What is the most interesting question you can ask to get to know someone?
11.06.2025 17:23
40~ What’s the weirdest place you’ve ever had sex?
Do you watch it? What is your favorite?
9- What’s your favorite season and why? What’s your least favorite?
Why has Biden pulled ahead in battleground states and is now projected to win the 2024 presidency?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What is your favorite toy? Ever wanted to try a specific toy?
84~ How do you feel about reading/listening to adult stories?
Report: Leafs discussed 3-way deal at deadline to send Marner to Vegas - theScore.com
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
I would allow you to do it… What would you do to me?
37- Do you like your name? If you could change it, what would you change it too?
Do you like it when they show and tell you what they want?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
83~ How do you feel about Porn?
67~ Do you like it when your partner moans and/or is vocal during sex?
1- What was your first impression of me? Has it changed?
29- How superstitious are you?
Escort/Client Job Applicant/Hiring Manager
Nurse/Patient Celebrity/Fan
3- What’s your favorite smell? Do you a least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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 is the weirdest thing you've ever eaten?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
I Discovered I Got Cheated On. But His Story About That Night Isn’t Adding Up. - Slate Magazine
50~ How many children do you have? What are their ages?
Do you like the “69” position? Do you prefer to be on top or bottom?
32- What's your greatest talent? Can I see it right now?
The ‘inexcusable’ mistake Knicks made again and again in season-ending loss - New York Post
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
* Give a rating for each one (0-100)
76~ Have you had a threesome? Care to Share?
Shortcuts is getting an AI-powered revamp; here’s what that could mean - 9to5Mac
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
3- What Superhero or Superpower would you want to be/have?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Trump signs proclamation banning travel from 12 countries - ABC News
11~ Have you ever been caught by your parents or children or others while having sex?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
15- What's your favorite saying? What word or phrase is your least favorite?
Saquon Barkley unveiled as ‘Madden NFL 26’ cover star with famous backwards hurdle - New York Post
15- What bad habit do you wish you could quit? Do you have any addictions?
9~ How many times over your lifetime do you think you have had sex so far?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Acting NASA Administrator Janet Petro June 6, 2025 - NASA Watch
Doctor/Nurse Stripper/Client
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
How well do you know me? And some of your thoughts about me
48~ Do you have any siblings? Are you close to your family?
What was the longest? What was the shortest?
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?
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?
10~ How many dates are necessary before you to have sex with someone?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
53~ How much can you tell me about the one thing you are most passionate about?
If yes, what?
13- What is the craziest/scariest thing you've ever done?
27- What was/ is nickname? Does it have a meaning behind it?
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?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
11- List at least 5 things on your bucket list. Have you done any of them already?
3- Should Pluto still be considered a planet? 4- How about smoking?
18- How often do you drink alcohol? What is your favorite drink?
25~ How do you feel about PDA? (Public Display of Affection)
51~ Are you willing to play adult games with your partner?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
38~ Share your most embarrassing sexual memory?
36~ What is your favorite time of day to have sex/make love?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
11- How about if they like a certain sports team? 12-How about drinking too much?
14- What's your favorite dessert? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
8- What are your thoughts on politics?
Nothing too Serious
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
28~ What are some things that turn on? What is your biggest turn on?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Do you have a favorite? Is it ok if your partner does?
26~ What side of the bed do you sleep on?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
20- What’s your favorite candy? What’s your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Would you mind if your partner watched it? How about together vs alone?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
(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…)
12- What’s your favorite food? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
34- Ever been to a concert? What was your favorite? Who would you like to see?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
62~ Have you used adult toys?
2- What’s your favorite color? Do you a least favorite?
Family Relation Age Play
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Over time has your thoughts on sex changed?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Would you read them together?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
52~ What are your hobbies?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
6- Do you have dreams? Can you remember them? What do you usually dream about?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Any that are a turn off?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
8- What's your favorite flavor of ice cream? Do you a least favorite?
7- What if a person smells a certain way? 8- How about smoking?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
1- What’s your favorite animal? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
Get this wrong and this could mean the end… :-) some funny, some not…
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
31- If given a chance to be immortal, would you take it? Why?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What is your view on sex? Meaning, When/Where/ How often/
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
19~ Who/when was your first “heartbreak”?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Does the thought excite you? Care to share?
15~ Have you ever been “in love”? Who? Care to Share?
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…
How many times do you think you have “made love”?
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?
21- What's your favorite way to spend a weekend or time 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)
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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,
22- What is your favorite childhood memory? What is your least favorite?
18~ Who/when was your first “crush”?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Model/Photographer Police/Criminal
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
What is your favorite position? Why?
51~ What tends to bring a smile to your face?
Any that are a turn off?
Prisoner/Prison Guard Landlord/Tenant
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
33- If you could visit any time period, when would you pick? Please explain why?
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?
9- Is there something you’ve always wanted to ask me but you’re afraid?
92~ Have you ever had or have an STD? How many? What was it?
19- Do/have you smoked? What do you prefer? How often?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What have you learned about yourself that you did not before this?
*** Random Questions ***
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
17- What’s your favorite holiday? What’s your least favorite?
81~ Do you have any kinks and/or fetishes?
How old are you? Male or Female?
5~ When you first started having sex, was it what you thought it would be?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What would you say to prove to yourself that it was really you?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Would you ever want to be woken up with oral and/or intercourse?
21~ What was the best date you ever went on? What has been the worst?
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?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
17- Have you ever done drugs? Which ones? How often?
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…
How many partners have you had oral sex with? Who? Care to Share?
47~ What would be your dream job and why?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
How about if they talk dirty and/or call you names?
5- Have you ever been hypnotized? Would you allow yourself to be?
60~ How important is oral sex? Do you like receiving? Do you like giving?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
1~ How old were you when you had your first kiss? Who? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
48~ Have you ever paid or been paid for sex?
28- What are some things that people do that irritate you?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
10- List 5 of your top pet peeves.
82~ Do you have any fantasies involving Role-Playing?
70~ Would/do you have/like anal sex?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
*** Deal Breaker Questions ***
If you say it, I will stop, and we can talk about it when you are ready.
34~ Do you like the lights on or off during sex?
Master/Slave Boss/Maid
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Repairman/Lonely Wife Virgin/Experienced
92~ Everyone needs a “safe” word. What is yours?
*** Questions about Relationships/Past ***
*** Questions About Me ***
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
33- Beach or Mountains? Or is there another place to like better?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What do you dislike about me? I asked you to be 100% honest.
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
49~ How many times have you been married? Why did they end?
65~ Describe the best orgasm you’ve ever had? Care to share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
You know that I will be 100% truthful, so ask.
What have you learned about me that was new and/or surprising?
The Ice Breaker Questions
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
89~ Do you like taking showers together?
42~ What’s your biggest regret in life?
39~ What are your love languages?
36- Do you play video games? What is your favorite? Do you a least favorite?
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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
13- What’s your favorite drink? What’s your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
13- How about having a certain hair cut/style?
10- What is your favorite family tradition? What’s your least favorite?
7- What are your thoughts on religion? Is there an afterlife?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
44~ Care to share something about yourself that no one else knows about you?
52~ Are you willing to make “those types” of bets with your partner?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
30~ What's something unexpected that turns you on?
4- For a pet, Cat, dog or other?
61~ How willing would you be to try new sexual positions?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
13~ Is there a difference between, making love, having sex, and fucking?
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?
Please share Did you stop?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Do you think this brought you closer together?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
23- What is your dream job? What was it as a child?
71~ Would you give your partner a hand or foot job? Would you receive one?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
*** What’s Your Favorite…? ***
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!
11- What's your favorite restaurant? What’s your least favorite?
If you win, what will you make them do?
Have you ever? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
9- If you could have three wishes, what would they be? Why?