What is the most interesting question you can ask to get to know someone?
12.06.2025 00:48
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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?
I would allow you to do it… What would you do to me?
What are you struggling with in your life? What would you like to have instead?
10- List 5 of your top pet peeves.
18- What’s your favorite way to relax after a long day? What’s your least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Do older men realize that younger women usually do not prefer them?
5- Have you ever been hypnotized? Would you allow yourself to be?
Get this wrong and this could mean the end… :-) some funny, some not…
28~ What are some things that turn on? What is your biggest turn on?
Is it legal for an employer to ask why you are taking time off from work?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
27- What was/ is nickname? Does it have a meaning behind it?
Please share Did you stop?
Scientists learn how mosquitoes outsmart and evade human defenses - Earth.com
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
5~ When you first started having sex, was it what you thought it would be?
Can you Deep Throat? Do you like the taste of yourself?
71~ Would you give your partner a hand or foot job? Would you receive one?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Suspect in Boulder Molotov attack faces federal hate crime charge - Axios
62~ Have you used adult toys?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Will you cheat again? How can, you be sure? Define what cheating is to you.
I gave Google’s AI Mode a shot, but I’m still sticking with Perplexity - Android Authority
92~ Have you ever had or have an STD? How many? What was it?
89~ Do you like taking showers together?
* Give a rating for each one (0-100)
Meta in Talks for Scale AI Investment That Could Top $10 Billion - Bloomberg
67~ Do you like it when your partner moans and/or is vocal during sex?
*** Deal Breaker Questions ***
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
What is your first experience having sex with older men?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
How many times do you think you have “made love”?
36~ What is your favorite time of day to have sex/make love?
Trumpworld Is Fighting Over ‘Official’ Crypto Wallet - WIRED
Nothing too Serious
31- If given a chance to be immortal, would you take it? Why?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
49~ How many times have you been married? Why did they end?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
1- What’s your favorite animal? Do you a least favorite?
92~ Everyone needs a “safe” word. What is yours?
Would you allow me to clean every part of your body with my soapy hands and fingers?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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 is your favorite toy? Ever wanted to try a specific toy?
18~ Who/when was your first “crush”?
11~ Have you ever been caught by your parents or children or others while having sex?
What do you dislike about me? I asked you to be 100% honest.
52~ What are your hobbies?
19- What’s your favorite fairytale? What’s your least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
76~ Have you had a threesome? Care to Share?
2- What’s your favorite color? Do you a least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
14- What's your favorite dessert? Do you a least favorite?
4- For a pet, Cat, dog or other?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
10~ How many dates are necessary before you to have sex with someone?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
40~ What’s the weirdest place you’ve ever had sex?
38~ Share your most embarrassing sexual memory?
Family Relation Age Play
Would you mind if your partner watched it? How about together vs alone?
If yes, what?
*** Random Questions ***
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Master/Slave Boss/Maid
61~ How willing would you be to try new sexual positions?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
84~ How do you feel about reading/listening to adult stories?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
9- If you could have three wishes, what would they be? Why?
13~ Is there a difference between, making love, having sex, and fucking?
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?
9- Is there something you’ve always wanted to ask me but you’re afraid?
7- What if a person smells a certain way? 8- How about smoking?
Doctor/Nurse Stripper/Client
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
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?
29~ What are some things that turn you off? What is your biggest turn off?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
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?
What would you say to prove to yourself that it was really you?
17- Have you ever done drugs? Which ones? How often?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
12- What’s your favorite food? What’s your least favorite?
What have you learned about yourself that you did not before this?
19~ Who/when was your first “heartbreak”?
Repairman/Lonely Wife Virgin/Experienced
What was the longest? What was the shortest?
39~ What are your love languages?
53~ How much can you tell me about the one thing you are most passionate about?
Model/Photographer Police/Criminal
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
3- What’s your favorite smell? Do you a least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Do you like the “69” position? Do you prefer to be on top or bottom?
48~ Have you ever paid or been paid for sex?
37- Do you like your name? If you could change it, what would you change it too?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Any that are a turn off?
Nurse/Patient Celebrity/Fan
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Would you read them together?
Does the thought excite you? Care to share?
The Ice Breaker Questions
(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…)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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?
70~ Would/do you have/like anal sex?
9~ How many times over your lifetime do you think you have had sex so far?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
What is your favorite position? Why?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
10- What is your favorite family tradition? What’s your least favorite?
12- What is the weirdest thing you've ever eaten?
Do you watch it? What is your favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
28- What are some things that people do that irritate you?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Any that are a turn off?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
33- If you could visit any time period, when would you pick? Please explain why?
Escort/Client Job Applicant/Hiring Manager
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
9- What’s your favorite season and why? 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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
13- What is the craziest/scariest thing you've ever done?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
8- What are your thoughts on politics?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
7-What do I do in bed that drives you wild? How about, what turns you off?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
36- Do you play video games? What is your favorite? Do you a 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…
24~ What are your expectations in a relationship? (I know a very big question, take your time)
18- How often do you drink alcohol? What is your favorite drink?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
13- How about having a certain hair cut/style?
25~ How do you feel about PDA? (Public Display of Affection)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Would you do it again, and would you rather 2 females or 2 males?
How many partners have you had oral sex with? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
48~ Do you have any siblings? Are you close to your family?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
29- How superstitious are you?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
That one or two things that made you go hmmmm, OMG or wow!
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
51~ What tends to bring a smile to your face?
6- Do you have dreams? Can you remember them? What do you usually dream about?
13- What’s your favorite drink? What’s your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
19- Do/have you smoked? What do you prefer? How often?
33- Beach or Mountains? Or is there another place to like better?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
82~ Do you have any fantasies involving Role-Playing?
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…
What’s the longest time you gone without having sex, after, having it? How much time between the others?
17- What’s your favorite holiday? What’s your least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
Do you like it when they show and tell you what they want?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
47~ What would be your dream job and why?
22- What is your favorite childhood memory? What is your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
*** Questions about Relationships/Past ***
8- What's your favorite flavor of ice cream? Do you a least favorite?
Would you ever want to be woken up with oral and/or intercourse?
30~ What's something unexpected that turns you on?
How about if they talk dirty and/or call you names?
Teacher/Student Stranger/One Night Stand
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What is your view on sex? Meaning, When/Where/ How often/
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
83~ How do you feel about Porn?
21- What's your favorite way to spend a weekend or time off?
32- What's your greatest talent? Can I see it right now?
Prisoner/Prison Guard Landlord/Tenant
You know that I will be 100% truthful, so ask.
51~ Are you willing to play adult games with your partner?
If YES, was it with 2 men or 2 women? Did you enjoy it?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
42~ What’s your biggest regret in life?
How well do you know me? And some of your thoughts about me
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
23- What is your dream job? What was it as a child?
*** What’s Your Favorite…? ***
*** Questions About Me ***
15- What bad habit do you wish you could quit? Do you have any addictions?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
7- What are your thoughts on religion? Is there an afterlife?
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?
Do you have a favorite? Is it ok if your partner does?
Would /have you ever given your partner a lap dance and Striptease?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
45~ How do you feel about me blindfolding you? How about blindfolding me?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
What have you learned about me that was new and/or surprising?
How old are you? Male or Female?
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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?
50~ How many children do you have? What are their ages?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
11- How about if they like a certain sports team? 12-How about drinking too much?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
34~ Do you like the lights on or off during sex?
Do you think this brought you closer together?
34- Ever been to a concert? What was your favorite? Who would you like to see?
11- List at least 5 things on your bucket list. Have you done any of them already?
1- What was your first impression of me? Has it changed?
65~ Describe the best orgasm you’ve ever had? Care to share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
3- What Superhero or Superpower would you want to be/have?
44~ Care to share something about yourself that no one else knows about you?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Over time has your thoughts on sex changed?
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)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
If you win, what will you make them do?
21~ What was the best date you ever went on? What has been the worst?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
80~ Share your top three fantasies/desires. (Be detailed) 😊
20- What’s your favorite candy? What’s your 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…
If you say it, I will stop, and we can talk about it when you are ready.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
81~ Do you have any kinks and/or fetishes?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
52~ Are you willing to make “those types” of bets with your partner?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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,
11- What's your favorite restaurant? What’s your least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
3- Should Pluto still be considered a planet? 4- How about smoking?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Have you ever? Care to Share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
15~ Have you ever been “in love”? Who? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?