What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 04:40
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How many times do you think you have “made love”?
15~ Have you ever been “in love”? Who? Care to Share?
How much gold is there in the world? - Live Science
38~ Share your most embarrassing sexual memory?
49~ How many times have you been married? Why did they end?
81~ Do you have any kinks and/or fetishes?
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?
20- What’s your favorite candy? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What was the longest? What was the shortest?
Why do people think Mirko is boring in My Hero Academia?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
Why does my mother care about my sister more than me?
11- How about if they like a certain sports team? 12-How about drinking too much?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
This couple paid $19M for 2 Jersey Shore houses. Then they demolished them. - NJ.com
10- What is your favorite family tradition? What’s your least favorite?
Please share Did you stop?
25~ How do you feel about PDA? (Public Display of Affection)
What are some downsides to living in Newfoundland and Labrador (besides the weather)?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Scientists Solve 50-Year Mystery of Strange Zone Deep Inside Earth - SciTechDaily
19~ Who/when was your first “heartbreak”?
7-What do I do in bed that drives you wild? How about, what turns you off?
29- How superstitious are you?
How does it feel to watch your wife get fucked hard?
9- If you could have three wishes, what would they be? Why?
*** Random Questions ***
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What would you say to prove to yourself that it was really you?
47~ What would be your dream job and why?
That one or two things that made you go hmmmm, OMG or wow!
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
1- What was your first impression of me? Has it changed?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
27- What was/ is nickname? Does it have a meaning behind it?
If NO, would you ever have one? Would it be with 2 men or 2 women?
82~ Do you have any fantasies involving Role-Playing?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
2- What’s your favorite color? Do you a least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
17- What’s your favorite holiday? What’s your least favorite?
I would allow you to do it… What would you do to me?
70~ Would/do you have/like anal sex?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Prisoner/Prison Guard Landlord/Tenant
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
36- Do you play video games? What is your favorite? Do you a least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
30~ What's something unexpected that turns you on?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Does the thought excite you? Care to share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
50~ How many children do you have? What are their ages?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Teacher/Student Stranger/One Night Stand
How well do you know me? And some of your thoughts about me
71~ Would you give your partner a hand or foot job? Would you receive one?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
13- What is the craziest/scariest thing you've ever done?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
44~ Care to share something about yourself that no one else knows about you?
How many partners have you had oral sex with? Who? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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,
42~ What’s your biggest regret in life?
22- Do you have any birth marks? How about scars? Care to share how you got them?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
If YES, was it with 2 men or 2 women? Did you enjoy it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
10~ How many dates are necessary before you to have sex with someone?
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?
39~ What are your love languages?
Family Relation Age Play
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
You know that I will be 100% truthful, so ask.
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Do you have a favorite? Is it ok if your partner does?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
48~ Have you ever paid or been paid for sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
4- For a pet, Cat, dog or other?
8- What's your favorite flavor of ice cream? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
The Ice Breaker Questions
83~ How do you feel about Porn?
14- What's your favorite dessert? Do you a least favorite?
48~ Do you have any siblings? Are you close to your family?
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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Model/Photographer Police/Criminal
9- What’s your favorite season and why? What’s your least favorite?
17- Have you ever done drugs? Which ones? How often?
12- What’s your favorite food? What’s your least favorite?
Can you Deep Throat? Do you like the taste of yourself?
Do you like the “69” position? Do you prefer to be on top or bottom?
19- What’s your favorite fairytale? What’s your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What have you learned about me that was new and/or surprising?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
28- What are some things that people do that irritate you?
What is your view on sex? Meaning, When/Where/ How often/
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
14- What is an embarrassing moment in your life? How about your most embarrassing?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
89~ Do you like taking showers together?
51~ Are you willing to play adult games with your partner?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
8- What are your thoughts on politics?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Doctor/Nurse Stripper/Client
32- What's your greatest talent? Can I see it right now?
If you win, what will you make them do?
If yes, what?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
52~ What are your hobbies?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
13- How about having a certain hair cut/style?
How about if they talk dirty and/or call you names?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Nurse/Patient Celebrity/Fan
41~ Are there moments in your past that you would want to change? Please share 3 of them.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
61~ How willing would you be to try new sexual positions?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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…
Do you watch it? What is your favorite?
51~ What tends to bring a smile to your face?
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?
21- What's your favorite way to spend a weekend or time off?
*** What’s Your Favorite…? ***
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
92~ Have you ever had or have an STD? How many? What was it?
5~ When you first started having sex, was it what you thought it would be?
If you say it, I will stop, and we can talk about it when you are ready.
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
52~ Are you willing to make “those types” of bets with your partner?
12- What is the weirdest thing you've ever eaten?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
10- List 5 of your top pet peeves.
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
7- What if a person smells a certain way? 8- How about smoking?
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)
1- What’s your favorite animal? Do you a least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
Would you ever want to be woken up with oral and/or intercourse?
33- Beach or Mountains? Or is there another place to like better?
9~ How many times over your lifetime do you think you have had sex so far?
65~ Describe the best orgasm you’ve ever had? Care to share?
15- What's your favorite saying? What word or phrase is your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
33- If you could visit any time period, when would you pick? Please explain why?
60~ How important is oral sex? Do you like receiving? Do you like giving?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
15- What bad habit do you wish you could quit? Do you have any addictions?
3- What Superhero or Superpower would you want to be/have?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Would you do it again, and would you rather 2 females or 2 males?
3- What’s your favorite smell? Do you a least favorite?
18~ Who/when was your first “crush”?
9- Is there something you’ve always wanted to ask me but you’re afraid?
80~ Share your top three fantasies/desires. (Be detailed) 😊
18- What’s your favorite way to relax after a long day? What’s your least favorite?
34~ Do you like the lights on or off during sex?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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…
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Have you ever? Care to Share?
How old are you? Male or Female?
Any that are a turn off?
11- What's your favorite restaurant? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
13- What’s your favorite drink? What’s your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
23- What is your dream job? What was it as a child?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you think this brought you closer together?
What do you dislike about me? I asked you to be 100% honest.
76~ Have you had a threesome? Care to Share?
*** Questions About Me ***
20- Do you have any tattoos? 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?
Would you allow me to clean every part of your body with my soapy hands and fingers?
22- What is your favorite childhood memory? What is your least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
62~ Have you used adult toys?
11~ Have you ever been caught by your parents or children or others while having sex?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
31- If given a chance to be immortal, would you take it? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
40~ What’s the weirdest place you’ve ever had sex?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
21~ What was the best date you ever went on? What has been the worst?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
*** Deal Breaker Questions ***
19- Do/have you smoked? What do you prefer? How often?
What have you learned about yourself that you did not before this?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
28~ What are some things that turn on? What is your biggest turn on?
1~ How old were you when you had your first kiss? Who? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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?
*** Questions about Relationships/Past ***
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Over time has your thoughts on sex changed?
36~ What is your favorite time of day to have sex/make love?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Would you mind if your partner watched it? How about together vs alone?
What is your favorite toy? Ever wanted to try a specific toy?
84~ How do you feel about reading/listening to adult stories?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Would you read them together?
Any that are a turn off?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
92~ Everyone needs a “safe” word. What is yours?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
* Give a rating for each one (0-100)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
13~ Is there a difference between, making love, having sex, and fucking?
26~ What side of the bed do you sleep on?
What is your favorite position? Why?
Master/Slave Boss/Maid
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
(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…)
Escort/Client Job Applicant/Hiring Manager
Nothing too Serious