What is the most interesting question you can ask to get to know someone?
Last Updated: 28.06.2025 00:00
52~ What are your hobbies?
80~ Share your top three fantasies/desires. (Be detailed) đ
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
The Gears of War Reloaded beta is here, what you need to know and how to play - Windows Central
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Would you ever want to be woken up with oral and/or intercourse?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
L.A. Dodgers, facing fan pressure, pledge $1M after immigration raids - The Washington Post
Prisoner/Prison Guard Landlord/Tenant
14- What is an embarrassing moment in your life? How about your most embarrassing?
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
A Glucose Monitor for Someone Without Diabetes: Optimal or Overkill? - WSJ
If yes, what?
53~ How much can you tell me about the one thing you are most passionate about?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
26~ What side of the bed do you sleep on?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
How many times do you think you have âmade loveâ?
The Mustangâs New Appearance Pack Is a 1980s Fever Dream - Motor1.com
28- What are some things that people do that irritate you?
Please share Did you stop?
48~ Do you have any siblings? Are you close to your family?
19~ Who/when was your first âheartbreakâ?
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
Why We Still Can't Find A Solar System Twin - IFLScience
10- List 5 of your top pet peeves.
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
How can reading fiction be turned from escapism into personal growth?
What have you learned about yourself that you did not before this?
Escort/Client Job Applicant/Hiring Manager
31- If given a chance to be immortal, would you take it? Why?
What is the best TV to consider from an interior design perspective?
*** Questions About Me ***
Over time has your thoughts on sex changed?
What have you learned about me that was new and/or surprising?
What is the best comeback you used on someone?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
1- Whatâs your favorite animal? Do you a least favorite?
*** Questions about Relationships/Past ***
52~ Are you willing to make âthose typesâ of bets with your partner?
Would you mind if your partner watched it? How about together vs alone?
Any that are a turn off?
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?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
The Ice Breaker Questions
6- Do you have dreams? Can you remember them? What do you usually dream about?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
If you say it, I will stop, and we can talk about it when you are ready.
85~ If I gave you a âFree Passâ for you to do anything to me for one hour, knowing that no matter what you did,
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
11- How about if they like a certain sports team? 12-How about drinking too much?
27- What was/ is nickname? Does it have a meaning behind it?
23- What is your dream job? What was it as a child?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
92~ Have you ever had or have an STD? How many? What was it?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
*** Random Questions ***
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
71~ Would you give your partner a hand or foot job? Would you receive one?
3- What Superhero or Superpower would you want to be/have?
49~ How many times have you been married? Why did they end?
14 â Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
83~ How do you feel about Porn?
15~ Have you ever been âin loveâ? Who? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
That one or two things that made you go hmmmm, OMG or wow!
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
3- What was the most surprising thing youâve learned about me throughout our relationship?
Do you like the â69â position? Do you prefer to be on top or bottom?
*** Deal Breaker Questions ***
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
9~ How many times over your lifetime do you think you have had sex so far?
28~ What are some things that turn on? What is your biggest turn on?
36~ What is your favorite time of day to have sex/make love?
39~ What are your love languages?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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)
* Give a rating for each one (0-100)
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 togetherâŚ
60~ How important is oral sex? Do you like receiving? Do you like giving?
2- Whatâs your favorite color? Do you a least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
10~ How many dates are necessary before you to have sex with someone?
Do you think this brought you closer together?
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
If you win, what will you make them do?
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 position? Why?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would you do it again, and would you rather 2 females or 2 males?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
51~ Are you willing to play adult games with your partner?
Doctor/Nurse Stripper/Client
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Have you ever? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
48~ Have you ever paid or been paid for sex?
How old are you? Male or Female?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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?
13- How about having a certain hair cut/style?
7- What are your thoughts on religion? Is there an afterlife?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
15- What's your favorite saying? What word or phrase is your least favorite?
3- Whatâs your favorite smell? Do you a least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
13- What is the craziest/scariest thing you've ever done?
What would you say to prove to yourself that it was really you?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŚ
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
10- What is your favorite family tradition? Whatâs your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
11- What's your favorite restaurant? Whatâs your least favorite?
47~ What would be your dream job and why?
9- Is there something youâve always wanted to ask me but youâre afraid?
Would you read them together?
42~ Whatâs your biggest regret in life?
22- What is your favorite childhood memory? What is your least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
9- If you could have three wishes, what would they be? Why?
11- List at least 5 things on your bucket list. Have you done any of them already?
51~ What tends to bring a smile to your face?
81~ Do you have any kinks and/or fetishes?
Teacher/Student Stranger/One Night Stand
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
21- What's your favorite way to spend a weekend or time off?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
38~ Share your most embarrassing sexual memory?
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couplesâ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETCâŚ)
18- How often do you drink alcohol? What is your favorite drink?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Repairman/Lonely Wife Virgin/Experienced
If YES, was it with 2 men or 2 women? Did you enjoy it?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
Nothing too Serious
1~ How old were you when you had your first kiss? Who? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
17- Have you ever done drugs? Which ones? How often?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
92~ Everyone needs a âsafeâ word. What is yours?
19- Do/have you smoked? What do you prefer? How often?
36- Do you play video games? What is your favorite? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Master/Slave Boss/Maid
8- What are your thoughts on politics?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
18~ Who/when was your first âcrushâ?
Get this wrong and this could mean the end⌠:-) some funny, some notâŚ
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
44~ Care to share something about yourself that no one else knows about you?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
5~ When you first started having sex, was it what you thought it would be?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you have a favorite? Is it ok if your partner does?
7- What if a person smells a certain way? 8- How about smoking?
17- Whatâs your favorite holiday? Whatâs your least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Can you Deep Throat? Do you like the taste of yourself?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
34~ Do you like the lights on or off during sex?
How about if they talk dirty and/or call you names?
70~ Would/do you have/like anal sex?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
I would allow you to do it⌠What would you do to me?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
89~ Do you like taking showers together?
8- What's your favorite flavor of ice cream? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
13- Whatâs your favorite drink? Whatâs your least favorite?
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 âPASSâ 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 yourselfâŚ
82~ Do you have any fantasies involving Role-Playing?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
*** Whatâs Your FavoriteâŚ? ***
33- Beach or Mountains? Or is there another place to like better?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Do you like it when they show and tell you what they want?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
You know that I will be 100% truthful, so ask.
14- Do you have a âDeal Breakerâ, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
12- Whatâs your favorite food? Whatâs your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything⌠Shave meâŚ
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
40~ Whatâs the weirdest place youâve ever had sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŚ
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
67~ Do you like it when your partner moans and/or is vocal during sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
1- What was your first impression of me? Has it changed?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
21~ What was the best date you ever went on? What has been the worst?
62~ Have you used adult toys?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Model/Photographer Police/Criminal
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?
29- How superstitious are you?
14- What's your favorite dessert? Do you a least favorite?
How many partners have you had oral sex with? Who? Care to Share?
65~ Describe the best orgasm youâve ever had? Care to share?
84~ How do you feel about reading/listening to adult stories?
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
Take the short quiz here @ Discover Your Love LanguageÂŽ - The 5 Love LanguagesÂŽ
32- What's your greatest talent? Can I see it right now?
Any that are a turn off?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
What do you dislike about me? I asked you to be 100% honest.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
50~ How many children do you have? What are their ages?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
What was the longest? What was the shortest?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Does the thought excite you? Care to share?
12- What is the weirdest thing you've ever eaten?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
How well do you know me? And some of your thoughts about me
What is your view on sex? Meaning, When/Where/ How often/
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Would you allow me to clean every part of your body with my soapy hands and fingers?
20- Whatâs your favorite candy? Whatâs your least favorite?
19- Whatâs your favorite fairytale? Whatâs your least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
What is your favorite toy? Ever wanted to try a specific toy?
9- Whatâs your favorite season and why? Whatâs your least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
34- Ever been to a concert? What was your favorite? Who would you like to see?
85~ If you gave me a âfree Passâ to have me do anything for one hour, what would you want me to do to you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
3- Should Pluto still be considered a planet? 4- How about smoking?
Would /have you ever given your partner a lap dance and Striptease?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Family Relation Age Play
61~ How willing would you be to try new sexual positions?
Do you watch it? What is your favorite?
Nurse/Patient Celebrity/Fan
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?
4- For a pet, Cat, dog or other?
30~ What's something unexpected that turns you on?
76~ Have you had a threesome? Care to Share?
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?
37- Do you like your name? If you could change it, what would you change it too?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
29~ What are some things that turn you off? What is your biggest turn off?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?