What is the most interesting question you can ask to get to know someone?
09.06.2025 03:19
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?
9~ How many times over your lifetime do you think you have had sex so far?
1- What’s your favorite animal? Do you a least favorite?
What are some hard rock or heavy metal bands that are overrated?
What is your view on sex? Meaning, When/Where/ How often/
Repairman/Lonely Wife Virgin/Experienced
49~ How many times have you been married? Why did they end?
How do I cope with the fact that I will never have a girlfriend?
52~ Are you willing to make “those types” of bets with your partner?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Any that are a turn off?
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67~ Do you like it when your partner moans and/or is vocal during sex?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
What is unattractive about a nice guy? Why do some women don’t choose nice guys?
38~ Share your most embarrassing sexual memory?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
How many partners have you had oral sex with? Who? Care to Share?
61~ How willing would you be to try new sexual positions?
If yes, what?
28- What are some things that people do that irritate 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…)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
When did you realize that your childhood was not normal?
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?
33- Beach or Mountains? Or is there another place to like better?
34~ Do you like the lights on or off during sex?
Why do men like to have sex with a woman's ass?
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)
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Meta Ray-Ban Glasses are at their Lowest Price Ever: Deal of the Day - NBC News
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
92~ Have you ever had or have an STD? How many? What was it?
39~ What are your love languages?
U.S. economy stalled in May, Fed survey finds - MarketWatch
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Nurse/Patient Celebrity/Fan
1~ How old were you when you had your first kiss? Who? Care to Share?
What does it mean if someone asks if it’s pink?
31- If given a chance to be immortal, would you take it? Why?
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,
36~ What is your favorite time of day to have sex/make love?
In space, no one can hear you scream — But it still gets incredibly noisy - Salon.com
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Nothing too Serious
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- Do/have you smoked? What do you prefer? How often?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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64~ When was your very first orgasm? When was your first from having sex? Care to share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
92~ Everyone needs a “safe” word. What is yours?
Do you think this brought you closer together?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
*** Questions about Relationships/Past ***
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
*** Random Questions ***
47~ What would be your dream job and why?
Get this wrong and this could mean the end… :-) some funny, some not…
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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…
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Over time has your thoughts on sex changed?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
If you say it, I will stop, and we can talk about it when you are ready.
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
81~ Do you have any kinks and/or fetishes?
4- For a pet, Cat, dog or other?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
*** Questions About Me ***
33- If you could visit any time period, when would you pick? Please explain why?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Doctor/Nurse Stripper/Client
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?
48~ Have you ever paid or been paid for sex?
44~ Care to share something about yourself that no one else knows about you?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
89~ Do you like taking showers together?
Do you like the “69” position? Do you prefer to be on top or bottom?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
You know that I will be 100% truthful, so ask.
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
62~ Have you used adult toys?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Teacher/Student Stranger/One Night Stand
3- Should Pluto still be considered a planet? 4- How about smoking?
42~ What’s your biggest regret in life?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
If YES, was it with 2 men or 2 women? Did you enjoy it?
83~ How do you feel about Porn?
19- What’s your favorite fairytale? What’s your least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What would you say to prove to yourself that it was really you?
Would you do it again, and would you rather 2 females or 2 males?
12- What is the weirdest thing you've ever eaten?
How well do you know me? And some of your thoughts about me
23- What is your dream job? What was it as a child?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
7- What are your thoughts on religion? Is there an afterlife?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
36- Do you play video games? What is your favorite? 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…
22- Do you have any birth marks? How about scars? Care to share how you got them?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
11- What's your favorite restaurant? What’s your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Model/Photographer Police/Criminal
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
51~ Are you willing to play adult games with your partner?
1- What was your first impression of me? Has it changed?
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?
51~ What tends to bring a smile to your face?
* Give a rating for each one (0-100)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Would you ever want to be woken up with oral and/or intercourse?
5- Have you ever been hypnotized? Would you allow yourself to be?
12- What’s your favorite food? What’s your least favorite?
Please share Did you stop?
11- How about if they like a certain sports team? 12-How about drinking too much?
10- List 5 of your top pet peeves.
What is your favorite toy? Ever wanted to try a specific toy?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
3- What’s your favorite smell? Do you a least favorite?
If you win, what will you make them do?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
11~ Have you ever been caught by your parents or children or others while having sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
8- What are your thoughts on politics?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
65~ Describe the best orgasm you’ve ever had? 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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
52~ What are your hobbies?
*** What’s Your Favorite…? ***
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Can you Deep Throat? Do you like the taste of yourself?
Would /have you ever given your partner a lap dance and Striptease?
Master/Slave Boss/Maid
The Ice Breaker Questions
18~ Who/when was your first “crush”?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
How about if they talk dirty and/or call you names?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
80~ Share your top three fantasies/desires. (Be detailed) 😊
10- What is your favorite family tradition? What’s your least favorite?
Family Relation Age Play
Do you have a favorite? Is it ok if your partner does?
18- How often do you drink alcohol? What is your favorite drink?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Would you allow me to clean every part of your body with my soapy hands and fingers?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
That one or two things that made you go hmmmm, OMG or wow!
76~ Have you had a threesome? Care to Share?
3- What Superhero or Superpower would you want to be/have?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
14- What is an embarrassing moment in your life? How about your most embarrassing?
Escort/Client Job Applicant/Hiring Manager
Would you read them together?
I would allow you to do it… What would you do to me?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
7-What do I do in bed that drives you wild? How about, what turns you off?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
14- What's your favorite dessert? Do you a least favorite?
84~ How do you feel about reading/listening to adult stories?
21~ What was the best date you ever went on? What has been the worst?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
10~ How many dates are necessary before you to have sex with someone?
11- List at least 5 things on your bucket list. Have you done any of them already?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
20- What’s your favorite candy? What’s your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
13- What is the craziest/scariest thing you've ever done?
How many times do you think you have “made love”?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
32- What's your greatest talent? Can I see it right now?
13~ Is there a difference between, making love, having sex, and fucking?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
29~ What are some things that turn you off? What is your biggest turn off?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
8- What's your favorite flavor of ice cream? Do you a least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
13- How about having a certain hair cut/style?
50~ How many children do you have? What are their ages?
Will you cheat again? How can, you be sure? Define what cheating is to you.
21- What's your favorite way to spend a weekend or time off?
Would you mind if your partner watched it? How about together vs alone?
19~ Who/when was your first “heartbreak”?
26~ What side of the bed do you sleep on?
17- Have you ever done drugs? Which ones? How often?
2- What’s your favorite color? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
What was the longest? What was the shortest?
9- What’s your favorite season and why? What’s your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What is your favorite position? Why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
48~ Do you have any siblings? Are you close to your family?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
29- How superstitious are you?
What have you learned about me that was new and/or surprising?
What have you learned about yourself that you did not before this?
Any that are a turn off?
30~ What's something unexpected that turns you on?
Have you ever? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
17- What’s your favorite holiday? What’s your least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
70~ Would/do you have/like anal sex?
How old are you? Male or Female?
25~ How do you feel about PDA? (Public Display of Affection)
Do you like it when they show and tell you what they want?
34- Ever been to a concert? What was your favorite? Who would you like to see?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
Does the thought excite you? Care to share?
40~ What’s the weirdest place you’ve ever had sex?
Do you watch it? What is your favorite?
5~ When you first started having sex, was it what you thought it would be?
28~ What are some things that turn on? What is your biggest turn on?
7- What if a person smells a certain way? 8- How about smoking?
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?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
9- If you could have three wishes, what would they be? Why?
22- What is your favorite childhood memory? What is your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
*** Deal Breaker Questions ***
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
13- What’s your favorite drink? What’s your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?