one else knows about you?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
Nurse/Patient Celebrity/Fan
36- Do you play video games? What is your favorite? Do you a least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If NO, would you ever have one? Would it be with 2 men or 2 women?
30~ What's something unexpected that turns you on?
22- What is your favorite childhood memory? What is your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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?
81~ Do you have any kinks and/or fetishes?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
10~ How many dates are necessary before you to have sex with someone?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What have you learned about me that was new and/or surprising?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
48~ Do you have any siblings? Are you close to your family?
(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…)
48~ Have you ever paid or been paid for sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
8- What are your thoughts on politics?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Do you like it when they show and tell you what they want?
1- What’s your favorite animal? Do you a least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
37- Do you like your name? If you could change it, what would you change it too?
47~ What would be your dream job and why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
33- Beach or Mountains? Or is there another place to like better?
1~ How old were you when you had your first kiss? Who? Care to Share?
38~ Share your most embarrassing sexual memory?
83~ How do you feel about Porn?
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
How old are you? Male or Female?
Would /have you ever given your partner a lap dance and Striptease?
25~ How do you feel about PDA? (Public Display of Affection)
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?
Teacher/Student Stranger/One Night Stand
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
32- What's your greatest talent? Can I see it right now?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
You know that I will be 100% truthful, so ask.
10- List 5 of your top pet peeves.
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
*** Deal Breaker Questions ***
12- What is the weirdest thing you've ever eaten?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Over time has your thoughts on sex changed?
Would you ever want to be woken up with oral and/or intercourse?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
51~ Are you willing to play adult games with your partner?
How many partners have you had oral sex with? Who? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
1- What was your first impression of me? Has it changed?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
7- What if a person smells a certain way? 8- How about smoking?
31- If given a chance to be immortal, would you take it? Why?
If YES, was it with 2 men or 2 women? Did you enjoy it?
39~ What are your love languages?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
15- What bad habit do you wish you could quit? Do you have any addictions?
Please share Did you stop?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
13- What’s your favorite drink? What’s your least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Would you do it again, and would you rather 2 females or 2 males?
What would you say to prove to yourself that it was really you?
11- How about if they like a certain sports team? 12-How about drinking too much?
What have you learned about yourself that you did not before this?
Would you mind if your partner watched it? How about together vs alone?
71~ Would you give your partner a hand or foot job? Would you receive one?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
* Give a rating for each one (0-100)
Have you ever? 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.
10- What is your favorite family tradition? What’s your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Repairman/Lonely Wife Virgin/Experienced
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
7- What are your thoughts on religion? Is there an afterlife?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
18~ Who/when was your first “crush”?
3- Should Pluto still be considered a planet? 4- How about smoking?
*** What’s Your Favorite…? ***
How well do you know me? And some of your thoughts about me