What is the most interesting question you can ask to get to know someone?
14.06.2025 13:20
9~ How many times over your lifetime do you think you have had sex so far?
25~ How do you feel about PDA? (Public Display of Affection)
What is your favorite toy? Ever wanted to try a specific toy?
Do married men know when their wives are having affairs?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
36~ What is your favorite time of day to have sex/make love?
How old are you? Male or Female?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Do you think this brought you closer together?
What are the psychological reasons behind an extreme obsession with another human being?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
11~ Have you ever been caught by your parents or children or others while having sex?
32- What's your greatest talent? Can I see it right now?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Can you name a female actress who has had bad timing or luck in her film career?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
That one or two things that made you go hmmmm, OMG or wow!
Why do I sweat so much at the gym?
9- Is there something you’ve always wanted to ask me but you’re afraid?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
3- What Superhero or Superpower would you want to be/have?
Do leftists understand why young men are becoming more right-wing?
8- What's your favorite flavor of ice cream? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
I would allow you to do it… What would you do to me?
Why do men like to have sex with a woman's ass?
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)
27- What was/ is nickname? Does it have a meaning behind it?
7- What are your thoughts on religion? Is there an afterlife?
South Florida-based Silver Airways shuts down, stranding travelers - Sun Sentinel
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
If YES, was it with 2 men or 2 women? Did you enjoy it?
The Ice Breaker Questions
Where's the Civil War everyone on the left said would happen?
What is your view on sex? Meaning, When/Where/ How often/
1~ How old were you when you had your first kiss? Who? Care to Share?
Nothing too Serious
Why is there so much evil in the world?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
(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…)
18- How often do you drink alcohol? What is your favorite drink?
89~ Do you like taking showers together?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
29~ What are some things that turn you off? What is your biggest turn off?
13~ Is there a difference between, making love, having sex, and fucking?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you watch it? What is your favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
62~ Have you used adult toys?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
13- How about having a certain hair cut/style?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
*** What’s Your Favorite…? ***
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?
82~ Do you have any fantasies involving Role-Playing?
76~ Have you had a threesome? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
1- What was your first impression of me? Has it changed?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
13- What’s your favorite drink? What’s your least favorite?
4- For a pet, Cat, dog or other?
60~ How important is oral sex? Do you like receiving? Do you like giving?
3- Should Pluto still be considered a planet? 4- How about smoking?
14- What is an embarrassing moment in your life? How about your most embarrassing?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
39~ What are your love languages?
Any that are a turn off?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
If you say it, I will stop, and we can talk about it when you are ready.
Prisoner/Prison Guard Landlord/Tenant
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
48~ Have you ever paid or been paid for sex?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
8- What are your thoughts on politics?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
How well do you know me? And some of your thoughts about me
50~ How many children do you have? What are their ages?
Nurse/Patient Celebrity/Fan
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Do you like the “69” position? Do you prefer to be on top or bottom?
7- What if a person smells a certain way? 8- How about smoking?
Master/Slave Boss/Maid
26~ What side of the bed do you sleep on?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
30~ What's something unexpected that turns you on?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
You know that I will be 100% truthful, so ask.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
18~ Who/when was your first “crush”?
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?
How many times do you think you have “made love”?
Doctor/Nurse Stripper/Client
33- Beach or Mountains? Or is there another place to like better?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
49~ How many times have you been married? Why did they end?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
19- Do/have you smoked? What do you prefer? How often?
83~ How do you feel about Porn?
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…
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
3- What’s your favorite smell? Do you a least favorite?
17- What’s your favorite holiday? What’s your least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
42~ What’s your biggest regret in life?
21~ What was the best date you ever went on? What has been the worst?
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…
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What was the longest? What was the shortest?
61~ How willing would you be to try new sexual positions?
If NO, would you ever have one? Would it be with 2 men or 2 women?
What do you dislike about me? I asked you to be 100% honest.
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Would you allow me to clean every part of your body with my soapy hands and fingers?
5~ When you first started having sex, was it what you thought it would be?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
52~ What are your hobbies?
19- What’s your favorite fairytale? What’s your least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you do it again, and would you rather 2 females or 2 males?
Do you have a favorite? Is it ok if your partner does?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
44~ Care to share something about yourself that no one else knows about you?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Does the thought excite you? Care to share?
1- What’s your favorite animal? Do you a least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you like it when they show and tell you what they want?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
40~ What’s the weirdest place you’ve ever had sex?
Would you mind if your partner watched it? How about together vs alone?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
Can you Deep Throat? Do you like the taste of yourself?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
81~ Do you have any kinks and/or fetishes?
20- What’s your favorite candy? What’s your least favorite?
48~ Do you have any siblings? Are you close to your family?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How many partners have you had oral sex with? Who? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
5- Have you ever been hypnotized? Would you allow yourself to be?
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,
38~ Share your most embarrassing sexual memory?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
*** Questions About Me ***
Repairman/Lonely Wife Virgin/Experienced
71~ Would you give your partner a hand or foot job? Would you receive one?
11- List at least 5 things on your bucket list. Have you done any of them already?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
31- If given a chance to be immortal, would you take it? Why?
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?
11- How about if they like a certain sports team? 12-How about drinking too much?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Model/Photographer Police/Criminal
If yes, what?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
47~ What would be your dream job and why?
37- Do you like your name? If you could change it, what would you change it too?
65~ Describe the best orgasm you’ve ever had? Care to share?
10~ How many dates are necessary before you to have sex with someone?
21- What's your favorite way to spend a weekend or time off?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
9- If you could have three wishes, what would they be? Why?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Over time has your thoughts on sex changed?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
13- What is the craziest/scariest thing you've ever done?
34- Ever been to a concert? What was your favorite? Who would you like to see?
10- List 5 of your top pet peeves.
9- What’s your favorite season and why? What’s your least favorite?
28~ What are some things that turn on? What is your biggest turn on?
53~ How much can you tell me about the one thing you are most passionate about?
70~ Would/do you have/like anal sex?
Escort/Client Job Applicant/Hiring Manager
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What is your favorite position? Why?
45~ How do you feel about me blindfolding you? How about blindfolding me?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
28- What are some things that people do that irritate you?
What have you learned about yourself that you did not before this?
Have you ever? Care to Share?
*** Questions about Relationships/Past ***
14- What's your favorite dessert? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Would you ever want to be woken up with oral and/or intercourse?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
12- What’s your favorite food? What’s your least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
51~ Are you willing to play adult games with your partner?
67~ Do you like it when your partner moans and/or is vocal during sex?
15- What bad habit do you wish you could quit? Do you have any addictions?
Would you read them together?
51~ What tends to bring a smile to your face?
How about if they talk dirty and/or call you names?
34~ Do you like the lights on or off during sex?
Please share Did you stop?
92~ Have you ever had or have an STD? How many? What was it?
If you win, what will you make them do?
2- What’s your favorite color? Do you a least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
What would you say to prove to yourself that it was really you?
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?
Teacher/Student Stranger/One Night Stand
7-What do I do in bed that drives you wild? How about, what turns you off?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Will you cheat again? How can, you be sure? Define what cheating is to you.
19~ Who/when was your first “heartbreak”?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
52~ Are you willing to make “those types” of bets with your partner?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
* Give a rating for each one (0-100)
Get this wrong and this could mean the end… :-) some funny, some not…
Any that are a turn off?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
23- What is your dream job? What was it as a child?
What have you learned about me that was new and/or surprising?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
29- How superstitious are you?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
12- What is the weirdest thing you've ever eaten?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
*** Random Questions ***
36- Do you play video games? What is your favorite? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
6- Do you have dreams? Can you remember them? What do you usually dream about?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
*** Deal Breaker Questions ***
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?
Family Relation Age Play
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
22- Do you have any birth marks? How about scars? Care to share how you got them?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
11- What's your favorite restaurant? What’s your least favorite?
10- What is your favorite family tradition? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?