What is the most interesting question you can ask to get to know someone?
Last Updated: 23.06.2025 05:01
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
51~ What tends to bring a smile to your face?
How well do you know me? And some of your thoughts about me
What are your thoughts on RM's new album "Right Place, Wrong Person"?
76~ Have you had a threesome? Care to Share?
28- What are some things that people do that irritate you?
13- What is the craziest/scariest thing you've ever done?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What was the longest? What was the shortest?
44~ Care to share something about yourself that no one else knows about you?
Have Dakota Johnson and Chris Martin Consciously Uncoupled? - The Cut
Would you ever want to be woken up with oral and/or intercourse?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Democrats be honest, how many of you were wishing that Musk rescue space flight blew up?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
11- List at least 5 things on your bucket list. Have you done any of them already?
When did you realize that your childhood was not normal?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
15~ Have you ever been “in love”? Who? Care to Share?
Do you share your food easily? With whom, and why?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
50~ How many children do you have? What are their ages?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Lisa Rinna and Donna Kelce to Have a Mother-Off on the Traitors Season 4 - Vulture
Get this wrong and this could mean the end… :-) some funny, some not…
13- How about having a certain hair cut/style?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Knicks’ coaching change could bring them everything they’re chasing - New York Post
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
Would /have you ever given your partner a lap dance and Striptease?
New study finds strong link between hearing loss and dementia - WKRC
1~ How old were you when you had your first kiss? Who? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would you do it again, and would you rather 2 females or 2 males?
Dementia risk begins in childhood, not old age, scientists warn - PsyPost
19- Do/have you smoked? What do you prefer? How often?
Family Relation Age Play
How many times do you think you have “made love”?
Do you think your landlord should have a key to your room?
52~ Are you willing to make “those types” of bets with your partner?
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?
29~ What are some things that turn you off? What is your biggest turn off?
Why did Microsoft acquire LinkedIn?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
5~ When you first started having sex, was it what you thought it would be?
10- What is your favorite family tradition? What’s your least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How about if they talk dirty and/or call you names?
12- What is the weirdest thing you've ever eaten?
Samsung could drop Google Gemini in favor of Perplexity for Galaxy S26 - Ars Technica
22- What is your favorite childhood memory? What is your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Why do I feel worthless most of the time?
Have you ever? Care to Share?
Doctor/Nurse Stripper/Client
34- Ever been to a concert? What was your favorite? Who would you like to see?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
52~ What are your hobbies?
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…
Do you shave/trim your pubic hair? For you guys do you shave your balls?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
92~ Have you ever had or have an STD? How many? What was it?
14- What is an embarrassing moment in your life? How about your most embarrassing?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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)
Do you have a favorite? Is it ok if your partner does?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
4- For a pet, Cat, dog or other?
If YES, was it with 2 men or 2 women? Did you enjoy it?
21- What's your favorite way to spend a weekend or time off?
84~ How do you feel about reading/listening to adult stories?
(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…)
Model/Photographer Police/Criminal
39~ What are your love languages?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Does the thought excite you? Care to share?
65~ Describe the best orgasm you’ve ever had? Care to share?
13- What’s your favorite drink? What’s your least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
How old are you? Male or Female?
3- Should Pluto still be considered a planet? 4- How about smoking?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
49~ How many times have you been married? Why did they end?
20- What’s your favorite candy? What’s your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
53~ How much can you tell me about the one thing you are most passionate about?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
18- How often do you drink alcohol? What is your favorite drink?
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?
48~ Do you have any siblings? Are you close to your family?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
11- What's your favorite restaurant? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
How many partners have you had oral sex with? Who? Care to Share?
Would you read them together?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
If yes, what?
Please share Did you stop?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
92~ Everyone needs a “safe” word. What is yours?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
11- How about if they like a certain sports team? 12-How about drinking too much?
Prisoner/Prison Guard Landlord/Tenant
7- What’s your favorite book? Do you have a favorite genre? Do you a 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?
Master/Slave Boss/Maid
9- What’s your favorite season and why? 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?
62~ Have you used adult toys?
9~ How many times over your lifetime do you think you have had sex so far?
Can you Deep Throat? Do you like the taste of yourself?
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…
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
5- Have you ever been hypnotized? Would you allow yourself to be?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? 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?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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?
What is your favorite toy? Ever wanted to try a specific toy?
7- What are your thoughts on religion? Is there an afterlife?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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?
7- What if a person smells a certain way? 8- How about smoking?
1- What was your first impression of me? Has it changed?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
42~ What’s your biggest regret in life?
32- What's your greatest talent? Can I see it right now?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
* Give a rating for each one (0-100)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
1- What’s your favorite animal? Do you a least favorite?
23- What is your dream job? What was it as a child?
29- How superstitious are you?
Any that are a turn off?
I would allow you to do it… What would you do to me?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
19~ Who/when was your first “heartbreak”?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
9- Is there something you’ve always wanted to ask me but you’re afraid?
If NO, would you ever have one? Would it be with 2 men or 2 women?
The Ice Breaker Questions
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
3- What Superhero or Superpower would you want to be/have?
Nurse/Patient Celebrity/Fan
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
30~ What's something unexpected that turns you on?
71~ Would you give your partner a hand or foot job? Would you receive one?
2- What’s your favorite color? Do you a least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
10- List 5 of your top pet peeves.
Any that are a turn off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Will you cheat again? How can, you be sure? Define what cheating is to you.
9- If you could have three wishes, what would they be? Why?
17- Have you ever done drugs? Which ones? How often?
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?
10~ How many dates are necessary before you to have sex with someone?
If you win, what will you make them do?
48~ Have you ever paid or been paid for sex?
15- What's your favorite saying? What word or phrase is your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
83~ How do you feel about Porn?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
3- What’s your favorite smell? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
22- Do you have any birth marks? How about scars? Care to share how you got them?
14- What's your favorite dessert? Do you a least favorite?
47~ What would be your dream job and why?
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?
If you say it, I will stop, and we can talk about it when you are ready.
Nothing too Serious
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
*** What’s Your Favorite…? ***
18~ Who/when was your first “crush”?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
27- What was/ is nickname? Does it have a meaning behind it?
15- What bad habit do you wish you could quit? Do you have any addictions?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
21~ What was the best date you ever went on? What has been the worst?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
33- If you could visit any time period, when would you pick? Please explain why?
What would you say to prove to yourself that it was really you?
51~ Are you willing to play adult games with your partner?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
28~ What are some things that turn on? What is your biggest turn on?
81~ Do you have any kinks and/or fetishes?
What is your view on sex? Meaning, When/Where/ How often/
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
31- If given a chance to be immortal, would you take it? Why?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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,
*** Questions about Relationships/Past ***
8- What are your thoughts on politics?
60~ How important is oral sex? Do you like receiving? Do you like giving?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
34~ Do you like the lights on or off during sex?
What have you learned about me that was new and/or surprising?
36~ What is your favorite time of day to have sex/make love?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
12- What’s your favorite food? What’s your least favorite?
17- What’s your favorite holiday? What’s your least favorite?
33- Beach or Mountains? Or is there another place to like better?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Would you mind if your partner watched it? How about together vs alone?
26~ What side of the bed do you sleep on?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
70~ Would/do you have/like anal sex?
Teacher/Student Stranger/One Night Stand
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
38~ Share your most embarrassing sexual memory?
*** Deal Breaker Questions ***
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
24~ What are your expectations in a relationship? (I know a very big question, take your time)
What is your favorite position? 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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Escort/Client Job Applicant/Hiring Manager
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Repairman/Lonely Wife Virgin/Experienced
19- What’s your favorite fairytale? What’s your least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What do you dislike about me? I asked you to be 100% honest.
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Do you watch it? What is your favorite?
40~ What’s the weirdest place you’ve ever had sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
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?
Do you think this brought you closer together?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
That one or two things that made you go hmmmm, OMG or wow!
13~ Is there a difference between, making love, having sex, and fucking?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
37- Do you like your name? If you could change it, what would you change it too?
82~ Do you have any fantasies involving Role-Playing?
Do you like it when they show and tell you what they want?
25~ How do you feel about PDA? (Public Display of Affection)
89~ Do you like taking showers together?
11~ Have you ever been caught by your parents or children or others while having sex?
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?
67~ Do you like it when your partner moans and/or is vocal during sex?
You know that I will be 100% truthful, so ask.
80~ Share your top three fantasies/desires. (Be detailed) 😊
What have you learned about yourself that you did not before this?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
61~ How willing would you be to try new sexual positions?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
*** Questions About Me ***
*** Random Questions ***
Over time has your thoughts on sex changed?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?