What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 05:06
22- Do you have any birth marks? How about scars? Care to share how you got them?
26~ What side of the bed do you sleep on?
40~ What’s the weirdest place you’ve ever had sex?
Is there anything you did that you regret? If so, what is it, and why?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
81~ Do you have any kinks and/or fetishes?
What is it like to use a Fleshlight?
Teacher/Student Stranger/One Night Stand
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What’s Behind PayPal’s Will Ferrell Ads? - WSJ
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How do you take your erotic photos and how do you choose the poses?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
How does it feel to have sex with a 40 year old curvy aunty?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
9~ How many times over your lifetime do you think you have had sex so far?
52~ What are your hobbies?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
89~ Do you like taking showers together?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Escort/Client Job Applicant/Hiring Manager
Where can I sell naked pics of myself online?
33- Beach or Mountains? Or is there another place to like better?
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?
22- What is your favorite childhood memory? What is your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
*** What’s Your Favorite…? ***
Which city should one visit between Nice and Cannes? Why?
17- Have you ever done drugs? Which ones? How often?
19~ Who/when was your first “heartbreak”?
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?
Do women like watching men sucking men?
Would you allow me to clean every part of your body with my soapy hands and fingers?
92~ Have you ever had or have an STD? How many? What was it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Renault CEO and architect of Alpine F1 project stepping down - The Race
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
34~ Do you like the lights on or off during sex?
Can you explain the meaning of "mint condition" in relation to antiques or collectibles?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
49~ How many times have you been married? Why did they end?
12- What is the weirdest thing you've ever eaten?
Have you ever had a bad gut feeling about someone and it was right?
15- What's your favorite saying? What word or phrase is your least favorite?
48~ Do you have any siblings? Are you close to your family?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
10- List 5 of your top pet peeves.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
21~ What was the best date you ever went on? What has been the worst?
18- How often do you drink alcohol? What is your favorite drink?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
9- What’s your favorite season and why? What’s your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
2- What’s your favorite color? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
29- How superstitious are you?
That one or two things that made you go hmmmm, OMG or wow!
3- Should Pluto still be considered a planet? 4- How about smoking?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
47~ What would be your dream job and why?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Repairman/Lonely Wife Virgin/Experienced
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
17- What’s your favorite holiday? What’s your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
9- If you could have three wishes, what would they be? Why?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
36~ What is your favorite time of day to have sex/make love?
(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…)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
18~ Who/when was your first “crush”?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
82~ Do you have any fantasies involving Role-Playing?
Doctor/Nurse Stripper/Client
You know that I will be 100% truthful, so ask.
7-What do I do in bed that drives you wild? How about, what turns you off?
*** Questions About Me ***
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Over time has your thoughts on sex changed?
13~ Is there a difference between, making love, having sex, and fucking?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
5- Have you ever been hypnotized? Would you allow yourself to be?
Would /have you ever given your partner a lap dance and Striptease?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
What was the longest? What was the shortest?
Do you think this brought you closer together?
33- If you could visit any time period, when would you pick? Please explain why?
Nothing too Serious
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
13- What is the craziest/scariest thing you've ever done?
Any that are a turn off?
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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
8- What are your thoughts on politics?
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…
Prisoner/Prison Guard Landlord/Tenant
How well do you know me? And some of your thoughts about me
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
If YES, was it with 2 men or 2 women? Did you enjoy it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How old are you? Male or Female?
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?
10~ How many dates are necessary before you to have sex with someone?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
76~ Have you had a threesome? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
60~ How important is oral sex? Do you like receiving? Do you like giving?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
7- What are your thoughts on religion? Is there an afterlife?
15- What bad habit do you wish you could quit? Do you have any addictions?
80~ Share your top three fantasies/desires. (Be detailed) 😊
I would allow you to do it… What would you do to me?
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Would you read them together?
23- What is your dream job? What was it as a child?
What is your favorite position? Why?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Does the thought excite you? Care to share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
28~ What are some things that turn on? What is your biggest turn on?
61~ How willing would you be to try new sexual positions?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear 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?
Family Relation Age Play
19- What’s your favorite fairytale? What’s your least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
9- Is there something you’ve always wanted to ask me but you’re afraid?
38~ Share your most embarrassing sexual memory?
31- If given a chance to be immortal, would you take it? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What have you learned about yourself that you did not before this?
4- For a pet, Cat, dog or other?
How about if they talk dirty and/or call you names?
What have you learned about me that was new and/or surprising?
Would you ever want to be woken up with oral and/or intercourse?
51~ What tends to bring a smile to your face?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Will you cheat again? How can, you be sure? Define what cheating is to you.
32- What's your greatest talent? Can I see it right now?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
10- What is your favorite family tradition? What’s your least favorite?
Do you watch it? What is your favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
37- Do you like your name? If you could change it, what would you change it too?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
7- What if a person smells a certain way? 8- How about smoking?
*** Deal Breaker Questions ***
If NO, would you ever have one? Would it be with 2 men or 2 women?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
92~ Everyone needs a “safe” word. What is yours?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
83~ How do you feel about Porn?
70~ Would/do you have/like anal sex?
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,
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
13- How about having a certain hair cut/style?
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?
What do you dislike about me? I asked you to be 100% honest.
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
3- What’s your favorite smell? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
36- Do you play video games? What is your favorite? Do you a least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
12- What’s your favorite food? What’s your least favorite?
* Give a rating for each one (0-100)
30~ What's something unexpected that turns you on?
20- What’s your favorite candy? What’s your least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
1~ How old were you when you had your first kiss? Who? Care to Share?
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)
11- What's your favorite restaurant? What’s your least favorite?
If you win, what will you make them do?
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?
71~ Would you give your partner a hand or foot job? Would you receive one?
14- What's your favorite dessert? Do you a least favorite?
Master/Slave Boss/Maid
How many times do you think you have “made love”?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
How many partners have you had oral sex with? Who? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
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…
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
*** Questions about Relationships/Past ***
28- What are some things that people do that irritate you?
Would you do it again, and would you rather 2 females or 2 males?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
39~ What are your love languages?
The Ice Breaker Questions
50~ How many children do you have? What are their ages?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
3- What Superhero or Superpower would you want to be/have?
What is your view on sex? Meaning, When/Where/ How often/
14- What is an embarrassing moment in your life? How about your most embarrassing?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
What would you say to prove to yourself that it was really you?
13- What’s your favorite drink? What’s your least favorite?
48~ Have you ever paid or been paid for sex?
Get this wrong and this could mean the end… :-) some funny, some not…
1- What was your first impression of me? Has it changed?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
If yes, what?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
Any that are a turn off?
Nurse/Patient Celebrity/Fan
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
21- What's your favorite way to spend a weekend or time off?
Please share Did you stop?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
42~ What’s your biggest regret in life?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
1- What’s your favorite animal? Do you a least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
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?
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?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
Have you ever? Care to Share?
Model/Photographer Police/Criminal
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
62~ Have you used adult toys?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Do you like it when they show and tell you what they want?
*** Random Questions ***
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
25~ How do you feel about PDA? (Public Display of Affection)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
44~ Care to share something about yourself that no one else knows about you?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Do you have a favorite? Is it ok if your partner does?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
51~ Are you willing to play adult games with your partner?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
8- What's your favorite flavor of ice cream? Do you a least favorite?
84~ How do you feel about reading/listening to adult stories?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
41~ Are there moments in your past that you would want to change? Please share 3 of them.
11- How about if they like a certain sports team? 12-How about drinking too much?