What is the most interesting question you can ask to get to know someone?
10.06.2025 01:24
41~ Are there moments in your past that you would want to change? Please share 3 of them.
* Give a rating for each one (0-100)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Would you mind if your partner watched it? How about together vs alone?
42~ What’s your biggest regret in life?
9- What’s your favorite season and why? What’s your least favorite?
Has anyone ever participated in a gang bang and what was it like?
1- What was your first impression of me? Has it changed?
*** Deal Breaker Questions ***
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Can you write a poem or short story based on the first image that shows up on Pinterest?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Have husbands and wives ever had a threesome with someone in real life? How did it happen?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
*** Questions about Relationships/Past ***
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What was the worst spanking you ever got? Why did you get it, and how was it given to you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
1- What’s your favorite animal? Do you a least favorite?
22- What is your favorite childhood memory? What is your least favorite?
If there was only one man remaining on the Earth, would this be regarded as extinction?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
9~ How many times over your lifetime do you think you have had sex so far?
Jimmy Buffett's Wife Files to Remove Co-Trustee on $275 Million Estate - Variety
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
70~ Would/do you have/like anal sex?
No. 2 Coco Gauff faces No. 1 Aryna Sabalenka in French Open women’s final - NBC Sports
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
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 you lose, are you willing to be their sex slave for a day, (anything goes)?
What does "feeling like your life is over" mean and why is it not in any dictionary online?
45~ How do you feel about me blindfolding you? How about blindfolding me?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
7- What if a person smells a certain way? 8- How about smoking?
What are some tips for balancing chores, work, and family life as an adult with children?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
83~ How do you feel about Porn?
48~ Do you have any siblings? Are you close to your family?
What is the best way to keep my vagina clean and fresh?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
33- Beach or Mountains? Or is there another place to like better?
62~ Have you used adult toys?
How short is too short for a skirt?
What is your favorite position? Why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Any that are a turn off?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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?
28~ What are some things that turn on? What is your biggest turn on?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
39~ What are your love languages?
11- What's your favorite restaurant? What’s your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
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…
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How many times do you think you have “made love”?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
36~ What is your favorite time of day to have sex/make love?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
11- List at least 5 things on your bucket list. Have you done any of them already?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
I would allow you to do it… What would you do to me?
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)
If you win, what will you make them do?
34~ Do you like the lights on or off during sex?
Doctor/Nurse Stripper/Client
19- Do/have you smoked? What do you prefer? How often?
19~ Who/when was your first “heartbreak”?
25~ How do you feel about PDA? (Public Display of Affection)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
10~ How many dates are necessary before you to have sex with someone?
34- Ever been to a concert? What was your favorite? Who would you like to see?
The Ice Breaker Questions
89~ Do you like taking showers together?
23- What is your dream job? What was it as a child?
82~ Do you have any fantasies involving Role-Playing?
What have you learned about me that was new and/or surprising?
92~ Have you ever had or have an STD? How many? What was it?
Would you allow me to clean every part of your body with my soapy hands and fingers?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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?
Can you Deep Throat? Do you like the taste of yourself?
29~ What are some things that turn you off? What is your biggest turn off?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Do you watch it? What is your favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
30~ What's something unexpected that turns you on?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
18~ Who/when was your first “crush”?
Would you read them together?
How many partners have you had oral sex with? Who? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
9- If you could have three wishes, what would they be? Why?
15~ Have you ever been “in love”? Who? Care to Share?
Master/Slave Boss/Maid
29- How superstitious are you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Do you like it when they show and tell you what they want?
Nothing too Serious
Would you ever want to be woken up with oral and/or intercourse?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
If yes, what?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
38~ Share your most embarrassing sexual memory?
Teacher/Student Stranger/One Night Stand
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Would you do it again, and would you rather 2 females or 2 males?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
47~ What would be your dream job and why?
(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…)
Repairman/Lonely Wife Virgin/Experienced
Will you cheat again? How can, you be sure? Define what cheating is to you.
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
53~ How much can you tell me about the one thing you are most passionate about?
What is your favorite toy? Ever wanted to try a specific toy?
Over time has your thoughts on sex changed?
32- What's your greatest talent? Can I see it right now?
9- Is there something you’ve always wanted to ask me but you’re afraid?
44~ Care to share something about yourself that no one else knows about you?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
92~ Everyone needs a “safe” word. What is yours?
Do you like the “69” position? Do you prefer to be on top or bottom?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
3- Should Pluto still be considered a planet? 4- How about smoking?
28- What are some things that people do that irritate you?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
*** What’s Your Favorite…? ***
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
26~ What side of the bed do you sleep on?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
10- List 5 of your top pet peeves.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
2- What’s your favorite color? Do you a least favorite?
3- What’s your favorite smell? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
40~ What’s the weirdest place you’ve ever had sex?
How old are you? Male or Female?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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,
1~ How old were you when you had your first kiss? Who? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
How about if they talk dirty and/or call you names?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
48~ Have you ever paid or been paid for sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
14- What's your favorite dessert? Do you a least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
17- What’s your favorite holiday? What’s your least favorite?
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?
19- What’s your favorite fairytale? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
8- What are your thoughts on politics?
52~ What are your hobbies?
20- What’s your favorite candy? What’s your least favorite?
51~ Are you willing to play adult games with your partner?
*** Questions About Me ***
What would you say to prove to yourself that it was really you?
Get this wrong and this could mean the end… :-) some funny, some not…
Do you have a favorite? Is it ok if your partner does?
81~ Do you have any kinks and/or fetishes?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
35- Do you like playing board or cards game? 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?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Would /have you ever given your partner a lap dance and Striptease?
50~ How many children do you have? What are their ages?
52~ Are you willing to make “those types” of bets with your partner?
7- What are your thoughts on religion? Is there an afterlife?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
14- What is an embarrassing moment in your life? How about your most embarrassing?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Please share Did you stop?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
8- What's your favorite flavor of ice cream? Do you a least favorite?
How well do you know me? And some of your thoughts about me
Will you kiss after your partner has gone down on you? Swallow or spit semen?
You know that I will be 100% truthful, so ask.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Does the thought excite you? Care to share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
67~ Do you like it when your partner moans and/or is vocal during sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
13- What’s your favorite drink? What’s your least favorite?
13- How about having a certain hair cut/style?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
51~ What tends to bring a smile to your face?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
15- What bad habit do you wish you could quit? Do you have any addictions?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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?
10- What is your favorite family tradition? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
76~ Have you had a threesome? Care to Share?
61~ How willing would you be to try new sexual positions?
If you say it, I will stop, and we can talk about it when you are ready.
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
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?
18- How often do you drink alcohol? What is your favorite drink?
13~ Is there a difference between, making love, having sex, and fucking?
11- How about if they like a certain sports team? 12-How about drinking too much?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
21- What's your favorite way to spend a weekend or time off?
84~ How do you feel about reading/listening to adult stories?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral 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?
Nurse/Patient Celebrity/Fan
Escort/Client Job Applicant/Hiring Manager
What have you learned about yourself that you did not before this?
What was the longest? What was the shortest?
36- Do you play video games? What is your favorite? Do you a least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
*** Random Questions ***
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
12- What’s your favorite food? What’s your least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
13- What is the craziest/scariest thing you've ever done?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
65~ Describe the best orgasm you’ve ever had? Care to share?
12- What is the weirdest thing you've ever eaten?
27- What was/ is nickname? Does it have a meaning behind it?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
3- What Superhero or Superpower would you want to be/have?
Do you think this brought you closer together?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
49~ How many times have you been married? Why did they end?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
4- For a pet, Cat, dog or other?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Family Relation Age Play
33- If you could visit any time period, when would you pick? Please explain why?
7-What do I do in bed that drives you wild? How about, what turns you off?
31- If given a chance to be immortal, would you take it? Why?
Prisoner/Prison Guard Landlord/Tenant
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What do you dislike about me? I asked you to be 100% honest.
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…
21~ What was the best date you ever went on? What has been the worst?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
6- Do you have dreams? Can you remember them? What do you usually dream about?
5- Have you ever been hypnotized? Would you allow yourself to be?
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?
17- Have you ever done drugs? Which ones? How often?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Model/Photographer Police/Criminal
Have you ever? Care to Share?
Any that are a turn off?