What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 08:30
How well do you know me? And some of your thoughts about me
34- Ever been to a concert? What was your favorite? Who would you like to see?
45~ How do you feel about me blindfolding you? How about blindfolding me?
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?
*** What’s Your Favorite…? ***
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
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,
39~ What are your love languages?
What is the best reply if your boyfriend asks you,"why do you love me?"
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)
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Master/Slave Boss/Maid
*** Questions about Relationships/Past ***
15- What bad habit do you wish you could quit? Do you have any addictions?
If NO, would you ever have one? Would it be with 2 men or 2 women?
What are 5 ways that can be done by the community to improve the public transport system?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
9- What’s your favorite season and why? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Why are the democrats keep insisting that there are more than two genders?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
20- What’s your favorite candy? What’s your least favorite?
What is the American mobile phone number format?
11~ Have you ever been caught by your parents or children or others while having sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What’s the longest time you gone without having sex, after, having it? How much time between the others?
How can I watch porn on TikTok?
30~ What's something unexpected that turns you on?
82~ Do you have any fantasies involving Role-Playing?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
🌿🌻Why are Meghan and Harry not treated like royalty in the United States anymore?
Would you mind if your partner watched it? How about together vs alone?
26~ What side of the bed do you sleep on?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What topics are okay with you in comics and what topics should be totally off the table?
How about if they talk dirty and/or call you names?
60~ How important is oral sex? Do you like receiving? Do you like giving?
19- What’s your favorite fairytale? What’s your least favorite?
48~ Have you ever paid or been paid for sex?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
12- What is the weirdest thing you've ever eaten?
48~ Do you have any siblings? Are you close to your family?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
22~ What is the best pickup line anyone has ever used on you? What was the worst?
11- How about if they like a certain sports team? 12-How about drinking too much?
Any that are a turn off?
10- What is your favorite family tradition? What’s your least favorite?
14- What's your favorite dessert? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Nothing too Serious
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
32- What's your greatest talent? Can I see it right now?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
52~ What are your hobbies?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
67~ Do you like it when your partner moans and/or is vocal during sex?
13- What’s your favorite drink? What’s your least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
92~ Everyone needs a “safe” word. What is yours?
What is your favorite toy? Ever wanted to try a specific toy?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
17- What’s your favorite holiday? What’s your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
71~ Would you give your partner a hand or foot job? Would you receive one?
47~ What would be your dream job and why?
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?
11- List at least 5 things on your bucket list. Have you done any of them already?
53~ How much can you tell me about the one thing you are most passionate about?
14- What is an embarrassing moment in your life? How about your most embarrassing?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
38~ Share your most embarrassing sexual memory?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Doctor/Nurse Stripper/Client
37- Do you like your name? If you could change it, what would you change it too?
The Ice Breaker Questions
How many partners have you had oral sex with? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
51~ Are you willing to play adult games with your partner?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Prisoner/Prison Guard Landlord/Tenant
84~ How do you feel about reading/listening to adult stories?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
23- What is your dream job? What was it as a child?
Model/Photographer Police/Criminal
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
92~ Have you ever had or have an STD? How many? What was it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
22- What is your favorite childhood memory? What is your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What is your favorite position? Why?
What was the longest? What was the shortest?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
50~ How many children do you have? What are their ages?
25~ How do you feel about PDA? (Public Display of Affection)
7- What are your thoughts on religion? Is there an afterlife?
12- What’s your favorite food? What’s your least favorite?
Would you read them together?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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…
If yes, what?
Do you like it when they show and tell you what they want?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
1~ How old were you when you had your first kiss? Who? Care to Share?
How old are you? Male or Female?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
15~ Have you ever been “in love”? Who? Care to Share?
Have you ever? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
62~ Have you used adult toys?
19- Do/have you smoked? What do you prefer? How often?
Nurse/Patient Celebrity/Fan
81~ Do you have any kinks and/or fetishes?
51~ What tends to bring a smile to your face?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
36~ What is your favorite time of day to have sex/make love?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
What have you learned about yourself that you did not before this?
* Give a rating for each one (0-100)
29- How superstitious are you?
5~ When you first started having sex, was it what you thought it would be?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What would you say to prove to yourself that it was really you?
52~ Are you willing to make “those types” of bets with your partner?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
21~ What was the best date you ever went on? What has been the worst?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
You know that I will be 100% truthful, so ask.
49~ How many times have you been married? Why did they end?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
76~ Have you had a threesome? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Do you watch it? What is your favorite?
13- How about having a certain hair cut/style?
*** Random Questions ***
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
18~ Who/when was your first “crush”?
I would allow you to do it… What would you do to me?
83~ How do you feel about Porn?
Over time has your thoughts on sex changed?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Get this wrong and this could mean the end… :-) some funny, some not…
19~ Who/when was your first “heartbreak”?
40~ What’s the weirdest place you’ve ever had 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?
Family Relation Age Play
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
21- What's your favorite way to spend a weekend or time off?
Teacher/Student Stranger/One Night Stand
33- If you could visit any time period, when would you pick? Please explain why?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
Any that are a turn off?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Would you do it again, and would you rather 2 females or 2 males?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you think this brought you closer together?
What have you learned about me that was new and/or surprising?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
70~ Would/do you have/like anal sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
9- Is there something you’ve always wanted to ask me but you’re afraid?
13~ Is there a difference between, making love, having sex, and fucking?
2- What’s your favorite color? Do you a least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
3- What’s your favorite smell? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
27- What was/ is nickname? Does it have a meaning behind it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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…
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What is your view on sex? Meaning, When/Where/ How often/
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Would you allow me to clean every part of your body with my soapy hands and fingers?
3- Should Pluto still be considered a planet? 4- How about smoking?
28- What are some things that people do that irritate you?
31- If given a chance to be immortal, would you take it? Why?
*** Deal Breaker Questions ***
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
42~ What’s your biggest regret in life?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
29~ What are some things that turn you off? What is your biggest turn off?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
44~ Care to share something about yourself that no one else knows about you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
15- What's your favorite saying? What word or phrase is your least favorite?
Escort/Client Job Applicant/Hiring Manager
33- Beach or Mountains? Or is there another place to like better?
9- If you could have three wishes, what would they be? Why?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
28~ What are some things that turn on? What is your biggest turn on?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
7-What do I do in bed that drives you wild? How about, what turns you off?
13- What is the craziest/scariest thing you've ever done?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
17- Have you ever done drugs? Which ones? How often?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
8- What are your thoughts on politics?
Would you ever want to be woken up with oral and/or intercourse?
Do you like the “69” position? Do you prefer to be on top or bottom?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would /have you ever given your partner a lap dance and Striptease?
80~ Share your top three fantasies/desires. (Be detailed) 😊
1- What was your first impression of me? Has it changed?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
3- What Superhero or Superpower would you want to be/have?
Please share Did you stop?
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?
What do you dislike about me? I asked you to be 100% honest.
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
61~ How willing would you be to try new sexual positions?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
(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…)
7- What if a person smells a certain way? 8- How about smoking?
*** Questions About Me ***
Does the thought excite you? Care to share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
How many times do you think you have “made love”?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
89~ Do you like taking showers together?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
If you say it, I will stop, and we can talk about it when you are ready.
If you win, what will you make them do?
34~ Do you like the lights on or off during sex?
18- How often do you drink alcohol? What is your favorite drink?
Repairman/Lonely Wife Virgin/Experienced
11- What's your favorite restaurant? What’s your least favorite?
Do you have a favorite? Is it ok if your partner does?
4- For a pet, Cat, dog or other?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.