What is the most interesting question you can ask to get to know someone?
08.06.2025 01:17
45~ How do you feel about me blindfolding you? How about blindfolding me?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Do very hot men ever feel attracted to an ugly woman? Why?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Over time has your thoughts on sex changed?
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?
Trump airs frustrations with Xi and Jerome Powell over elusive economic goals - NBC News
49~ How many times have you been married? Why did they end?
83~ How do you feel about Porn?
3- What’s your favorite smell? Do you a least favorite?
Brain ‘Reset Wave’ May Explain How ECT Rapidly Relieves Depression - Neuroscience News
11~ Have you ever been caught by your parents or children or others while having sex?
21~ What was the best date you ever went on? What has been the worst?
Nothing too Serious
52~ Are you willing to make “those types” of bets with your partner?
What is your view on sex? Meaning, When/Where/ How often/
80~ Share your top three fantasies/desires. (Be detailed) 😊
Do snipers lay on top of tank turrets during combat?
13~ Is there a difference between, making love, having sex, and fucking?
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?
FDA rushed out agency-wide AI tool—it’s not going well - Ars Technica
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
19- What’s your favorite fairytale? 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?
What’s something you did a lot as a kid that you don’t miss now that you’re an adult?
Would you do it again, and would you rather 2 females or 2 males?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
AI Is Upending the Job Market, Even at AI Companies Like Anthropic - Business Insider
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
Travis Kelce Salutes Taylor Swift for Buying Her Masters Back, 'It's Finally Hers' - Bleacher Report
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Please share Did you stop?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Can you write a short story with a twist ending?
48~ Do you have any siblings? Are you close to your family?
9~ How many times over your lifetime do you think you have had sex so far?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What is the most heartbreaking or sad love story that you ever had (experienced)?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
12- What’s your favorite food? 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…
82~ Do you have any fantasies involving Role-Playing?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
61~ How willing would you be to try new sexual positions?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Disney makes hundreds more layoffs as it cuts costs - BBC
Would you ever want to be woken up with oral and/or intercourse?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Do you have a favorite? Is it ok if your partner does?
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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Doctor/Nurse Stripper/Client
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
The Ice Breaker Questions
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
How about if they talk dirty and/or call you names?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Get this wrong and this could mean the end… :-) some funny, some not…
*** Questions about Relationships/Past ***
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
67~ Do you like it when your partner moans and/or is vocal during sex?
*** What’s Your Favorite…? ***
40~ What’s the weirdest place you’ve ever had sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
14- What is an embarrassing moment in your life? How about your most embarrassing?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Any that are a turn off?
18- How often do you drink alcohol? What is your favorite drink?
36~ What is your favorite time of day to have sex/make love?
Can you Deep Throat? Do you like the taste of yourself?
15- What bad habit do you wish you could quit? Do you have any addictions?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
60~ How important is oral sex? Do you like receiving? Do you like giving?
5~ When you first started having sex, was it what you thought it would be?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
If NO, would you ever have one? Would it be with 2 men or 2 women?
Would you read them together?
1- What’s your favorite animal? Do you a least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
19- Do/have you smoked? What do you prefer? How often?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
89~ Do you like taking showers together?
(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…)
28- What are some things that people do that irritate you?
What would you say to prove to yourself that it was really you?
38~ Share your most embarrassing sexual memory?
Would /have you ever given your partner a lap dance and Striptease?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
42~ What’s your biggest regret in life?
21- What's your favorite way to spend a weekend or time off?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
39~ What are your love languages?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
92~ Everyone needs a “safe” word. What is yours?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you watch it? What is your favorite?
47~ What would be your dream job and why?
65~ Describe the best orgasm you’ve ever had? Care to share?
17- Have you ever done drugs? Which ones? How often?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
How old are you? Male or Female?
Nurse/Patient Celebrity/Fan
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
9- If you could have three wishes, what would they be? Why?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
If you say it, I will stop, and we can talk about it when you are ready.
30~ What's something unexpected that turns you on?
9- What’s your favorite season and why? What’s your least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? 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?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
15~ Have you ever been “in love”? Who? Care to Share?
Does the thought excite you? Care to share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
48~ Have you ever paid or been paid for sex?
10- List 5 of your top pet peeves.
33- If you could visit any time period, when would you pick? Please explain why?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
56~ Would you ever go to a strip club with your partner? Have you ever been? 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?
28~ What are some things that turn on? What is your biggest turn on?
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,
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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?
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)
8- What's your favorite flavor of ice cream? Do you a least favorite?
18~ Who/when was your first “crush”?
That one or two things that made you go hmmmm, OMG or wow!
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
25~ How do you feel about PDA? (Public Display of Affection)
I would allow you to do it… What would you do to me?
How many times do you think you have “made love”?
What have you learned about yourself that you did not before this?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Repairman/Lonely Wife Virgin/Experienced
50~ How many children do you have? What are their ages?
22- Do you have any birth marks? How about scars? Care to share how you got them?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
*** Deal Breaker Questions ***
Family Relation Age Play
Would you mind if your partner watched it? How about together vs alone?
31- If given a chance to be immortal, would you take it? Why?
Escort/Client Job Applicant/Hiring Manager
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
How well do you know me? And some of your thoughts about me
70~ Would/do you have/like anal sex?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
81~ Do you have any kinks and/or fetishes?
20- What’s your favorite candy? What’s your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Do you think this brought you closer together?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
10~ How many dates are necessary before you to have sex with someone?
14- What's your favorite dessert? Do you a least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
62~ Have you used adult toys?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
You know that I will be 100% truthful, so ask.
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
84~ How do you feel about reading/listening to adult stories?
12- What is the weirdest thing you've ever eaten?
Prisoner/Prison Guard Landlord/Tenant
Any that are a turn off?
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)
26~ What side of the bed do you sleep on?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
76~ Have you had a threesome? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
23- What is your dream job? What was it as a child?
37- Do you like your name? If you could change it, what would you change it too?
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?
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?
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?
What have you learned about me that was new and/or surprising?
7- What if a person smells a certain way? 8- How about smoking?
10- What is your favorite family tradition? What’s your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What do you dislike about me? I asked you to be 100% honest.
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
13- How about having a certain hair cut/style?
Have you ever? Care to Share?
51~ Are you willing to play adult games with your partner?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Master/Slave Boss/Maid
34~ Do you like the lights on or off during sex?
If you win, what will you make them do?
What was the longest? What was the shortest?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
How many partners have you had oral sex with? Who? Care to Share?
If yes, what?
Model/Photographer Police/Criminal
51~ What tends to bring a smile to your face?
22- What is your favorite childhood memory? What is your least favorite?
29- How superstitious are you?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
11- List at least 5 things on your bucket list. Have you done any of them already?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
2- What’s your favorite color? Do you a least favorite?
8- What are your thoughts on politics?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
*** Random Questions ***
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
92~ Have you ever had or have an STD? How many? What was it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
13- What’s your favorite drink? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
19~ Who/when was your first “heartbreak”?
27- What was/ is nickname? Does it have a meaning behind it?
3- Should Pluto still be considered a planet? 4- How about smoking?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
7- What are your thoughts on religion? Is there an afterlife?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
32- What's your greatest talent? Can I see it right now?
71~ Would you give your partner a hand or foot job? Would you receive one?
52~ What are your hobbies?
53~ How much can you tell me about the one thing you are most passionate about?
Do you like it when they show and tell you what they want?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
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…
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
36- Do you play video games? What is your favorite? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
1- What was your first impression of me? Has it changed?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
33- Beach or Mountains? Or is there another place to like better?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
7-What do I do in bed that drives you wild? How about, what turns you off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
*** Questions About Me ***
4- For a pet, Cat, dog or other?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Teacher/Student Stranger/One Night Stand