What is the most interesting question you can ask to get to know someone?
07.06.2025 19:31
How many times do you think you have “made love”?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
89~ Do you like taking showers together?
Have you worn a tight black mini skirt?
45~ How do you feel about me blindfolding you? How about blindfolding me?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Nothing too Serious
Scientists uncover key role of thyroid hormones in fear memory formation - PsyPost
3- What Superhero or Superpower would you want to be/have?
3- Should Pluto still be considered a planet? 4- How about smoking?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
20- What’s your favorite candy? What’s your least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
How can I be okay with being ugly? What is the bright side?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
49~ How many times have you been married? Why did they end?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Housing market tide is turning as home prices fall in top cities - Fortune
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Would /have you ever given your partner a lap dance and Striptease?
Owen Wilson Brings Clever, Funny “Stick” in Under Par - Roger Ebert
Would you mind if your partner watched it? How about together vs alone?
51~ What tends to bring a smile to your face?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
19- Do/have you smoked? What do you prefer? How often?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
If you say it, I will stop, and we can talk about it when you are ready.
How did it feel when experiencing gay sex for the first?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
26~ What side of the bed do you sleep on?
39~ What are your love languages?
How can I stop overthinking and take action more quickly?
15~ Have you ever been “in love”? Who? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
31- If given a chance to be immortal, would you take it? Why?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
What World Does Bitcoin Want To Build For Itself? - Defector
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
If you win, what will you make them do?
8- What's your favorite flavor of ice cream? Do you a least favorite?
You know that I will be 100% truthful, so ask.
This Google experimental app lets you run powerful AI models without Wi-Fi - Android Police
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
What have you learned about yourself that you did not before this?
Not into AI? This Windows 11 update improves gaming performance. - Windows Central
1~ How old were you when you had your first kiss? Who? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
36~ What is your favorite time of day to have sex/make love?
What is the Replika app, and how does it work?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Would you ever want to be woken up with oral and/or intercourse?
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…
13- What is the craziest/scariest thing you've ever done?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
19~ Who/when was your first “heartbreak”?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Any that are a turn off?
I would allow you to do it… What would you do to me?
2- What’s your favorite color? Do you a least favorite?
How about if they talk dirty and/or call you names?
52~ What are your hobbies?
5- Have you ever been hypnotized? Would you allow yourself to be?
48~ Do you have any siblings? Are you close to your family?
*** Questions about Relationships/Past ***
3- What was the most surprising thing you’ve learned about me throughout our relationship?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
That one or two things that made you go hmmmm, OMG or wow!
What is your favorite toy? Ever wanted to try a specific toy?
4- For a pet, Cat, dog or other?
76~ Have you had a threesome? Care to Share?
28- What are some things that people do that irritate you?
13- What’s your favorite drink? What’s your least favorite?
92~ Have you ever had or have an STD? How many? What was it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Escort/Client Job Applicant/Hiring Manager
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
14- What's your favorite dessert? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
The Ice Breaker Questions
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
34~ Do you like the lights on or off during sex?
*** Random Questions ***
33- Beach or Mountains? Or is there another place to like better?
11- How about if they like a certain sports team? 12-How about drinking too much?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
8- What are your thoughts on politics?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
22- Do you have any birth marks? How about scars? Care to share how you got them?
If yes, what?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
9- Is there something you’ve always wanted to ask me but you’re afraid?
37- Do you like your name? If you could change it, what would you change it too?
Any that are a turn off?
Do you watch it? What is your favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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)
40~ What’s the weirdest place you’ve ever had sex?
*** Deal Breaker Questions ***
17- Have you ever done drugs? Which ones? How often?
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?
12- What’s your favorite food? What’s your least 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?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
42~ What’s your biggest regret in life?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
11~ Have you ever been caught by your parents or children or others while having sex?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
30~ What's something unexpected that turns you on?
92~ Everyone needs a “safe” word. What is yours?
5~ When you first started having sex, was it what you thought it would be?
23- What is your dream job? What was it as a child?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
11- List at least 5 things on your bucket list. Have you done any of them already?
Do you like it when they show and tell you what they want?
13~ Is there a difference between, making love, having sex, and fucking?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Over time has your thoughts on sex changed?
12- What is the weirdest thing you've ever eaten?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Nurse/Patient Celebrity/Fan
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
62~ Have you used adult toys?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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?
65~ Describe the best orgasm you’ve ever had? Care to share?
Would you do it again, and would you rather 2 females or 2 males?
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,
How old are you? Male or Female?
82~ Do you have any fantasies involving Role-Playing?
How many partners have you had oral sex with? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
(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…)
What would you say to prove to yourself that it was really you?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Master/Slave Boss/Maid
1- What was your first impression of me? Has it changed?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
If YES, was it with 2 men or 2 women? Did you enjoy it?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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?
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
9~ How many times over your lifetime do you think you have had sex so far?
Model/Photographer Police/Criminal
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
* Give a rating for each one (0-100)
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Teacher/Student Stranger/One Night Stand
18~ Who/when was your first “crush”?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
61~ How willing would you be to try new sexual positions?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
44~ Care to share something about yourself that no one else knows about you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
3- What’s your favorite smell? Do you a least favorite?
83~ How do you feel about Porn?
What do you dislike about me? I asked you to be 100% honest.
21- What's your favorite way to spend a weekend or time off?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
53~ How much can you tell me about the one thing you are most passionate about?
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?
84~ How do you feel about reading/listening to adult stories?
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?
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
25~ How do you feel about PDA? (Public Display of Affection)
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
70~ Would/do you have/like anal sex?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Can you Deep Throat? Do you like the taste of yourself?
How well do you know me? And some of your thoughts about me
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
81~ Do you have any kinks and/or fetishes?
7-What do I do in bed that drives you wild? How about, what turns you off?
Please share Did you stop?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
7- What if a person smells a certain way? 8- How about smoking?
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…
*** Questions About Me ***
47~ What would be your dream job and why?
52~ Are you willing to make “those types” of bets with your partner?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Family Relation Age Play
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
50~ How many children do you have? What are their ages?
29~ What are some things that turn you off? What is your biggest turn off?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
*** What’s Your Favorite…? ***
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
22- What is your favorite childhood memory? What is your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
29- How superstitious are you?
Have you ever? Care to Share?
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?
18- How often do you drink alcohol? What is your favorite drink?
28~ What are some things that turn on? What is your biggest turn on?
Will you cheat again? How can, you be sure? Define what cheating is to you.
10- List 5 of your top pet peeves.
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
10~ How many dates are necessary before you to have sex with someone?
Does the thought excite you? Care to share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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?
48~ Have you ever paid or been paid for sex?
33- If you could visit any time period, when would you pick? Please explain why?
34- Ever been to a concert? What was your favorite? Who would you like to see?
What was the longest? What was the shortest?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Do you have a favorite? Is it ok if your partner does?
60~ How important is oral sex? Do you like receiving? Do you like giving?
15- What's your favorite saying? What word or phrase is your least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Would you read them together?
27- What was/ is nickname? Does it have a meaning behind it?
What have you learned about me that was new and/or surprising?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
71~ Would you give your partner a hand or foot job? Would you receive one?
32- What's your greatest talent? Can I see it right now?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Repairman/Lonely Wife Virgin/Experienced
38~ Share your most embarrassing sexual memory?
9- What’s your favorite season and why? What’s your least favorite?
What is your favorite position? Why?
9- If you could have three wishes, what would they be? Why?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Do you think this brought you closer together?
51~ Are you willing to play adult games with your partner?
6- Do you have dreams? Can you remember them? What do you usually dream about?
What is your view on sex? Meaning, When/Where/ How often/
If NO, would you ever have one? Would it be with 2 men or 2 women?
10- What is your favorite family tradition? What’s your least favorite?
13- How about having a certain hair cut/style?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
21~ What was the best date you ever went on? What has been the worst?
11- What's your favorite restaurant? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Doctor/Nurse Stripper/Client
Prisoner/Prison Guard Landlord/Tenant