What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 06:37
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
36- Do you play video games? What is your favorite? Do you a least favorite?
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?
Why is it common for guys to sleep with 10-20 women then marry a good girl?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Why is the covert narcissist actively avoiding me when they see me everyday?
How old are you? Male or Female?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Why were the Japanese soldiers in WW II so hesitant to surrender in battle?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
If you say it, I will stop, and we can talk about it when you are ready.
Neanderthals Spread Across Asia With Surprising Speed—and Now We Know How - Gizmodo
14- What is an embarrassing moment in your life? How about your most embarrassing?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
10- List 5 of your top pet peeves.
How do you fight the push and pull (manipulation) tactic if you want to win him?
13~ Is there a difference between, making love, having sex, and fucking?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
1- What was your first impression of me? Has it changed?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
From 1 to 10, how dark is the Naruto fandom? Why?
92~ Have you ever had or have an STD? How many? What was it?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
*** Random Questions ***
Do you remember one day, you put a deep smile on someone's face and made them very happy?
47~ What would be your dream job and why?
15- What bad habit do you wish you could quit? Do you have any addictions?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
9- If you could have three wishes, what would they be? Why?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
13- What is the craziest/scariest thing you've ever done?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
51~ What tends to bring a smile to your face?
3- What Superhero or Superpower would you want to be/have?
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,
3- Should Pluto still be considered a planet? 4- How about smoking?
50~ How many children do you have? What are their ages?
Do you have a favorite? Is it ok if your partner does?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
30~ What's something unexpected that turns you on?
13- What’s your favorite drink? What’s your least favorite?
44~ Care to share something about yourself that no one else knows about you?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
26~ What side of the bed do you sleep on?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
21- What's your favorite way to spend a weekend or time off?
You know that I will be 100% truthful, so ask.
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?
Over time has your thoughts on sex changed?
What is your favorite position? Why?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
40~ What’s the weirdest place you’ve ever had sex?
*** What’s Your Favorite…? ***
Family Relation Age Play
Would you mind if your partner watched it? How about together vs alone?
81~ Do you have any kinks and/or fetishes?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
(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…)
19~ Who/when was your first “heartbreak”?
Do you like it when they show and tell you what they want?
14- What's your favorite dessert? Do you a least favorite?
Would you do it again, and would you rather 2 females or 2 males?
What is your favorite toy? Ever wanted to try a specific toy?
60~ How important is oral sex? Do you like receiving? Do you like giving?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
2- What’s your favorite color? Do you a least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
That one or two things that made you go hmmmm, OMG or wow!
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
I would allow you to do it… What would you do to me?
Have you ever? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
12- What is the weirdest thing you've ever eaten?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
48~ Have you ever paid or been paid for sex?
53~ How much can you tell me about the one thing you are most passionate about?
Nothing too Serious
15~ Have you ever been “in love”? Who? Care to Share?
7-What do I do in bed that drives you wild? 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?
37- Do you like your name? If you could change it, what would you change it too?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Do you like the “69” position? Do you prefer to be on top or bottom?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What have you learned about me that was new and/or surprising?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
22- Do you have any birth marks? How about scars? Care to share how you got them?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Nurse/Patient Celebrity/Fan
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?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
4- For a pet, Cat, dog or other?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
If you lose, are you willing to be their sex slave for a day, (anything goes)?
83~ How do you feel about Porn?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
19- Do/have you smoked? What do you prefer? How often?
Please share Did you stop?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
5~ When you first started having sex, was it what you thought it would be?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
7- What if a person smells a certain way? 8- How about smoking?
What do you dislike about me? I asked you to be 100% honest.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
The Ice Breaker Questions
33- If you could visit any time period, when would you pick? Please explain why?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
If yes, what?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Get this wrong and this could mean the end… :-) some funny, some not…
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
19- What’s your favorite fairytale? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
9~ How many times over your lifetime do you think you have had sex so far?
13- How about having a certain hair cut/style?
42~ What’s your biggest regret in life?
8- What's your favorite flavor of ice cream? Do you a 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…
* Give a rating for each one (0-100)
If YES, was it with 2 men or 2 women? Did you enjoy it?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
5- Have you ever been hypnotized? Would you allow yourself to be?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Escort/Client Job Applicant/Hiring Manager
62~ Have you used adult toys?
39~ What are your love languages?
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?
92~ Everyone needs a “safe” word. What is yours?
How many partners have you had oral sex with? Who? Care to Share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
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?
7- What are your thoughts on religion? Is there an afterlife?
11- What's your favorite restaurant? What’s your least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Would you read them together?
52~ What are your hobbies?
17- Have you ever done drugs? Which ones? How often?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
How about if they talk dirty and/or call you names?
Doctor/Nurse Stripper/Client
89~ Do you like taking showers together?
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)
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?
*** Deal Breaker Questions ***
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
45~ How do you feel about me blindfolding you? How about blindfolding me?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
28- What are some things that people do that irritate you?
*** Questions about Relationships/Past ***
10~ How many dates are necessary before you to have sex with someone?
Model/Photographer Police/Criminal
10- What is your favorite family tradition? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
23- What is your dream job? What was it as a child?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
76~ Have you had a threesome? Care to Share?
Master/Slave Boss/Maid
67~ Do you like it when your partner moans and/or is vocal during sex?
28~ What are some things that turn on? What is your biggest turn on?
How well do you know me? And some of your thoughts about me
Any that are a turn off?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
11~ Have you ever been caught by your parents or children or others while having sex?
3- What’s your favorite smell? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
33- Beach or Mountains? Or is there another place to like better?
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?
49~ How many times have you been married? Why did they end?
What would you say to prove to yourself that it was really you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
51~ Are you willing to play adult games with your partner?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
22- What is your favorite childhood memory? What is your least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
8- What are your thoughts on politics?
82~ Do you have any fantasies involving Role-Playing?
What have you learned about yourself that you did not before this?
27- What was/ is nickname? Does it have a meaning behind it?
15- What's your favorite saying? What word or phrase is your least favorite?
21~ What was the best date you ever went on? What has been the worst?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
20- What’s your favorite candy? What’s your least favorite?
Do you think this brought you closer together?
48~ Do you have any siblings? Are you close to your family?
36~ What is your favorite time of day to have sex/make love?
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?
29~ What are some things that turn you off? What is your biggest turn off?
What was the longest? What was the shortest?
65~ Describe the best orgasm you’ve ever had? Care to share?
What is your view on sex? Meaning, When/Where/ How often/
If you win, what will you make them do?
1- What’s your favorite animal? Do you a least favorite?
Does the thought excite you? Care to share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
How many times do you think you have “made love”?
Any that are a turn off?
Do you watch it? What is your favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
34- Ever been to a concert? What was your favorite? Who would you like to see?
61~ How willing would you be to try new sexual positions?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
*** Questions About Me ***
32- What's your greatest talent? Can I see it right now?
18- How often do you drink alcohol? What is your favorite drink?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
70~ Would/do you have/like anal sex?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
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…
Would /have you ever given your partner a lap dance and Striptease?
18~ Who/when was your first “crush”?
31- If given a chance to be immortal, would you take it? Why?
17- What’s your favorite holiday? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
25~ How do you feel about PDA? (Public Display of Affection)
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
1~ How old were you when you had your first kiss? Who? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
9- What’s your favorite season and why? What’s your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
38~ Share your most embarrassing sexual memory?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
34~ Do you like the lights on or off during sex?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Would you ever want to be woken up with oral and/or intercourse?
11- How about if they like a certain sports team? 12-How about drinking too much?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
29- How superstitious are you?
12- What’s your favorite food? What’s your least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?