What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 16:19
53~ How much can you tell me about the one thing you are most passionate about?
Teacher/Student Stranger/One Night Stand
What have you learned about me that was new and/or surprising?
What are some reasons why some men choose to live alone instead of getting married?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
12- What’s your favorite food? What’s your least favorite?
14- What's your favorite dessert? Do you a least favorite?
Why do men first look at a woman's chest instead of their face?
12- What is the weirdest thing you've ever eaten?
Any that are a turn off?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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 board or cards game? What is your favorite? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
Will Miami’s latest effort at “culture change” work? - NBC Sports
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Nurse/Patient Celebrity/Fan
80~ Share your top three fantasies/desires. (Be detailed) 😊
Why did Kakashi use Chidori against Rin, despite knowing about her feelings for Obito?
89~ Do you like taking showers together?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What type of crossdresser are you?
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?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
29- How superstitious are you?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Why does my penis look like a mushroom when it gets big?
42~ What’s your biggest regret in life?
Any that are a turn off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What made you stop being an addict?
48~ Have you ever paid or been paid for sex?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
What would you do if you were lost at sea in the Florida Keys?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
*** What’s Your Favorite…? ***
Teens like me, what are your expectations when entering adulthood?
19- Do/have you smoked? What do you prefer? How often?
45~ How do you feel about me blindfolding you? How about blindfolding me?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
60~ How important is oral sex? Do you like receiving? Do you like giving?
38~ Share your most embarrassing sexual memory?
That one or two things that made you go hmmmm, OMG or wow!
Why do unattractive men assume that a pretty woman like me want them?
1~ How old were you when you had your first kiss? Who? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
9- What’s your favorite season and why? What’s your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Does the thought excite you? Care to share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
34- Ever been to a concert? What was your favorite? Who would you like to see?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How many times do you think you have “made love”?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
15- What bad habit do you wish you could quit? Do you have any addictions?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Over time has your thoughts on sex changed?
76~ Have you had a threesome? Care to Share?
49~ How many times have you been married? Why did they end?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
8- What are your thoughts on politics?
What have you learned about yourself that you did not before this?
50~ How many children do you have? What are their ages?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Repairman/Lonely Wife Virgin/Experienced
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
14- What is an embarrassing moment in your life? How about your most embarrassing?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
9~ How many times over your lifetime do you think you have had sex so far?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
71~ Would you give your partner a hand or foot job? Would you receive one?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
How many partners have you had oral sex with? Who? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
5~ When you first started having sex, was it what you thought it would be?
Do you watch it? What is your favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
33- Beach or Mountains? Or is there another place to like better?
33- If you could visit any time period, when would you pick? Please explain why?
Can you Deep Throat? Do you like the taste of yourself?
How well do you know me? And some of your thoughts about me
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?
1- What was your first impression of me? Has it changed?
I would allow you to do it… What would you do to me?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Have you ever? Care to Share?
Family Relation Age Play
19- What’s your favorite fairytale? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
Nothing too Serious
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Doctor/Nurse Stripper/Client
62~ Have you used adult toys?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Do you think this brought you closer together?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What was the longest? What was the shortest?
The Ice Breaker Questions
1- What’s your favorite animal? Do you a least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
9- If you could have three wishes, what would they be? Why?
3- Should Pluto still be considered a planet? 4- How about smoking?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Do you have a favorite? Is it ok if your partner does?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How about if they talk dirty and/or call you names?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
7- What if a person smells a certain way? 8- How about smoking?
15- What's your favorite saying? What word or phrase is your least favorite?
92~ Have you ever had or have an STD? How many? What was it?
Do you like the “69” position? Do you prefer to be on top or bottom?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
83~ How do you feel about Porn?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
* Give a rating for each one (0-100)
36~ What is your favorite time of day to have sex/make love?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
52~ Are you willing to make “those types” of bets with your partner?
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?
If you win, what will you make them do?
28- What are some things that people do that irritate you?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? 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)
How old are you? Male or Female?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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
65~ Describe the best orgasm you’ve ever had? Care to share?
17- What’s your favorite holiday? What’s your least favorite?
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…
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
17- Have you ever done drugs? Which ones? How often?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
13- What’s your favorite drink? What’s your least favorite?
2- What’s your favorite color? Do you a least favorite?
18~ Who/when was your first “crush”?
Please share Did you stop?
34~ Do you like the lights on or off during sex?
If yes, what?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
47~ What would be your dream job and why?
(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…)
84~ How do you feel about reading/listening to adult stories?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
11- What's your favorite restaurant? What’s your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
Prisoner/Prison Guard Landlord/Tenant
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
7-What do I do in bed that drives you wild? How about, what turns you 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?
*** Questions about Relationships/Past ***
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?
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?
Would /have you ever given your partner a lap dance and Striptease?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
37- Do you like your name? If you could change it, what would you change it too?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
4- For a pet, Cat, dog or other?
10- List 5 of your top pet peeves.
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?
52~ What are your hobbies?
44~ Care to share something about yourself that no one else knows about you?
Would you mind if your partner watched it? How about together vs alone?
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,
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
13- How about having a certain hair cut/style?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
*** Questions About Me ***
13~ Is there a difference between, making love, having sex, and fucking?
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?
21~ What was the best date you ever went on? What has been the worst?
26~ What side of the bed do you sleep on?
*** Random Questions ***
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
61~ How willing would you be to try new sexual positions?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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.
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?
10- What is your favorite family tradition? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
18- How often do you drink alcohol? What is your favorite drink?
48~ Do you have any siblings? Are you close to your family?
*** Deal Breaker Questions ***
What do you dislike about me? I asked you to be 100% honest.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Model/Photographer Police/Criminal
81~ Do you have any kinks and/or fetishes?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
3- What’s your favorite smell? Do you a least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
92~ Everyone needs a “safe” word. What is yours?
What is your view on sex? Meaning, When/Where/ How often/
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
If you say it, I will stop, and we can talk about it when you are ready.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
21- What's your favorite way to spend a weekend or time off?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
11- How about if they like a certain sports team? 12-How about drinking too much?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Would you read them together?
9- Is there something you’ve always wanted to ask me but you’re afraid?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
51~ Are you willing to play adult games with your partner?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What is your favorite toy? Ever wanted to try a specific toy?
15~ Have you ever been “in love”? Who? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
7- What are your thoughts on religion? Is there an afterlife?
23- What is your dream job? What was it as a child?
28~ What are some things that turn on? What is your biggest turn on?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
30~ What's something unexpected that turns you on?
39~ What are your love languages?
32- What's your greatest talent? Can I see it right now?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
51~ What tends to bring a smile to your face?
Would you do it again, and would you rather 2 females or 2 males?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
70~ Would/do you have/like anal sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
67~ Do you like it when your partner moans and/or is vocal during sex?
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)
10~ How many dates are necessary before you to have sex with someone?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What is your favorite position? Why?
3- What Superhero or Superpower would you want to be/have?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
You know that I will be 100% truthful, so ask.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
22- Do you have any birth marks? How about scars? Care to share how you got them?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
25~ How do you feel about PDA? (Public Display of Affection)
40~ What’s the weirdest place you’ve ever had sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
What would you say to prove to yourself that it was really you?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you like it when they show and tell you what they want?
36- Do you play video games? What is your favorite? Do you a least favorite?
19~ Who/when was your first “heartbreak”?
82~ Do you have any fantasies involving Role-Playing?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
27- What was/ is nickname? Does it have a meaning behind it?