What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 03:50
What have you learned about me that was new and/or surprising?
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?
Any that are a turn off?
How do I get my body in shape?
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Prince William’s friend Sunjay Kapur dies after swallowing a bee at polo match - New York Daily News
That one or two things that made you go hmmmm, OMG or wow!
Do you like it when they show and tell you what they want?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
22- Do you have any birth marks? How about scars? Care to share how you got them?
11- What's your favorite restaurant? What’s your 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?
48~ Do you have any siblings? Are you close to your family?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
61~ How willing would you be to try new sexual positions?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
1- What was your first impression of me? Has it changed?
13~ Is there a difference between, making love, having sex, and fucking?
53~ How much can you tell me about the one thing you are most passionate about?
50~ How many children do you have? What are their ages?
What does the stink of the skunk look like? Why would it be dangerous?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Report: New Development in Trey Hendrickson Contract Situation - Sports Illustrated
Over time has your thoughts on sex changed?
Do you watch it? What is your favorite?
Have you ever? Care to Share?
Why is China the first in the world to counter the "reciprocal tariff"?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Is helping Ukraine worth risking WW3?
47~ What would be your dream job and why?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What is the cost of living in Sweden as a family?
28~ What are some things that turn on? What is your biggest turn on?
13- How about having a certain hair cut/style?
42~ What’s your biggest regret in life?
*** Questions About Me ***
32- What's your greatest talent? Can I see it right now?
28- What are some things that people do that irritate you?
Does the thought excite you? Care to share?
13- What is the craziest/scariest thing you've ever done?
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?
9~ How many times over your lifetime do you think you have had sex so far?
51~ Are you willing to play adult games with your partner?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
12- What’s your favorite food? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Repairman/Lonely Wife Virgin/Experienced
19~ Who/when was your first “heartbreak”?
Teacher/Student Stranger/One Night Stand
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
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…
52~ Are you willing to make “those types” of bets with your partner?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
*** Questions about Relationships/Past ***
14- What is an embarrassing moment in your life? How about your most embarrassing?
36~ What is your favorite time of day to have sex/make love?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
70~ Would/do you have/like anal sex?
You know that I will be 100% truthful, so ask.
14- What's your favorite dessert? Do you a least favorite?
18- How often do you drink alcohol? What is your favorite drink?
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)
35- Do you like playing board or cards game? 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?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
9- What’s your favorite season and why? What’s your least favorite?
*** Random Questions ***
Would you do it again, and would you rather 2 females or 2 males?
89~ Do you like taking showers together?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
If yes, what?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Can you Deep Throat? Do you like the taste of yourself?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Do you think this brought you closer together?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
67~ Do you like it when your partner moans and/or is vocal during sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
What is your favorite position? Why?
10- What is your favorite family tradition? What’s your least favorite?
Master/Slave Boss/Maid
7- What are your thoughts on religion? Is there an afterlife?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
29- How superstitious are you?
26~ What side of the bed do you sleep on?
How old are you? Male or Female?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
20- What’s your favorite candy? What’s your least favorite?
*** What’s Your Favorite…? ***
Do you like the “69” position? Do you prefer to be on top or bottom?
8- What are your thoughts on politics?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
5~ When you first started having sex, was it what you thought it would be?
Would you mind if your partner watched it? How about together vs alone?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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?
82~ Do you have any fantasies involving Role-Playing?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Escort/Client Job Applicant/Hiring Manager
What do you dislike about me? I asked you to be 100% honest.
48~ Have you ever paid or been paid for sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
How about if they talk dirty and/or call you names?
What have you learned about yourself that you did not before this?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
8- What's your favorite flavor of ice cream? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
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?
17- Have you ever done drugs? Which ones? How often?
65~ Describe the best orgasm you’ve ever had? Care to share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
92~ Have you ever had or have an STD? How many? What was it?
What would you say to prove to yourself that it was really you?
1~ How old were you when you had your first kiss? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
36- Do you play video games? What is your favorite? Do you a least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
33- If you could visit any time period, when would you pick? Please explain why?
7- What if a person smells a certain way? 8- How about smoking?
Nothing too Serious
39~ What are your love languages?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
How many times do you think you have “made love”?
49~ How many times have you been married? Why did they end?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
2- What’s your favorite color? Do you a least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
17- What’s your favorite holiday? What’s your least favorite?
* Give a rating for each one (0-100)
34~ Do you like the lights on or off during sex?
30~ What's something unexpected that turns you on?
15- What's your favorite saying? What word or phrase is your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
81~ Do you have any kinks and/or fetishes?
19- Do/have you smoked? What do you prefer? How often?
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,
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
44~ Care to share something about yourself that no one else knows about you?
Get this wrong and this could mean the end… :-) some funny, some not…
If you win, what will you make them do?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
23- What is your dream job? What was it as a child?
What is your view on sex? Meaning, When/Where/ How often/
11- List at least 5 things on your bucket list. Have you done any of them already?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
3- What Superhero or Superpower would you want to be/have?
3- What’s your favorite smell? Do you a least favorite?
Nurse/Patient Celebrity/Fan
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?
If you say it, I will stop, and we can talk about it when you are ready.
Do you have a favorite? Is it ok if your partner does?
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?
31- If given a chance to be immortal, would you take it? Why?
11~ Have you ever been caught by your parents or children or others while having sex?
15~ Have you ever been “in love”? Who? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
19- What’s your favorite fairytale? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
10- List 5 of your top pet peeves.
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Any that are a turn off?
18~ Who/when was your first “crush”?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
92~ Everyone needs a “safe” word. What is yours?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
84~ How do you feel about reading/listening to adult stories?
What was the longest? What was the shortest?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
80~ Share your top three fantasies/desires. (Be detailed) 😊
How many partners have you had oral sex with? Who? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
60~ How important is oral sex? Do you like receiving? Do you like giving?
I would allow you to do it… What would you do to me?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
The Ice Breaker Questions
38~ Share your most embarrassing sexual memory?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
71~ Would you give your partner a hand or foot job? Would you receive one?
62~ Have you used adult toys?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
37- Do you like your name? If you could change it, what would you change it too?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
13- What’s your favorite drink? What’s your least favorite?
52~ What are your hobbies?
1- What’s your favorite animal? Do you a least favorite?
4- For a pet, Cat, dog or other?
5- Have you ever been hypnotized? Would you allow yourself to be?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
(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
How well do you know me? And some of your thoughts about me
22- What is your favorite childhood memory? What is your least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
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…
40~ What’s the weirdest place you’ve ever had sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
45~ How do you feel about me blindfolding you? How about blindfolding me?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Please share Did you stop?
What is your favorite toy? Ever wanted to try a specific toy?
Would you read them together?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
33- Beach or Mountains? Or is there another place to like better?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
15- What bad habit do you wish you could quit? Do you have any addictions?
*** Deal Breaker Questions ***
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
21~ What was the best date you ever went on? What has been the worst?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
10~ How many dates are necessary before you to have sex with someone?
Doctor/Nurse Stripper/Client
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 NO, would you ever have one? Would it be with 2 men or 2 women?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Would you ever want to be woken up with oral and/or intercourse?
83~ How do you feel about Porn?
Family Relation Age Play
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
9- If you could have three wishes, what would they be? Why?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
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?
51~ What tends to bring a smile to your face?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
12- What is the weirdest thing you've ever eaten?