What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 00:52
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
27- What was/ is nickname? Does it have a meaning behind it?
Could supermassive black holes anchor the tiniest galaxies? - Big Think
Would you ever want to be woken up with oral and/or intercourse?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
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?
Hillary thinks we must censor or "we lose total control". Why does she demand total control?
How many times do you think you have “made love”?
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…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Who are the archers in Genesis 49:23?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Model/Photographer Police/Criminal
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
What is the sum of X+XX+XXX+XXXX?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
7- What if a person smells a certain way? 8- How about smoking?
*** Random Questions ***
Why do older men like to get anal sex?
48~ Do you have any siblings? Are you close to your family?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Will you kiss after your partner has gone down on you? Swallow or spit semen?
3- Should Pluto still be considered a planet? 4- How about smoking?
29~ What are some things that turn you off? What is your biggest turn off?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
The Ice Breaker Questions
Would /have you ever given your partner a lap dance and Striptease?
14- What's your favorite dessert? Do you a least favorite?
What have you learned about yourself that you did not before this?
51~ What tends to bring a smile to your face?
25~ How do you feel about PDA? (Public Display of Affection)
5~ When you first started having sex, was it what you thought it would be?
30~ What's something unexpected that turns you on?
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?
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?
Would you read them together?
Why can’t my wife just accept the fact that I’m going to cheat?
19- What’s your favorite fairytale? What’s your least favorite?
89~ Do you like taking showers together?
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?
Can I see some saggy tit pics and huge areolas pics?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
7-What do I do in bed that drives you wild? How about, what turns you off?
19- Do/have you smoked? What do you prefer? How often?
What is the difference between heaven and heavens?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
*** Questions about Relationships/Past ***
Which city should one visit between Nice and Cannes? Why?
What would you say to prove to yourself that it was really you?
18- How often do you drink alcohol? What is your favorite drink?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
28- What are some things that people do that irritate you?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
1- What was your first impression of me? Has it changed?
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,
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
39~ What are your love languages?
*** Questions About Me ***
13- How about having a certain hair cut/style?
13~ Is there a difference between, making love, having sex, and fucking?
5- Have you ever been hypnotized? Would you allow yourself to be?
12- What’s your favorite food? What’s your least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
31- If given a chance to be immortal, would you take it? Why?
Over time has your thoughts on sex changed?
33- Beach or Mountains? Or is there another place to like better?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Do you have a favorite? Is it ok if your partner does?
Do you think this brought you closer together?
62~ Have you used adult toys?
29- How superstitious are you?
17- What’s your favorite holiday? What’s your least favorite?
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…
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
84~ How do you feel about reading/listening to adult stories?
Doctor/Nurse Stripper/Client
Prisoner/Prison Guard Landlord/Tenant
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
How well do you know me? And some of your thoughts about me
9- What’s your favorite season and why? What’s your least favorite?
Family Relation Age Play
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
Master/Slave Boss/Maid
36- Do you play video games? What is your favorite? Do you a least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Would you allow me to clean every part of your body with my soapy hands and fingers?
21- What's your favorite way to spend a weekend or time off?
Nothing too Serious
What’s the longest time you gone without having sex, after, having it? How much time between the others?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
If YES, was it with 2 men or 2 women? Did you enjoy it?
51~ Are you willing to play adult games with your partner?
65~ Describe the best orgasm you’ve ever had? Care to share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
What is your view on sex? Meaning, When/Where/ How often/
36~ What is your favorite time of day to have sex/make love?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
19~ Who/when was your first “heartbreak”?
11- List at least 5 things on your bucket list. Have you done any of them already?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
38~ Share your most embarrassing sexual memory?
47~ What would be your dream job and why?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
3- What Superhero or Superpower would you want to be/have?
82~ Do you have any fantasies involving Role-Playing?
How many partners have you had oral sex with? Who? Care to Share?
Escort/Client Job Applicant/Hiring Manager
6- Do you have dreams? Can you remember them? What do you usually dream about?
Does the thought excite you? Care to share?
44~ Care to share something about yourself that no one else knows about you?
Have you ever? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Do you like it when they show and tell you what they want?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
13- What is the craziest/scariest thing you've ever done?
37- Do you like your name? If you could change it, what would you change it too?
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?
81~ Do you have any kinks and/or fetishes?
9- Is there something you’ve always wanted to ask me but you’re afraid?
28~ What are some things that turn on? What is your biggest turn on?
67~ Do you like it when your partner moans and/or is vocal during sex?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
50~ How many children do you have? What are their ages?
Would you do it again, and would you rather 2 females or 2 males?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
(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…)
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What was the longest? What was the shortest?
22- What is your favorite childhood memory? What is your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
34- Ever been to a concert? What was your favorite? Who would you like to see?
10~ How many dates are necessary before you to have sex with someone?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
15~ Have you ever been “in love”? Who? 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?
2- What’s your favorite color? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
8- What are your thoughts on politics?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
17- Have you ever done drugs? Which ones? How often?
20- What’s your favorite candy? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
1- What’s your favorite animal? Do you a least favorite?
*** What’s Your Favorite…? ***
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?
Any that are a turn off?
11- How about if they like a certain sports team? 12-How about drinking too much?
61~ How willing would you be to try new sexual positions?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What have you learned about me that was new and/or surprising?
11- What's your favorite restaurant? What’s your least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
3- What’s your favorite smell? Do you a least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
You know that I will be 100% truthful, so ask.
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Please share Did you stop?
42~ What’s your biggest regret in life?
10- List 5 of your top pet peeves.
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
15- What bad habit do you wish you could quit? Do you have any addictions?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
7- What are your thoughts on religion? Is there an afterlife?
83~ How do you feel about Porn?
Get this wrong and this could mean the end… :-) some funny, some not…
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
13- What’s your favorite drink? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
21~ What was the best date you ever went on? What has been the worst?
8- What's your favorite flavor of ice cream? Do you a least favorite?
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Can you Deep Throat? Do you like the taste of yourself?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Do you watch it? What is your favorite?
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?
71~ Would you give your partner a hand or foot job? Would you receive one?
92~ Everyone needs a “safe” word. What is yours?
92~ Have you ever had or have an STD? How many? What was it?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
9~ How many times over your lifetime do you think you have had sex so far?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
How old are you? Male or Female?
Teacher/Student Stranger/One Night Stand
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
1~ How old were you when you had your first kiss? Who? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
* Give a rating for each one (0-100)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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)
32- What's your greatest talent? Can I see it right now?
What is your favorite toy? Ever wanted to try a specific toy?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
9- If you could have three wishes, what would they be? Why?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How about if they talk dirty and/or call you names?
18~ Who/when was your first “crush”?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Would you mind if your partner watched it? How about together vs alone?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
52~ What are your hobbies?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
70~ Would/do you have/like anal sex?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
I would allow you to do it… What would you do to me?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
What is your favorite position? Why?
If you win, what will you make them do?
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
12- What is the weirdest thing you've ever eaten?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
*** Deal Breaker Questions ***
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Any that are a turn off?
Nurse/Patient Celebrity/Fan
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?
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?
48~ Have you ever paid or been paid for sex?
Will you cheat again? How can, you be sure? Define what cheating is to you.
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
26~ What side of the bed do you sleep on?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
34~ Do you like the lights on or off during sex?
What do you dislike about me? I asked you to be 100% honest.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
53~ How much can you tell me about the one thing you are most passionate about?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
If yes, what?
49~ How many times have you been married? Why did they end?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?