What is the most interesting question you can ask to get to know someone?
Last Updated: 28.06.2025 02:54
Can you Deep Throat? Do you like the taste of yourself?
Doctor/Nurse Stripper/Client
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- Should Pluto still be considered a planet? 4- How about smoking?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
6- Do you have dreams? Can you remember them? What do you usually dream about?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
82~ Do you have any fantasies involving Role-Playing?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
34- Ever been to a concert? What was your favorite? Who would you like to see?
1- What’s your favorite animal? Do you a least favorite?
Does whey protein affect the kidneys?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
The Ice Breaker Questions
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
How does cultural debt arise from the Cursor IDE?
31- If given a chance to be immortal, would you take it? Why?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
Any that are a turn off?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
What is the opposite personality type of someone with ASPD (antisocial personality disorder)?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
What do you think is the most powerful line in the song "Non, Je Ne Regrette Rien" by Édith Piaf?
Nurse/Patient Celebrity/Fan
52~ Are you willing to make “those types” of bets with your partner?
Do you like it when they show and tell you what they want?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7- What if a person smells a certain way? 8- How about smoking?
Have you ever? Care to Share?
Can a bride cheat on her groom at a wedding?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
76~ Have you had a threesome? Care to Share?
8- What are your thoughts on politics?
10- What is your favorite family tradition? What’s your least favorite?
How many partners have you had oral sex with? Who? Care to Share?
89~ Do you like taking showers together?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
(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…)
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
27- What was/ is nickname? Does it have a meaning behind it?
53~ How much can you tell me about the one thing you are most passionate about?
33- Beach or Mountains? Or is there another place to like better?
39~ What are your love languages?
70~ Would/do you have/like anal sex?
51~ What tends to bring a smile to your face?
Master/Slave Boss/Maid
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?
*** Deal Breaker Questions ***
You know that I will be 100% truthful, so ask.
9- What’s your favorite season and why? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
* Give a rating for each one (0-100)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
5- Have you ever been hypnotized? Would you allow yourself to be?
92~ Have you ever had or have an STD? How many? What was it?
Would you read them together?
How about if they talk dirty and/or call you names?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Any that are a turn off?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Please share Did you stop?
How old are you? Male or Female?
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)
92~ Everyone needs a “safe” word. What is yours?
18- How often do you drink alcohol? What is your favorite drink?
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?
71~ Would you give your partner a hand or foot job? Would you receive one?
52~ What are your hobbies?
22- What is your favorite childhood memory? What is your least favorite?
17- What’s your favorite holiday? What’s your least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
13~ Is there a difference between, making love, having sex, and fucking?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What do you dislike about me? I asked you to be 100% honest.
What have you learned about yourself that you did not before this?
13- How about having a certain hair cut/style?
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 is your favorite toy? Ever wanted to try a specific toy?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral 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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
If you win, what will you make them do?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
21- What's your favorite way to spend a weekend or time off?
Model/Photographer Police/Criminal
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
What is your view on sex? Meaning, When/Where/ How often/
Do you watch it? What is your favorite?
28~ What are some things that turn on? What is your biggest turn on?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
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…
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
14- What's your favorite dessert? Do you a least favorite?
2- What’s your favorite color? Do you a least favorite?
Teacher/Student Stranger/One Night Stand
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,
If NO, would you ever have one? Would it be with 2 men or 2 women?
17- Have you ever done drugs? Which ones? How often?
*** Random Questions ***
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
81~ Do you have any kinks and/or fetishes?
Prisoner/Prison Guard Landlord/Tenant
12- What is the weirdest thing you've ever eaten?
Repairman/Lonely Wife Virgin/Experienced
15- What's your favorite saying? What word or phrase is your least favorite?
That one or two things that made you go hmmmm, OMG or wow!
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
28- What are some things that people do that irritate you?
9- If you could have three wishes, what would they be? Why?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Family Relation Age Play
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What have you learned about me that was new and/or surprising?
19~ Who/when was your first “heartbreak”?
If you say it, I will stop, and we can talk about it when you are ready.
13- What’s your favorite drink? What’s your least favorite?
32- What's your greatest talent? Can I see it right now?
21~ What was the best date you ever went on? What has been the worst?
83~ How do you feel about Porn?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
36- Do you play video games? What is your favorite? Do you a least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
47~ What would be your dream job and why?
34~ Do you like the lights on or off during sex?
What was the longest? What was the shortest?
15~ Have you ever been “in love”? Who? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
14- What is an embarrassing moment in your life? How about your most embarrassing?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
9- Is there something you’ve always wanted to ask me but you’re afraid?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
84~ How do you feel about reading/listening to adult stories?
Does the thought excite you? Care to share?
Would you do it again, and would you rather 2 females or 2 males?
18~ Who/when was your first “crush”?
11- How about if they like a certain sports team? 12-How about drinking too much?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
*** Questions About Me ***
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
How well do you know me? And some of your thoughts about me
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
7-What do I do in bed that drives you wild? How about, what turns you off?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Nothing too Serious
Will you cheat again? How can, you be sure? Define what cheating is to you.
Would you ever want to be woken up with oral and/or intercourse?
Do you think this brought you closer together?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
60~ How important is oral sex? Do you like receiving? Do you like giving?
I would allow you to do it… What would you do to me?
26~ What side of the bed do you sleep on?
3- What’s your favorite smell? Do you a least favorite?
10~ How many dates are necessary before you to have sex with someone?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
62~ Have you used adult toys?
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?
Escort/Client Job Applicant/Hiring Manager
5~ When you first started having sex, was it what you thought it would be?
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
11- What's your favorite restaurant? What’s your least favorite?
13- What is the craziest/scariest thing you've ever done?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
65~ Describe the best orgasm you’ve ever had? Care to share?
51~ Are you willing to play adult games with your partner?
25~ How do you feel about PDA? (Public Display of Affection)
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
If yes, what?
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?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
11~ Have you ever been caught by your parents or children or others while having sex?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
67~ Do you like it when your partner moans and/or is vocal during sex?
What is your favorite position? Why?
49~ How many times have you been married? Why did they end?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
*** What’s Your Favorite…? ***
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you have a favorite? Is it ok if your partner does?
36~ What is your favorite time of day to have sex/make love?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Over time has your thoughts on sex changed?
58~ Have you ever taken Nude or Hard-core photos and/or videos? 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?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
38~ Share your most embarrassing sexual memory?
48~ Have you ever paid or been paid for sex?
61~ How willing would you be to try new sexual positions?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
33- If you could visit any time period, when would you pick? Please explain why?
37- Do you like your name? If you could change it, what would you change it too?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
11- List at least 5 things on your bucket list. Have you done any of them already?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Would /have you ever given your partner a lap dance and Striptease?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
30~ What's something unexpected that turns you on?
44~ Care to share something about yourself that no one else knows about you?
29~ What are some things that turn you off? What is your biggest turn off?
3- What Superhero or Superpower would you want to be/have?
50~ How many children do you have? What are their ages?
80~ Share your top three fantasies/desires. (Be detailed) 😊
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
29- How superstitious are you?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
22- Do you have any birth marks? How about scars? Care to share how you got them?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
9~ How many times over your lifetime do you think you have had sex so far?
1- What was your first impression of me? Has it changed?
12- What’s your favorite food? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
1~ How old were you when you had your first kiss? Who? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
*** Questions about Relationships/Past ***
If YES, was it with 2 men or 2 women? Did you enjoy it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Would you mind if your partner watched it? How about together vs alone?
23- What is your dream job? What was it as a child?
48~ Do you have any siblings? Are you close to your family?
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How many times do you think you have “made love”?
40~ What’s the weirdest place you’ve ever had sex?
42~ What’s your biggest regret in life?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
4- For a pet, Cat, dog or other?
19- Do/have you smoked? What do you prefer? How often?
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~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
What would you say to prove to yourself that it was really you?
10- List 5 of your top pet peeves.