What is the most interesting question you can ask to get to know someone?
11.06.2025 05:47
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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)
15~ Have you ever been “in love”? Who? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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…
19- What’s your favorite fairytale? What’s your least favorite?
I always feel very tired after I do some exercises, even after a night's sleep. What's the problem?
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?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What would you say to prove to yourself that it was really you?
Would /have you ever given your partner a lap dance and Striptease?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
What’s a sleep paralysis demon? And other facts of the bizarre phenomenon - CNN
42~ What’s your biggest regret in life?
53~ How much can you tell me about the one thing you are most passionate about?
15- What's your favorite saying? What word or phrase is your least favorite?
Can you tell me a depressing story?
11- How about if they like a certain sports team? 12-How about drinking too much?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
10- List 5 of your top pet peeves.
Terraforming Mars Isn’t Sci-Fi Anymore – Here’s What It Would Take - SciTechDaily
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?
What have you learned about me that was new and/or surprising?
7- What are your thoughts on religion? Is there an afterlife?
21- What's your favorite way to spend a weekend or time off?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Why is it that women are stronger than men nowadays?
Would you do it again, and would you rather 2 females or 2 males?
*** Random Questions ***
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
How old are you? Male or Female?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Will Canadians still buy American products?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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…
Hubble reveals 20-year time-lapse of Uranus' changing atmosphere - TechSpot
71~ Would you give your partner a hand or foot job? Would you receive one?
What was the longest? What was the shortest?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Do older women know what they want?
13- What is the craziest/scariest thing you've ever done?
51~ What tends to bring a smile to your face?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Louisville earns College World Series trip with 3-2 win over Miami - Card Chronicle
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Ryan Blaney hits right notes in Nashville, lands first Cup Series win of season - NASCAR.com
37- Do you like your name? If you could change it, what would you change it too?
Do you like it when they show and tell you what they want?
Have you ever? Care to Share?
Your TRICARE Checklist for Moving - TRICARE Newsroom (.mil)
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Nurse/Patient Celebrity/Fan
Get this wrong and this could mean the end… :-) some funny, some not…
70~ Would/do you have/like anal sex?
83~ How do you feel about Porn?
12- What is the weirdest thing you've ever eaten?
4- For a pet, Cat, dog or other?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
81~ Do you have any kinks and/or fetishes?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
14- What's your favorite dessert? 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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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,
7-What do I do in bed that drives you wild? How about, what turns you off?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Master/Slave Boss/Maid
30~ What's something unexpected that turns you on?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
If you win, what will you make them do?
If you say it, I will stop, and we can talk about it when you are ready.
Would you ever want to be woken up with oral and/or intercourse?
(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…)
33- Beach or Mountains? Or is there another place to like better?
27- What was/ is nickname? Does it have a meaning behind it?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
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?
8- What are your thoughts on politics?
If NO, would you ever have one? Would it be with 2 men or 2 women?
38~ Share your most embarrassing sexual memory?
What do you dislike about me? I asked you to be 100% honest.
10~ How many dates are necessary before you to have sex with someone?
76~ Have you had a threesome? Care to Share?
3- What Superhero or Superpower would you want to be/have?
58~ Have you ever taken Nude or Hard-core photos and/or videos? 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?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
22- What is your favorite childhood memory? What is your least favorite?
18- How often do you drink alcohol? What is your favorite drink?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
13~ Is there a difference between, making love, having sex, and fucking?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
How about if they talk dirty and/or call you names?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
11~ Have you ever been caught by your parents or children or others while having sex?
31- If given a chance to be immortal, would you take it? Why?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
67~ Do you like it when your partner moans and/or is vocal during sex?
How many partners have you had oral sex with? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
21~ What was the best date you ever went on? What has been the worst?
51~ Are you willing to play adult games with your partner?
29~ What are some things that turn you off? What is your biggest turn off?
52~ What are your hobbies?
What have you learned about yourself that you did not before this?
Do you think this brought you closer together?
22- Do you have any birth marks? How about scars? Care to share how you got them?
1- What was your first impression of me? Has it changed?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
18~ Who/when was your first “crush”?
36~ What is your favorite time of day to have sex/make love?
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
19~ Who/when was your first “heartbreak”?
20- What’s your favorite candy? What’s your least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Family Relation Age Play
*** What’s Your Favorite…? ***
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
17- Have you ever done drugs? Which ones? How often?
Model/Photographer Police/Criminal
Do you have a favorite? Is it ok if your partner does?
Any that are a turn off?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
3- What’s your favorite smell? Do you a least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Doctor/Nurse Stripper/Client
17- What’s your favorite holiday? What’s your least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
65~ Describe the best orgasm you’ve ever had? Care to share?
What is your view on sex? Meaning, When/Where/ How often/
Prisoner/Prison Guard Landlord/Tenant
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
33- If you could visit any time period, when would you pick? Please explain why?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
28~ What are some things that turn on? What is your biggest turn on?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
34- Ever been to a concert? What was your favorite? Who would you like to see?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Do you like the “69” position? Do you prefer to be on top or bottom?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Teacher/Student Stranger/One Night Stand
*** Deal Breaker Questions ***
47~ What would be your dream job and why?
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?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
61~ How willing would you be to try new sexual positions?
* Give a rating for each one (0-100)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
5~ When you first started having sex, was it what you thought it would be?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
13- What’s your favorite drink? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
48~ Have you ever paid or been paid for sex?
19- Do/have you smoked? What do you prefer? How often?
Any that are a turn off?
44~ Care to share something about yourself that no one else knows about you?
5- Have you ever been hypnotized? Would you allow yourself to be?
Escort/Client Job Applicant/Hiring Manager
Please share Did you stop?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
If yes, what?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
9- If you could have three wishes, what would they be? Why?
92~ Everyone needs a “safe” word. What is yours?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you mind if your partner watched it? How about together vs alone?
15- What bad habit do you wish you could quit? Do you have any addictions?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
2- What’s your favorite color? Do you a least favorite?
34~ Do you like the lights on or off during sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
62~ Have you used adult toys?
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?
Over time has your thoughts on sex changed?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Will you cheat again? How can, you be sure? Define what cheating is to you.
The Ice Breaker Questions
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
23- What is your dream job? What was it as a child?
29- How superstitious are you?
How many times do you think you have “made love”?
13- How about having a certain hair cut/style?
Nothing too Serious
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
You know that I will be 100% truthful, so ask.
Do you watch it? What is your favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
25~ How do you feel about PDA? (Public Display of Affection)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Repairman/Lonely Wife Virgin/Experienced
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
84~ How do you feel about reading/listening to adult stories?
How well do you know me? And some of your thoughts about me
Does the thought excite you? Care to share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
*** Questions about Relationships/Past ***
28- What are some things that people do that irritate you?
7- What if a person smells a certain way? 8- How about smoking?
I would allow you to do it… What would you do to me?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Would you read them together?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
36- Do you play video games? What is your favorite? Do you a least favorite?
92~ Have you ever had or have an STD? How many? What was it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
*** Questions About Me ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
32- What's your greatest talent? Can I see it right now?
52~ Are you willing to make “those types” of bets with your partner?
9- Is there something you’ve always wanted to ask me but you’re afraid?
89~ Do you like taking showers together?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
11- List at least 5 things on your bucket list. Have you done any of them already?
39~ What are your love languages?
1~ How old were you when you had your first kiss? Who? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
12- What’s your favorite food? What’s your least favorite?
What is your favorite position? Why?
10- What is your favorite family tradition? What’s your least favorite?
49~ How many times have you been married? Why did they end?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
9- What’s your favorite season and why? What’s your least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
1- What’s your favorite animal? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
50~ How many children do you have? What are their ages?
26~ What side of the bed do you sleep on?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
48~ Do you have any siblings? Are you close to your family?