What is the most interesting question you can ask to get to know someone?
Last Updated: 03.07.2025 01:24
What have you learned about yourself that you did not before this?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
11- What's your favorite restaurant? What’s your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
71~ Would you give your partner a hand or foot job? Would you receive one?
Woodruff departs rehab outing after taking liner to elbow - MLB.com
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
That one or two things that made you go hmmmm, OMG or wow!
Need a different reason to eat more fiber? How about microplastics? - The Seattle Times
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,
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
'Housewives' Exec Assistant and Mom of 2 Dies 'Moments After Giving Birth' to Son - TODAY.com
22~ What is the best pickup line anyone has ever used on you? What was the worst?
9- What’s your favorite season and why? What’s your least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
Jake Paul captures unanimous decision victory over Julio Cesar Chavez - New York Post
Any that are a turn off?
Do you have a favorite? Is it ok if your partner does?
How about if they talk dirty and/or call you names?
Stress hormones: Why quick fixes won't lower our cortisol levels - BBC
81~ Do you have any kinks and/or fetishes?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
I would allow you to do it… What would you do to me?
New study maps psychological pathway from childhood abuse to adolescent addiction - PsyPost
51~ Are you willing to play adult games with your partner?
12- What’s your favorite food? What’s your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Pablo Lopez To Miss Multiple Months With Teres Major Strain - MLB Trade Rumors
Escort/Client Job Applicant/Hiring Manager
8- What are your thoughts on politics?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Hinge CEO Justin McLeod says dating AI chatbots is ‘playing with fire’ - The Verge
Please share Did you stop?
You know that I will be 100% truthful, so ask.
11- How about if they like a certain sports team? 12-How about drinking too much?
What are the best items to buy from a furniture shop?
Doctor/Nurse Stripper/Client
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would you read them together?
When writing a novel, how can a character be developed well, but QUICKLY?
34~ Do you like the lights on or off during sex?
Any that are a turn off?
*** Random Questions ***
89~ Do you like taking showers together?
67~ Do you like it when your partner moans and/or is vocal during sex?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
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How well do you know me? And some of your thoughts about me
What would you say to prove to yourself that it was really you?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Asperiores culpa provident similique ab.
17- What’s your favorite holiday? What’s your least favorite?
14- What's your favorite dessert? Do you a least favorite?
How old are you? Male or Female?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
62~ Have you used adult toys?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
21~ What was the best date you ever went on? What has been the worst?
23- What is your dream job? What was it as a child?
1~ How old were you when you had your first kiss? Who? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
29- How superstitious are you?
Have you ever? Care to Share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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?
Do you think this brought you closer together?
3- Should Pluto still be considered a planet? 4- How about smoking?
92~ Have you ever had or have an STD? How many? What was it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
* Give a rating for each one (0-100)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
19- Do/have you smoked? What do you prefer? How often?
15- What bad habit do you wish you could quit? Do you have any addictions?
*** Questions About Me ***
5- Have you ever been hypnotized? Would you allow yourself to be?
17- Have you ever done drugs? Which ones? How often?
Repairman/Lonely Wife Virgin/Experienced
9- If you could have three wishes, what would they be? Why?
83~ How do you feel about Porn?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
20- What’s your favorite candy? What’s your least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
The Ice Breaker Questions
Would you do it again, and would you rather 2 females or 2 males?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Do you watch it? What is your favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Would you allow me to clean every part of your body with my soapy hands and fingers?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
* 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…
Does the thought excite you? Care to share?
3- What’s your favorite smell? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
15- What's your favorite saying? What word or phrase is your least favorite?
How many partners have you had oral sex with? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
12- What is the weirdest thing you've ever eaten?
*** Questions about Relationships/Past ***
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
36- Do you play video games? What is your favorite? Do you a 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?
53~ How much can you tell me about the one thing you are most passionate about?
Would you mind if your partner watched it? How about together vs alone?
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?
Over time has your thoughts on sex changed?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Can you Deep Throat? Do you like the taste of yourself?
*** Deal Breaker Questions ***
47~ What would be your dream job and why?
Do you like it when they show and tell you what they want?
25~ How do you feel about PDA? (Public Display of Affection)
8- What's your favorite flavor of ice cream? 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.
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
13- What’s your favorite drink? What’s your least favorite?
Family Relation Age Play
13- What is the craziest/scariest thing you've ever done?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
If yes, what?
Prisoner/Prison Guard Landlord/Tenant
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
19~ Who/when was your first “heartbreak”?
61~ How willing would you be to try new sexual positions?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
If you win, what will you make them do?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
1- What was your first impression of me? Has it changed?
33- Beach or Mountains? Or is there another place to like better?
49~ How many times have you been married? Why did they end?
37- Do you like your name? If you could change it, what would you change it too?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
38~ Share your most embarrassing sexual memory?
21- What's your favorite way to spend a weekend or time off?
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
18~ Who/when was your first “crush”?
22- Do you have any birth marks? How about scars? Care to share how you got them?
6- Do you have dreams? Can you remember them? What do you usually dream about?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
7-What do I do in bed that drives you wild? How about, what turns you off?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
36~ What is your favorite time of day to have sex/make love?
9~ How many times over your lifetime do you think you have had sex so far?
15~ Have you ever been “in love”? Who? Care to Share?
Model/Photographer Police/Criminal
26~ What side of the bed do you sleep on?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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…
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
32- What's your greatest talent? Can I see it right now?
44~ Care to share something about yourself that no one else knows about you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Get this wrong and this could mean the end… :-) some funny, some not…
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
92~ Everyone needs a “safe” word. What is yours?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
What have you learned about me that was new and/or surprising?
10- What is your favorite family tradition? What’s your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
31- If given a chance to be immortal, would you take it? Why?
Do you like the “69” position? Do you prefer to be on top or bottom?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
What was the longest? What was the shortest?
14- What is an embarrassing moment in your life? How about your most embarrassing?
3- What Superhero or Superpower would you want to be/have?
4- For a pet, Cat, dog or other?
27- What was/ is nickname? Does it have a meaning behind it?
51~ What tends to bring a smile to your face?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
13~ Is there a difference between, making love, having sex, and fucking?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Would /have you ever given your partner a lap dance and Striptease?
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)
11~ Have you ever been caught by your parents or children or others while having sex?
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?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Nothing too Serious
3- What was the most surprising thing you’ve learned about me throughout our relationship?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
What is your favorite position? Why?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
What is your view on sex? Meaning, When/Where/ How often/
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
10- List 5 of your top pet peeves.
13- How about having a certain hair cut/style?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
45~ How do you feel about me blindfolding you? How about blindfolding me?
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?
48~ Do you have any siblings? Are you close to your family?
2- What’s your favorite color? Do you a least favorite?
52~ What are your hobbies?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
If NO, would you ever have one? Would it be with 2 men or 2 women?
5~ When you first started having sex, was it what you thought it would be?
69~ Are you willing to have sex while you or your partner is on their period? How about oral 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?
Would you ever want to be woken up with oral and/or intercourse?
65~ Describe the best orgasm you’ve ever had? Care to share?
How many times do you think you have “made love”?
82~ Do you have any fantasies involving Role-Playing?
9- Is there something you’ve always wanted to ask me but you’re afraid?
*** What’s Your Favorite…? ***
40~ What’s the weirdest place you’ve ever had sex?
48~ Have you ever paid or been paid for sex?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
29~ What are some things that turn you off? What is your biggest turn off?
80~ Share your top three fantasies/desires. (Be detailed) 😊
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
28- What are some things that people do that irritate you?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
76~ Have you had a threesome? Care to Share?
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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
18- How often do you drink alcohol? What is your favorite drink?
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?
What do you dislike about me? I asked you to be 100% honest.
39~ What are your love languages?
(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…)
Nurse/Patient Celebrity/Fan
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
30~ What's something unexpected that turns you on?
10~ How many dates are necessary before you to have sex with someone?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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’s the longest time you gone without having sex, after, having it? How much time between the others?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
42~ What’s your biggest regret in life?
If YES, was it with 2 men or 2 women? Did you enjoy it?
11- List at least 5 things on your bucket list. Have you done any of them already?
If you say it, I will stop, and we can talk about it when you are ready.
7- What if a person smells a certain way? 8- How about smoking?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Master/Slave Boss/Maid
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
84~ How do you feel about reading/listening to adult stories?
34- Ever been to a concert? What was your favorite? Who would you like to see?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
50~ How many children do you have? What are their ages?
Teacher/Student Stranger/One Night Stand