What is the most interesting question you can ask to get to know someone?
Last Updated: 22.06.2025 01:09
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?
1- What was your first impression of me? Has it changed?
Do you have a favorite? Is it ok if your partner does?
How do I cut off friends that don't contribute to my life?
What have you learned about me that was new and/or surprising?
13~ Is there a difference between, making love, having sex, and fucking?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Experts Just Discovered The Most Effective New Weight Loss Drug—And It's Not Ozempic - AOL.com
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?
8- What are your thoughts on politics?
14- What is an embarrassing moment in your life? How about your most embarrassing?
When you visit a store, do you go to shop or buy?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Can you Deep Throat? Do you like the taste of yourself?
What did your sister do to you that you can never forget?
83~ How do you feel about Porn?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
10- What is your favorite family tradition? What’s your least favorite?
How does the brain decide "what" thought to attach to a feeling?
Any that are a turn off?
15- What bad habit do you wish you could quit? Do you have any addictions?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What are some examples of unofficial acts by presidents?
What would you say to prove to yourself that it was really you?
76~ Have you had a threesome? Care to Share?
You know that I will be 100% truthful, so ask.
Why hasn't Japan legalized same-sex marriage?
13- How about having a certain hair cut/style?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
22- Do you have any birth marks? How about scars? Care to share how you got them?
How often do prisoners try to escape from jail/prison, and how many of them succeed?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
How can I watch porn on TikTok?
Have you ever? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
13- What’s your favorite drink? What’s your least favorite?
51~ Are you willing to play adult games with your partner?
65~ Describe the best orgasm you’ve ever had? Care to share?
1- What’s your favorite animal? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What is your view on sex? Meaning, When/Where/ How often/
Would you read them together?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
53~ How much can you tell me about the one thing you are most passionate about?
*** Questions About Me ***
48~ Have you ever paid or been paid for sex?
Would you ever want to be woken up with oral and/or intercourse?
Would /have you ever given your partner a lap dance and Striptease?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
7- What if a person smells a certain way? 8- How about smoking?
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?
19- What’s your favorite fairytale? What’s your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
If NO, would you ever have one? Would it be with 2 men or 2 women?
5- Have you ever been hypnotized? Would you allow yourself to be?
48~ Do you have any siblings? Are you close to your family?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
84~ How do you feel about reading/listening to adult stories?
28~ What are some things that turn on? What is your biggest turn on?
(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…)
28- What are some things that people do that irritate you?
Any that are a turn off?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you watch it? What is your favorite?
21~ What was the best date you ever went on? What has been the worst?
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”?
18- How often do you drink alcohol? What is your favorite drink?
23- What is your dream job? What was it as a child?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
If yes, what?
Would you mind if your partner watched it? How about together vs alone?
3- What’s your favorite smell? Do you a least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
How about if they talk dirty and/or call you names?
That one or two things that made you go hmmmm, OMG or wow!
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
34- Ever been to a concert? What was your favorite? Who would you like to see?
44~ Care to share something about yourself that no one else knows about you?
Prisoner/Prison Guard Landlord/Tenant
7-What do I do in bed that drives you wild? How about, what turns you off?
17- Have you ever done drugs? Which ones? How often?
36~ What is your favorite time of day to have sex/make love?
50~ How many children do you have? What are their ages?
92~ Have you ever had or have an STD? How many? What was it?
21- What's your favorite way to spend a weekend or time off?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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…
20- What’s your favorite candy? What’s your least favorite?
37- Do you like your name? If you could change it, what would you change it too?
How many times do you think you have “made love”?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
If you win, what will you make them do?
*** Questions about Relationships/Past ***
Do you shave/trim your pubic hair? For you guys do you shave your balls?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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,
Doctor/Nurse Stripper/Client
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Does the thought excite you? Care to share?
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
34~ Do you like the lights on or off during sex?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
Master/Slave Boss/Maid
The Ice Breaker Questions
Do you like the “69” position? Do you prefer to be on top or bottom?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Nurse/Patient Celebrity/Fan
1~ How old were you when you had your first kiss? Who? Care to Share?
*** Deal Breaker Questions ***
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
17- What’s your favorite holiday? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
61~ How willing would you be to try new sexual positions?
11- How about if they like a certain sports team? 12-How about drinking too much?
5~ When you first started having sex, was it what you thought it would be?
11- What's your favorite restaurant? What’s your least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
2- What’s your favorite color? Do you a least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? 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.
Teacher/Student Stranger/One Night Stand
42~ What’s your biggest regret in life?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
10- List 5 of your top pet peeves.
29- How superstitious are you?
Family Relation Age Play
19- Do/have you smoked? What do you prefer? How often?
19~ Who/when was your first “heartbreak”?
36- Do you play video games? What is your favorite? Do you a least favorite?
* Give a rating for each one (0-100)
51~ What tends to bring a smile to your face?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
7- What are your thoughts on religion? Is there an afterlife?
What is your favorite toy? Ever wanted to try a specific toy?
What is your favorite position? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
81~ Do you have any kinks and/or fetishes?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Model/Photographer Police/Criminal
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Over time has your thoughts on sex changed?
How many partners have you had oral sex with? Who? Care to Share?
32- What's your greatest talent? Can I see it right now?
13- What is the craziest/scariest thing you've ever done?
40~ What’s the weirdest place you’ve ever had sex?
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
30~ What's something unexpected that turns you on?
89~ Do you like taking showers together?
52~ What are your hobbies?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Would you do it again, and would you rather 2 females or 2 males?
Get this wrong and this could mean the end… :-) some funny, some not…
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?
9- If you could have three wishes, what would they be? Why?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
12- What’s your favorite food? What’s your least favorite?
*** Random Questions ***
15~ Have you ever been “in love”? Who? Care to Share?
What have you learned about yourself that you did not before this?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
52~ Are you willing to make “those types” of bets with your partner?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
25~ How do you feel about PDA? (Public Display of Affection)
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?
Escort/Client Job Applicant/Hiring Manager
9- What’s your favorite season and why? What’s your least favorite?
70~ Would/do you have/like anal sex?
29~ What are some things that turn you off? What is your biggest turn off?
10~ How many dates are necessary before you to have sex with someone?
12- What is the weirdest thing you've ever eaten?
Do you like it when they show and tell you what they want?
How old are you? Male or Female?
22- What is your favorite childhood memory? What is your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
3- What Superhero or Superpower would you want to be/have?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
*** What’s Your Favorite…? ***
38~ Share your most embarrassing sexual memory?
80~ Share your top three fantasies/desires. (Be detailed) 😊
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
What was the longest? What was the shortest?
11~ Have you ever been caught by your parents or children or others while having sex?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
If you say it, I will stop, and we can talk about it when you are ready.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
49~ How many times have you been married? Why did they end?
27- What was/ is nickname? Does it have a meaning behind it?
7~ How many times in one day have you had sex? Who/When/Where? 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)
4- For a pet, Cat, dog or other?
47~ What would be your dream job and why?
33- Beach or Mountains? Or is there another place to like better?
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?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Please share Did you stop?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
82~ Do you have any fantasies involving Role-Playing?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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…
15- What's your favorite saying? What word or phrase is your least favorite?
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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Nothing too Serious
If you lose, are you willing to be their sex slave for a day, (anything goes)?
26~ What side of the bed do you sleep on?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
9~ How many times over your lifetime do you think you have had sex so far?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Do you think this brought you closer together?
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
How well do you know me? And some of your thoughts about me
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
45~ How do you feel about me blindfolding you? How about blindfolding me?
14- What's your favorite dessert? Do you a least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
11- List at least 5 things on your bucket list. Have you done any of them already?
What do you dislike about me? I asked you to be 100% honest.
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
39~ What are your love languages?
31- If given a chance to be immortal, would you take it? Why?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?