What is the most interesting question you can ask to get to know someone?
Last Updated: 23.06.2025 11:30
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would you read them together?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
42~ What’s your biggest regret in life?
62~ Have you used adult toys?
What are some examples of unofficial acts by presidents?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
14- What's your favorite dessert? Do you a least favorite?
What have you learned about yourself that you did not before this?
13- How about having a certain hair cut/style?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
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?
Bikini-clad Brooke Shields celebrates milestone birthday on beach vacation: ‘This is 60!’ - Page Six
80~ Share your top three fantasies/desires. (Be detailed) 😊
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
19- Do/have you smoked? What do you prefer? How often?
Over time has your thoughts on sex changed?
The Ice Breaker Questions
Get this wrong and this could mean the end… :-) some funny, some not…
Apple is on defense at WWDC 2025 - The Verge
Nothing too Serious
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Please share Did you stop?
Panthers' winning formula goes missing in Stanley Cup Final Game 1 loss to Oilers - NHL.com
Does the thought excite you? Care to share?
Would you ever want to be woken up with oral and/or intercourse?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What is the best case of “You just picked a fight with the wrong person” that you've witnessed?
11- What's your favorite restaurant? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Mario Kart World tech analysis, including frame rate and resolution - Nintendo Everything
What would you say to prove to yourself that it was really you?
39~ What are your love languages?
That one or two things that made you go hmmmm, OMG or wow!
Childhood infections, stress may increase MS risk: Study - Multiple Sclerosis News Today
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
If you say it, I will stop, and we can talk about it when you are ready.
Would you mind if your partner watched it? How about together vs alone?
It's time to make friends with your viruses - Salon.com
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Model/Photographer Police/Criminal
10~ How many dates are necessary before you to have sex with someone?
49~ How many times have you been married? Why did they end?
Pokémon Go Serene Retreat Collection Challenges and rewards - Eurogamer
How many partners have you had oral sex with? Who? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
How old are you? Male or Female?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Do you have a favorite? Is it ok if your partner does?
How do you emotionally react to when others seem to feel sorry for you?
40~ What’s the weirdest place you’ve ever had sex?
If yes, what?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
5- Have you ever been hypnotized? Would you allow yourself to be?
33- If you could visit any time period, when would you pick? Please explain why?
81~ Do you have any kinks and/or fetishes?
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?
82~ Do you have any fantasies involving Role-Playing?
28~ What are some things that turn on? What is your biggest turn on?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Family Relation Age Play
51~ Are you willing to play adult games with your partner?
If YES, was it with 2 men or 2 women? Did you enjoy it?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
4- For a pet, Cat, dog or other?
2- What’s your favorite color? Do you a least favorite?
1- What was your first impression of me? Has it changed?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
29- How superstitious are you?
Have you ever? Care to Share?
3- What Superhero or Superpower would you want to be/have?
How many times do you think you have “made love”?
What have you learned about me that was new and/or surprising?
Any that are a turn off?
*** Questions about Relationships/Past ***
Teacher/Student Stranger/One Night Stand
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you allow me to clean every part of your body with my soapy hands and fingers?
What is your favorite toy? Ever wanted to try a specific toy?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
67~ Do you like it when your partner moans and/or is vocal during sex?
89~ Do you like taking showers together?
83~ How do you feel about Porn?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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?
70~ Would/do you have/like anal sex?
Prisoner/Prison Guard Landlord/Tenant
84~ How do you feel about reading/listening to adult stories?
28- What are some things that people do that irritate you?
Would you do it again, and would you rather 2 females or 2 males?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
9- What’s your favorite season and why? What’s your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Do you think this brought you closer together?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
8- What are your thoughts on politics?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
19- What’s your favorite fairytale? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
8- What's your favorite flavor of ice cream? 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?
9- If you could have three wishes, what would they be? Why?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
48~ Do you have any siblings? Are you close to your family?
10- List 5 of your top pet peeves.
Master/Slave Boss/Maid
Can you Deep Throat? Do you like the taste of yourself?
20- What’s your favorite candy? What’s your least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
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~ What are you best at in bed? What do you think you are not so good at? Anything you want to get good at?
76~ Have you had a threesome? Care to Share?
Escort/Client Job Applicant/Hiring Manager
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Do you like the “69” position? Do you prefer to be on top or bottom?
How about if they talk dirty and/or call you names?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
17- What’s your favorite holiday? What’s your least favorite?
18~ Who/when was your first “crush”?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
17- Have you ever done drugs? Which ones? How often?
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?
How well do you know me? And some of your thoughts about me
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…
21~ What was the best date you ever went on? What has been the worst?
61~ How willing would you be to try new sexual positions?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
38~ Share your most embarrassing sexual memory?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
36~ What is your favorite time of day to have sex/make love?
22- Do you have any birth marks? How about scars? Care to share how you got them?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Repairman/Lonely Wife Virgin/Experienced
60~ How important is oral sex? Do you like receiving? Do you like giving?
*** Deal Breaker Questions ***
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Do you like it when they show and tell you what they want?
21- What's your favorite way to spend a weekend or time off?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
3- Should Pluto still be considered a planet? 4- How about smoking?
18- How often do you drink alcohol? What is your favorite drink?
5~ When you first started having sex, was it what you thought it would be?
31- If given a chance to be immortal, would you take it? Why?
If NO, would you ever have one? Would it be with 2 men or 2 women?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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,
92~ Everyone needs a “safe” word. What is yours?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
You know that I will be 100% truthful, so ask.
3- What’s your favorite smell? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
30~ What's something unexpected that turns you on?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Any that are a turn off?
7- What if a person smells a certain way? 8- How about smoking?
12- What is the weirdest thing you've ever eaten?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
13- What’s your favorite drink? What’s 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?
44~ Care to share something about yourself that no one else knows about you?
1~ How old were you when you had your first kiss? Who? Care to Share?
23- What is your dream job? What was it as a child?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
15~ Have you ever been “in love”? Who? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
11~ Have you ever been caught by your parents or children or others while having sex?
If you win, what will you make them do?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Nurse/Patient Celebrity/Fan
*** Questions About Me ***
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
51~ What tends to bring a smile to your face?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
(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…)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
7-What do I do in bed that drives you wild? How about, what turns you off?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
14- What is an embarrassing moment in your life? How about your most embarrassing?
7- What are your thoughts on religion? Is there an afterlife?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
45~ How do you feel about me blindfolding you? How about blindfolding me?
52~ Are you willing to make “those types” of bets with your partner?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
32- What's your greatest talent? Can I see it right now?
12- What’s your favorite food? What’s your least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
71~ Would you give your partner a hand or foot job? Would you receive one?
Would /have you ever given your partner a lap dance and Striptease?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
11- How about if they like a certain sports team? 12-How about drinking too much?
47~ What would be your dream job and why?
19~ Who/when was your first “heartbreak”?
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?
53~ How much can you tell me about the one thing you are most passionate about?
1- What’s your favorite animal? Do you a least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
65~ Describe the best orgasm you’ve ever had? Care to share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
13- What is the craziest/scariest thing you've ever done?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
What do you dislike about me? I asked you to be 100% honest.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
What is your favorite position? Why?
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?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
34~ Do you like the lights on or off during sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
33- Beach or Mountains? Or is there another place to like better?
92~ Have you ever had or have an STD? How many? What was it?
36- Do you play video games? What is your favorite? Do you a least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
26~ What side of the bed do you sleep on?
Doctor/Nurse Stripper/Client
37- Do you like your name? If you could change it, what would you change it too?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
50~ How many children do you have? What are their ages?
*** Random Questions ***
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
* Give a rating for each one (0-100)
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
25~ How do you feel about PDA? (Public Display of Affection)
52~ What are your hobbies?
29~ What are some things that turn you off? What is your biggest turn off?
48~ Have you ever paid or been paid for sex?
13~ Is there a difference between, making love, having sex, and fucking?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Do you watch it? What is your favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
I would allow you to do it… What would you do to me?
*** What’s Your Favorite…? ***
What is your view on sex? Meaning, When/Where/ How often/
What was the longest? What was the shortest?
22- What is your favorite childhood memory? What is your least favorite?