What is the most interesting question you can ask to get to know someone?
Last Updated: 22.06.2025 00:56
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
When it's time to think about AI for recruitment process automation?
What have you learned about me that was new and/or surprising?
If you win, what will you make them do?
Have you ever? Care to Share?
Brain Uses Separate Synapses to Balance Learning and Stability - Neuroscience News
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
What species of fish are horse mackerels?
Do you have a favorite? Is it ok if your partner does?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
ABC News anchor David Muir reveals how he feels about his 'Daddy' status - Entertainment Weekly
19- Do/have you smoked? What do you prefer? How often?
2- What’s your favorite color? 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?
Nothing too Serious
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
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?
Why are people nowadays so into anal sex?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
67~ Do you like it when your partner moans and/or is vocal during sex?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Alex Cooper Accuses Former Soccer Coach of Sexual Harassment in Call Her Alex - Vulture
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Over time has your thoughts on sex changed?
7- What if a person smells a certain way? 8- How about smoking?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Model/Photographer Police/Criminal
10- What is your favorite family tradition? What’s your least favorite?
Are you offended if Democrats call Republicans "weird"?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
36~ What is your favorite time of day to have sex/make love?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
*** Questions About Me ***
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
*** Questions about Relationships/Past ***
49~ How many times have you been married? Why did they end?
40~ What’s the weirdest place you’ve ever had sex?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Please share Did you stop?
1~ How old were you when you had your first kiss? Who? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
12- What’s your favorite food? What’s your least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
3- What Superhero or Superpower would you want to be/have?
25~ How do you feel about PDA? (Public Display of Affection)
89~ Do you like taking showers together?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
17- Have you ever done drugs? Which ones? How often?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
70~ Would/do you have/like anal sex?
*** Random Questions ***
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How old are you? Male or Female?
Any that are a turn off?
42~ What’s your biggest regret in life?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
8- What are your thoughts on politics?
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?
33- Beach or Mountains? Or is there another place to like better?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
How many times do you think you have “made love”?
Can you Deep Throat? Do you like the taste of yourself?
14- What's your favorite dessert? Do you a least favorite?
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?
20- What’s your favorite candy? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
What have you learned about yourself that you did not before this?
Escort/Client Job Applicant/Hiring Manager
34- Ever been to a concert? What was your favorite? Who would you like to see?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
13- What’s your favorite drink? What’s your least favorite?
52~ What are your hobbies?
10- List 5 of your top pet peeves.
9- What’s your favorite season and why? What’s your least favorite?
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?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Would you do it again, and would you rather 2 females or 2 males?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
47~ What would be your dream job and why?
Get this wrong and this could mean the end… :-) some funny, some not…
83~ How do you feel about Porn?
Any that are a turn off?
10~ How many dates are necessary before you to have sex with someone?
23- What is your dream job? What was it as a child?
39~ What are your love languages?
28- What are some things that people do that irritate you?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
18~ Who/when was your first “crush”?
92~ Have you ever had or have an STD? How many? What was it?
I would allow you to do it… What would you do to me?
What do you dislike about me? I asked you to be 100% honest.
29- How superstitious are you?
If YES, was it with 2 men or 2 women? Did you enjoy it?
You know that I will be 100% truthful, so ask.
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Would you ever want to be woken up with oral and/or intercourse?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
33- If you could visit any time period, when would you pick? Please explain why?
Would you allow me to clean every part of your body with my soapy hands and fingers?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
13- How about having a certain hair cut/style?
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?
81~ Do you have any kinks and/or fetishes?
32- What's your greatest talent? Can I see it right now?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
62~ Have you used adult toys?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
The Ice Breaker Questions
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)
48~ Do you have any siblings? Are you close to your family?
How many partners have you had oral sex with? Who? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
22- Do you have any birth marks? How about scars? Care to share how you got them?
* Give a rating for each one (0-100)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
1- What was your first impression of me? Has it changed?
9~ How many times over your lifetime do you think you have had sex so far?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
51~ What tends to bring a smile to your face?
Prisoner/Prison Guard Landlord/Tenant
48~ Have you ever paid or been paid for sex?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
36- Do you play video games? What is your favorite? Do you a least favorite?
5~ When you first started having sex, was it what you thought it would be?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
22- What is your favorite childhood memory? What is your least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? 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…)
37- Do you like your name? If you could change it, what would you change it too?
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…
3- What’s your favorite smell? Do you a least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What’s the longest time you gone without having sex, after, having it? How much time between the others?
19~ Who/when was your first “heartbreak”?
That one or two things that made you go hmmmm, OMG or wow!
How about if they talk dirty and/or call you names?
84~ How do you feel about reading/listening to adult stories?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
60~ How important is oral sex? Do you like receiving? Do you like giving?
5- Have you ever been hypnotized? Would you allow yourself to be?
What is your favorite position? Why?
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…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
What was the longest? What was the shortest?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
61~ How willing would you be to try new sexual positions?
18- How often do you drink alcohol? What is your favorite drink?
Doctor/Nurse Stripper/Client
What is your view on sex? Meaning, When/Where/ How often/
12- What is the weirdest thing you've ever eaten?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
*** Deal Breaker Questions ***
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
3- Should Pluto still be considered a planet? 4- How about smoking?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
15~ Have you ever been “in love”? Who? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
30~ What's something unexpected that turns you on?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
How well do you know me? And some of your thoughts about me
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?
26~ What side of the bed do you sleep on?
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?
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?
13- What is the craziest/scariest thing you've ever done?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Does the thought excite you? Care to share?
27- What was/ is nickname? Does it have a meaning behind it?
Would you mind if your partner watched it? How about together vs alone?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
53~ How much can you tell me about the one thing you are most passionate about?
Teacher/Student Stranger/One Night Stand
44~ Care to share something about yourself that no one else knows about you?
Do you watch it? What is your favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
17- What’s your favorite holiday? What’s your least favorite?
38~ Share your most embarrassing sexual memory?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Would /have you ever given your partner a lap dance and Striptease?
11- What's your favorite restaurant? What’s your least 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,
If yes, what?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Do you like it when they show and tell you what they want?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Do you think this brought you closer together?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Family Relation Age Play
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
8- What's your favorite flavor of ice cream? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
29~ What are some things that turn you off? What is your biggest turn off?
Would you read them together?
13~ Is there a difference between, making love, having sex, and fucking?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7- What are your thoughts on religion? Is there an afterlife?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
31- If given a chance to be immortal, would you take it? Why?
What is your favorite toy? Ever wanted to try a specific toy?
7-What do I do in bed that drives you wild? How about, what turns you off?
1- What’s your favorite animal? Do you a least 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?
11~ Have you ever been caught by your parents or children or others while having sex?
15- What bad habit do you wish you could quit? Do you have any addictions?
Repairman/Lonely Wife Virgin/Experienced
92~ Everyone needs a “safe” word. What is yours?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
71~ Would you give your partner a hand or foot job? Would you receive one?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
76~ Have you had a threesome? Care to Share?
50~ How many children do you have? What are their ages?
Nurse/Patient Celebrity/Fan
If NO, would you ever have one? Would it be with 2 men or 2 women?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
Master/Slave Boss/Maid
34~ Do you like the lights on or off during sex?
What would you say to prove to yourself that it was really 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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
If you say it, I will stop, and we can talk about it when you are ready.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Do you like the “69” position? Do you prefer to be on top or bottom?
52~ Are you willing to make “those types” of bets with your partner?
51~ Are you willing to play adult games with your partner?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
*** What’s Your Favorite…? ***
28~ What are some things that turn on? What is your biggest turn on?
65~ Describe the best orgasm you’ve ever had? Care to share?