What is the most interesting question you can ask to get to know someone?
10.06.2025 07:38
Nothing too Serious
18- What’s your favorite way to relax after a long day? What’s your least favorite?
4- For a pet, Cat, dog or other?
Which branch of engineering is better: ECE or Civil?
Please share Did you stop?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
A Glucose Monitor for Someone Without Diabetes: Optimal or Overkill? - WSJ
33- Beach or Mountains? Or is there another place to like better?
83~ How do you feel about Porn?
27- What was/ is nickname? Does it have a meaning behind it?
Which is a better option, a love marriage or an arranged marriage in India?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
31- If given a chance to be immortal, would you take it? Why?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
(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…)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
Why do men say women hit the wall at 24?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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?
28- What are some things that people do that irritate you?
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,
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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)
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?
10- What is your favorite family tradition? What’s your least favorite?
38~ Share your most embarrassing sexual memory?
Escort/Client Job Applicant/Hiring Manager
Would you ever want to be woken up with oral and/or intercourse?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
ChatGPT wasn’t built for this, but it’s now the center of my daily routine - Android Authority
The Ice Breaker Questions
36- Do you play video games? What is your favorite? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
What are your controversial and hot takes on Naruto?
Model/Photographer Police/Criminal
3- Should Pluto still be considered a planet? 4- How about smoking?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What is your favorite toy? Ever wanted to try a specific toy?
5~ When you first started having sex, was it what you thought it would be?
19~ Who/when was your first “heartbreak”?
71~ Would you give your partner a hand or foot job? Would you receive one?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
*** Questions about Relationships/Past ***
14- What's your favorite dessert? Do you a least favorite?
52~ What are your hobbies?
9- What’s your favorite season and why? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
15- What bad habit do you wish you could quit? Do you have any addictions?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
15- What's your favorite saying? What word or phrase is your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
9- If you could have three wishes, what would they be? Why?
1- What’s your favorite animal? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Have you ever? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
29- How superstitious are you?
12- What is the weirdest thing you've ever eaten?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
49~ How many times have you been married? Why did they end?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
* Give a rating for each one (0-100)
26~ What side of the bed do you sleep on?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
10~ How many dates are necessary before you to have sex with someone?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
*** Questions About Me ***
If NO, would you ever have one? Would it be with 2 men or 2 women?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
25~ How do you feel about PDA? (Public Display of Affection)
*** What’s Your Favorite…? ***
I would allow you to do it… What would you do to me?
5- Have you ever been hypnotized? Would you allow yourself to be?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
32- What's your greatest talent? Can I see it right now?
82~ Do you have any fantasies involving Role-Playing?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
You know that I will be 100% truthful, so ask.
Master/Slave Boss/Maid
80~ Share your top three fantasies/desires. (Be detailed) 😊
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Do you have a favorite? Is it ok if your partner does?
What was the longest? What was the shortest?
62~ Have you used adult toys?
Do you think this brought you closer together?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
*** Deal Breaker Questions ***
9~ How many times over your lifetime do you think you have had sex so far?
2- What’s your favorite color? Do you a least favorite?
How about if they talk dirty and/or call you names?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
If you say it, I will stop, and we can talk about it when you are ready.
33- If you could visit any time period, when would you pick? Please explain why?
39~ What are your love languages?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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 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?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
40~ What’s the weirdest place you’ve ever had sex?
70~ Would/do you have/like anal sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
11- What's your favorite restaurant? What’s your least favorite?
How many partners have you had oral sex with? Who? Care to Share?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Would you allow me to clean every part of your body with my soapy hands and fingers?
*** Random Questions ***
If YES, was it with 2 men or 2 women? Did you enjoy it?
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- Is there something you’ve always wanted to ask me but you’re afraid?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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?
Does the thought excite you? Care to share?
Teacher/Student Stranger/One Night Stand
52~ Are you willing to make “those types” of bets with your partner?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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?
13- What is the craziest/scariest thing you've ever done?
65~ Describe the best orgasm you’ve ever had? Care to share?
8- What are your thoughts on politics?
What is your view on sex? Meaning, When/Where/ How often/
22~ What is the best pickup line anyone has ever used on you? What was the worst?
7- What are your thoughts on religion? Is there an afterlife?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
18~ Who/when was your first “crush”?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Do you watch it? What is your favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Any that are a turn off?
47~ What would be your dream job and why?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
76~ Have you had a threesome? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Family Relation Age Play
If yes, what?
Would you mind if your partner watched it? How about together vs alone?
19- Do/have you smoked? What do you prefer? How often?
10- List 5 of your top pet peeves.
What is your favorite position? Why?
Would /have you ever given your partner a lap dance and Striptease?
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
6- Do you have dreams? Can you remember them? What do you usually dream about?
29~ What are some things that turn you off? What is your biggest turn off?
17- What’s your favorite holiday? What’s your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
21- What's your favorite way to spend a weekend or time off?
53~ How much can you tell me about the one thing you are most passionate about?
Repairman/Lonely Wife Virgin/Experienced
34~ Do you like the lights on or off during sex?
20- What’s your favorite candy? What’s your least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
That one or two things that made you go hmmmm, OMG or wow!
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
11~ Have you ever been caught by your parents or children or others while having sex?
What do you dislike about me? I asked you to be 100% honest.
Nurse/Patient Celebrity/Fan
3- What Superhero or Superpower would you want to be/have?
13- What’s your favorite drink? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
15~ Have you ever been “in love”? Who? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
51~ What tends to bring a smile to your face?
Doctor/Nurse Stripper/Client
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
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?
61~ How willing would you be to try new sexual positions?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
12- What’s your favorite food? What’s your least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Do you like it when they show and tell you what they want?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
28~ What are some things that turn on? What is your biggest turn on?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
48~ Do you have any siblings? Are you close to your family?
1- What was your first impression of me? Has it changed?
Would you read them together?
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…
8- What's your favorite flavor of ice cream? Do you a least favorite?
How many times do you think you have “made love”?
42~ What’s your biggest regret in life?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
48~ Have you ever paid or been paid for sex?
Would you do it again, and would you rather 2 females or 2 males?
7- What if a person smells a certain way? 8- How about smoking?
19- What’s your favorite fairytale? What’s your least favorite?
50~ How many children do you have? What are their ages?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
84~ How do you feel about reading/listening to adult stories?
If you win, what will you make them do?
How well do you know me? And some of your thoughts about me
36~ What is your favorite time of day to have sex/make love?
How old are you? Male or Female?
What would you say to prove to yourself that it was really you?
81~ Do you have any kinks and/or fetishes?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
45~ How do you feel about me blindfolding you? How about blindfolding me?
23- What is your dream job? What was it as a child?
17- Have you ever done drugs? Which ones? How often?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
44~ Care to share something about yourself that no one else knows about you?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
13- How about having a certain hair cut/style?
Over time has your thoughts on sex changed?
Do you like the “69” position? Do you prefer to be on top or bottom?
Can you Deep Throat? Do you like the taste of yourself?
Any that are a turn off?
21~ What was the best date you ever went on? What has been the worst?
11- List at least 5 things on your bucket list. Have you done any of them already?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
92~ Everyone needs a “safe” word. What is yours?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Get this wrong and this could mean the end… :-) some funny, some not…
89~ Do you like taking showers together?
51~ Are you willing to play adult games with your partner?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
What have you learned about yourself that you did not before this?
7-What do I do in bed that drives you wild? How about, what turns you off?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
37- Do you like your name? If you could change it, what would you change it too?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
67~ Do you like it when your partner moans and/or is vocal during sex?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
30~ What's something unexpected that turns you on?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?