What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 11:47
26~ What side of the bed do you sleep on?
32- What's your greatest talent? Can I see it right now?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
How can I fall asleep fast at night?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Any that are a turn off?
21~ What was the best date you ever went on? What has been the worst?
25~ How do you feel about PDA? (Public Display of Affection)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
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?
If there exists a “New York of Australia”, is it Sydney or Melbourne?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What have you learned about yourself that you did not before this?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
22- Do you have any birth marks? How about scars? Care to share how you got them?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Does a person with schizophrenia hear voices?
61~ How willing would you be to try new sexual positions?
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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
9- What’s your favorite season and why? What’s your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How was cancer treatment different in the US and the UK?
5- Have you ever been hypnotized? Would you allow yourself to be?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
23- What is your dream job? What was it as a child?
Were any US Generals hurt or killed yesterday in Damascus, Syria, yesterday 5/9/24?
20- What’s your favorite candy? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
3- What’s your favorite smell? Do you a least favorite?
What can you do if you are a full-grown adult, but never experienced being a child?
13- What’s your favorite drink? What’s your least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Why do so many 18 to 29-year-old men struggle in dating?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Get this wrong and this could mean the end… :-) some funny, some not…
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 do you think of the Quora group "It's Ok to Be White" for people who are proud of being white?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
92~ Everyone needs a “safe” word. What is yours?
33- If you could visit any time period, when would you pick? Please explain why?
Prisoner/Prison Guard Landlord/Tenant
13- What is the craziest/scariest thing you've ever done?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
53~ How much can you tell me about the one thing you are most passionate about?
48~ Have you ever paid or been paid for sex?
13~ Is there a difference between, making love, having sex, and fucking?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
1- What was your first impression of me? Has it changed?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
38~ Share your most embarrassing sexual memory?
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)
Will you cheat again? How can, you be sure? Define what cheating is to you.
6- What’s your favorite TV series? Do you have a favorite genre? 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.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
1~ How old were you when you had your first kiss? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
4- For a pet, Cat, dog or other?
What is your view on sex? Meaning, When/Where/ How often/
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?
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?
52~ Are you willing to make “those types” of bets with your partner?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
49~ How many times have you been married? Why did they end?
*** Questions about Relationships/Past ***
What is your favorite position? Why?
28~ What are some things that turn on? What is your biggest turn on?
Repairman/Lonely Wife Virgin/Experienced
The Ice Breaker Questions
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
31- If given a chance to be immortal, would you take it? Why?
36~ What is your favorite time of day to have sex/make love?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Family Relation Age Play
How many partners have you had oral sex with? Who? Care to Share?
12- What’s your favorite food? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
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,
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
10- What is your favorite family tradition? What’s your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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…
22- What is your favorite childhood memory? What is your least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
*** Questions About Me ***
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
If yes, what?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Master/Slave Boss/Maid
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
71~ Would you give your partner a hand or foot job? Would you receive one?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
82~ Do you have any fantasies involving Role-Playing?
37- Do you like your name? If you could change it, what would you change it too?
29~ What are some things that turn you off? What is your biggest turn off?
76~ Have you had a threesome? Care to Share?
84~ How do you feel about reading/listening to adult stories?
8- What are your thoughts on politics?
Can you Deep Throat? Do you like the taste of yourself?
If you win, what will you make them do?
Doctor/Nurse Stripper/Client
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?
33- Beach or Mountains? Or is there another place to like better?
Would /have you ever given your partner a lap dance and Striptease?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
40~ What’s the weirdest place you’ve ever had sex?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Do you think this brought you closer together?
29- How superstitious are you?
65~ Describe the best orgasm you’ve ever had? Care to share?
28- What are some things that people do that irritate you?
52~ What are your hobbies?
15~ Have you ever been “in love”? Who? Care to Share?
How old are you? Male or Female?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
48~ Do you have any siblings? Are you close to your family?
Nothing too Serious
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
7- What if a person smells a certain way? 8- How about smoking?
9- If you could have three wishes, what would they be? Why?
19- Do/have you smoked? What do you prefer? How often?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
51~ Are you willing to play adult games with your partner?
83~ How do you feel about Porn?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Nurse/Patient Celebrity/Fan
12- What is the weirdest thing you've ever eaten?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
18~ Who/when was your first “crush”?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
34~ Do you like the lights on or off during sex?
How many times do you think you have “made love”?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
19~ Who/when was your first “heartbreak”?
51~ What tends to bring a smile to your face?
30~ What's something unexpected that turns you on?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
What have you learned about me that was new and/or surprising?
6- Do you have dreams? Can you remember them? What do you usually dream about?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Over time has your thoughts on sex changed?
92~ Have you ever had or have an STD? How many? What was it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
47~ What would be your dream job and why?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
42~ What’s your biggest regret in life?
*** Random Questions ***
Does the thought excite you? Care to share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
9~ How many times over your lifetime do you think you have had sex so far?
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?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
15- What's your favorite saying? What word or phrase is your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
*** What’s Your Favorite…? ***
(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…)
Please share Did you stop?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What would you say to prove to yourself that it was really you?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
Have you ever? Care to Share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
11- List at least 5 things on your bucket list. Have you done any of them already?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Model/Photographer Police/Criminal
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
8- What's your favorite flavor of ice cream? Do you a least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
50~ How many children do you have? What are their ages?
17- What’s your favorite holiday? What’s your least favorite?
17- Have you ever done drugs? Which ones? How often?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
2- What’s your favorite color? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
*** Deal Breaker Questions ***
14- What's your favorite dessert? Do you a least favorite?
10- List 5 of your top pet peeves.
81~ Do you have any kinks and/or fetishes?
Any that are a turn off?
14- What is an embarrassing moment in your life? How about your most embarrassing?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
How well do you know me? And some of your thoughts about me
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
13- How about having a certain hair cut/style?
Would you do it again, and would you rather 2 females or 2 males?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
What was the longest? What was the shortest?
44~ Care to share something about yourself that no one else knows about you?
Would you mind if your partner watched it? How about together vs alone?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
5~ When you first started having sex, was it what you thought it would be?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
You know that I will be 100% truthful, so ask.
11- What's your favorite restaurant? What’s your least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
11- How about if they like a certain sports team? 12-How about drinking too much?
3- Should Pluto still be considered a planet? 4- How about smoking?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
3- What Superhero or Superpower would you want to be/have?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
If NO, would you ever have one? Would it be with 2 men or 2 women?
62~ Have you used adult toys?
1- What’s your favorite animal? Do you a least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
I would allow you to do it… What would you do to me?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
How about if they talk dirty and/or call you names?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Do you have a favorite? Is it ok if your partner does?
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…
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
19- What’s your favorite fairytale? What’s your least favorite?
Escort/Client Job Applicant/Hiring Manager
Would you read them together?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would you allow me to clean every part of your body with my soapy hands and fingers?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
18- How often do you drink alcohol? What is your favorite drink?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
70~ Would/do you have/like anal sex?
89~ Do you like taking showers together?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What do you dislike about me? I asked you to be 100% honest.
Do you watch it? What is your favorite?