What is the most interesting question you can ask to get to know someone?
08.06.2025 16:11
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How old are you? Male or Female?
Live Updates: FSU 5, Miss. St. 2 -- FINAL - 247Sports
Can you Deep Throat? Do you like the taste of yourself?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
How is digital marketing important for business?
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)
17- Have you ever done drugs? Which ones? How often?
12- What’s your favorite food? What’s your least favorite?
Reds star Elly De La Cruz homers after learning of the death of his sister - AP News
48~ Do you have any siblings? Are you close to your family?
Will you cheat again? How can, you be sure? Define what cheating is to you.
14- What is an embarrassing moment in your life? How about your most embarrassing?
Liam Coen: I think Trevor Lawrence’s footwork has drastically improved - NBC Sports
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
7- What are your thoughts on religion? Is there an afterlife?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
37- Do you like your name? If you could change it, what would you change it too?
8- What are your thoughts on politics?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
26~ What side of the bed do you sleep on?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What are some reasons why men may not want to date a woman who can pay her own bills?
Nothing too Serious
46~ Have you ever used furniture, or other types of things to aid you while having sex?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How do I run away? I'm 15 and live in Oklahoma.
19~ Who/when was your first “heartbreak”?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
11~ Have you ever been caught by your parents or children or others while having sex?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
Neuroscience breakthroughs: Surprising truths about memory revealed in 7 recent studies - PsyPost
10- What is your favorite family tradition? What’s your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
Precision Spectroscopy Reaffirms Gap Between Theory and Experiment - American Physical Society
53~ How much can you tell me about the one thing you are most passionate about?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
67~ Do you like it when your partner moans and/or is vocal during sex?
11- What's your favorite restaurant? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Why do old men think young women and girls would want them over guys their own age?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
*** What’s Your Favorite…? ***
Please share Did you stop?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
Escort/Client Job Applicant/Hiring Manager
What have you learned about me that was new and/or surprising?
20- What’s your favorite candy? What’s your least favorite?
How about if they talk dirty and/or call you names?
Nurse/Patient Celebrity/Fan
How many times do you think you have “made love”?
8- What's your favorite flavor of ice cream? Do you a least favorite?
28- What are some things that people do that irritate you?
52~ What are your hobbies?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
4- For a pet, Cat, dog or other?
13- How about having a certain hair cut/style?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Teacher/Student Stranger/One Night Stand
15- What bad habit do you wish you could quit? Do you have any addictions?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
39~ What are your love languages?
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?
If you win, what will you make them do?
* Give a rating for each one (0-100)
9- If you could have three wishes, what would they be? Why?
21~ What was the best date you ever went on? What has been the worst?
40~ What’s the weirdest place you’ve ever had sex?
42~ What’s your biggest regret in life?
If NO, would you ever have one? Would it be with 2 men or 2 women?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
52~ Are you willing to make “those types” of bets with your partner?
13- What is the craziest/scariest thing you've ever done?
What was the longest? What was the shortest?
50~ How many children do you have? What are their ages?
Family Relation Age Play
Repairman/Lonely Wife Virgin/Experienced
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
That one or two things that made you go hmmmm, OMG or wow!
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
I would allow you to do it… What would you do to me?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
11- List at least 5 things on your bucket list. Have you done any of them already?
47~ What would be your dream job and why?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
80~ Share your top three fantasies/desires. (Be detailed) 😊
10- List 5 of your top pet peeves.
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?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Does the thought excite you? Care to share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
31- If given a chance to be immortal, would you take it? Why?
*** Questions About Me ***
23- What is your dream job? What was it as a child?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
19- Do/have you smoked? What do you prefer? How often?
Do you like the “69” position? Do you prefer to be on top or bottom?
Any that are a turn off?
If you say it, I will stop, and we can talk about it when you are ready.
33- Beach or Mountains? Or is there another place to like better?
What is your favorite position? Why?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
The Ice Breaker Questions
Over time has your thoughts on sex changed?
7- What if a person smells a certain way? 8- How about smoking?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
13- What’s your favorite drink? What’s your least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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?
7-What do I do in bed that drives you wild? How about, what turns you off?
10~ How many dates are necessary before you to have sex with someone?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
5- Have you ever been hypnotized? Would you allow yourself to be?
15~ Have you ever been “in love”? Who? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Do you think this brought you closer together?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
29- How superstitious are you?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
44~ Care to share something about yourself that no one else knows about you?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
51~ Are you willing to play adult games with your partner?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
92~ Have you ever had or have an STD? How many? What was it?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
*** Questions about Relationships/Past ***
Will you kiss after your partner has gone down on you? Swallow or spit semen?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
12- What is the weirdest thing you've ever eaten?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you watch it? What is your favorite?
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,
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
How many partners have you had oral sex with? Who? Care to Share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
48~ Have you ever paid or been paid for sex?
70~ Would/do you have/like anal sex?
Any that are a turn off?
81~ Do you have any kinks and/or fetishes?
Do you like it when they show and tell you what they want?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
32- What's your greatest talent? Can I see it right now?
2- What’s your favorite color? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
22- What is your favorite childhood memory? What is your least favorite?
3- What Superhero or Superpower would you want to be/have?
30~ What's something unexpected that turns you on?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
38~ Share your most embarrassing sexual memory?
How well do you know me? And some of your thoughts about me
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
13~ Is there a difference between, making love, having sex, and fucking?
What do you dislike about me? I asked you to be 100% honest.
What’s the longest time you gone without having sex, after, having it? How much time between the others?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
36- Do you play video games? What is your favorite? Do you a least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
6- Do you have dreams? Can you remember them? What do you usually dream about?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
62~ Have you used adult toys?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Would you mind if your partner watched it? How about together vs alone?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
92~ Everyone needs a “safe” word. What is yours?
You know that I will be 100% truthful, so ask.
28~ What are some things that turn on? What is your biggest turn on?
51~ What tends to bring a smile to your face?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
36~ What is your favorite time of day to have sex/make love?
1- What’s your favorite animal? Do you a least favorite?
Master/Slave Boss/Maid
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
*** Deal Breaker Questions ***
3- Should Pluto still be considered a planet? 4- How about smoking?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Have you ever? Care to Share?
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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
*** Random Questions ***
84~ How do you feel about reading/listening to adult stories?
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?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
18- How often do you drink alcohol? What is your favorite drink?
25~ How do you feel about PDA? (Public Display of Affection)
9- Is there something you’ve always wanted to ask me but you’re afraid?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
61~ How willing would you be to try new sexual positions?
Would you ever want to be woken up with oral and/or intercourse?
1~ How old were you when you had your first kiss? Who? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
What is your favorite toy? Ever wanted to try a specific toy?
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?
What would you say to prove to yourself that it was really you?
34- Ever been to a concert? What was your favorite? Who would you like to see?
76~ Have you had a threesome? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
82~ Do you have any fantasies involving Role-Playing?
45~ How do you feel about me blindfolding you? How about blindfolding me?
34~ Do you like the lights on or off during sex?
49~ How many times have you been married? Why did they end?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Doctor/Nurse Stripper/Client
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you read them together?
If yes, what?
What have you learned about yourself that you did not before this?
83~ How do you feel about Porn?
21- What's your favorite way to spend a weekend or time off?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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…
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
27- What was/ is nickname? Does it have a meaning behind it?
17- What’s your favorite holiday? What’s your least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
18~ Who/when was your first “crush”?
1- What was your first impression of me? Has it changed?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
15- What's your favorite saying? What word or phrase is your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would you do it again, and would you rather 2 females or 2 males?
60~ How important is oral sex? Do you like receiving? Do you like giving?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
(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 is your view on sex? Meaning, When/Where/ How often/
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
89~ Do you like taking showers together?
3- What’s your favorite smell? Do you a least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
11- How about if they like a certain sports team? 12-How about drinking too much?
Model/Photographer Police/Criminal
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
33- If you could visit any time period, when would you pick? Please explain why?
Prisoner/Prison Guard Landlord/Tenant
22- Do you have any birth marks? How about scars? Care to share how you got them?
5~ When you first started having sex, was it what you thought it would be?
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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
65~ Describe the best orgasm you’ve ever had? Care to share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?