What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 00:21
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)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Is it just me, or do we all hate Sasuke from Naruto?
51~ Are you willing to play adult games with your partner?
8- What are your thoughts on politics?
38~ Share your most embarrassing sexual memory?
What is your most erotic sex story?
7- What if a person smells a certain way? 8- How about smoking?
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
Is the Philippines PH a poor 3rd world or 4th world country forever and forever?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Do you like the “69” position? Do you prefer to be on top or bottom?
33- Beach or Mountains? Or is there another place to like better?
Defense Department signs OpenAI for $200 million 'frontier AI' pilot project - theregister.com
42~ What’s your biggest regret in life?
How about if they talk dirty and/or call you names?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
The Ice Breaker Questions
How many partners have you had oral sex with? Who? Care to Share?
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…
11- How about if they like a certain sports team? 12-How about drinking too much?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
15- What's your favorite saying? What word or phrase is your least favorite?
What type of narcissist cheats more and gets pleasure out of hurting you, even if they're married?
83~ How do you feel about Porn?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
Will you share your wife? Can she take both of us at the same time?
What have you learned about me that was new and/or surprising?
10~ How many dates are necessary before you to have sex with someone?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Does the Lil Wayne song ‘Lollipop’ refers to a Lollipop sweet or a metaphor?
39~ What are your love languages?
10- List 5 of your top pet peeves.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Why do so many 18 to 29-year-old men struggle in dating?
29~ What are some things that turn you off? What is your biggest turn off?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
49~ How many times have you been married? Why did they end?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
1~ How old were you when you had your first kiss? Who? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
34- Ever been to a concert? What was your favorite? Who would you like to see?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
9- Is there something you’ve always wanted to ask me but you’re afraid?
13- How about having a certain hair cut/style?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
3- What’s your favorite smell? Do you a least favorite?
28- What are some things that people do that irritate you?
Would /have you ever given your partner a lap dance and Striptease?
Do you think this brought you closer together?
92~ Everyone needs a “safe” word. What is yours?
52~ Are you willing to make “those types” of bets with your partner?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Repairman/Lonely Wife Virgin/Experienced
8- What's your favorite flavor of ice cream? Do you a least favorite?
70~ Would/do you have/like anal sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
21- What's your favorite way to spend a weekend or time off?
What have you learned about yourself that you did not before this?
62~ Have you used adult toys?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
27- What was/ is nickname? Does it have a meaning behind it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What do you dislike about me? I asked you to be 100% honest.
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
19- Do/have you smoked? What do you prefer? How often?
What is your favorite toy? Ever wanted to try a specific toy?
9- If you could have three wishes, what would they be? Why?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
4- For a pet, Cat, dog or other?
Model/Photographer Police/Criminal
Prisoner/Prison Guard Landlord/Tenant
45~ How do you feel about me blindfolding you? How about blindfolding me?
(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…)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Please share Did you stop?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
12- What’s your favorite food? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
13- What is the craziest/scariest thing you've ever done?
28~ What are some things that turn on? What is your biggest turn on?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
11- List at least 5 things on your bucket list. Have you done any of them already?
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?
Nothing too Serious
29- How superstitious are you?
76~ Have you had a threesome? Care to Share?
52~ What are your hobbies?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Have you ever? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Over time has your thoughts on sex changed?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
48~ Do you have any siblings? Are you close to your family?
80~ Share your top three fantasies/desires. (Be detailed) 😊
14- What's your favorite dessert? Do you a least favorite?
1- What was your first impression of me? Has it changed?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
13- What’s your favorite drink? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Any that are a turn off?
67~ Do you like it when your partner moans and/or is vocal during sex?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
*** Deal Breaker Questions ***
* Give a rating for each one (0-100)
Can you Deep Throat? Do you like the taste of yourself?
6- Do you have dreams? Can you remember them? What do you usually dream about?
*** What’s Your Favorite…? ***
22~ What is the best pickup line anyone has ever used on you? What was the worst?
81~ Do you have any kinks and/or fetishes?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
31- If given a chance to be immortal, would you take it? Why?
36- Do you play video games? What is your favorite? Do you a least favorite?
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
13~ Is there a difference between, making love, having sex, and fucking?
Teacher/Student Stranger/One Night Stand
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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,
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
18- How often do you drink alcohol? What is your favorite drink?
7- What are your thoughts on religion? Is there an afterlife?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
23- What is your dream job? What was it as a child?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
19~ Who/when was your first “heartbreak”?
11~ Have you ever been caught by your parents or children or others while having sex?
19- What’s your favorite fairytale? What’s your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
53~ How much can you tell me about the one thing you are most passionate about?
If you win, what will you make them do?
10- What is your favorite family tradition? What’s your least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Would you mind if your partner watched it? How about together vs alone?
Doctor/Nurse Stripper/Client
Nurse/Patient Celebrity/Fan
26~ What side of the bed do you sleep on?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
12- What is the weirdest thing you've ever eaten?
How well do you know me? And some of your thoughts about me
Do you have a favorite? Is it ok if your partner does?
What was the longest? What was the shortest?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Get this wrong and this could mean the end… :-) some funny, some not…
That one or two things that made you go hmmmm, OMG or wow!
44~ Care to share something about yourself that no one else knows about you?
89~ Do you like taking showers together?
22- Do you have any birth marks? How about scars? Care to share how you got them?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
51~ What tends to bring a smile to your face?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
32- What's your greatest talent? Can I see it right now?
Would you read them together?
92~ Have you ever had or have an STD? How many? What was it?
22- What is your favorite childhood memory? What is your least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
34~ Do you like the lights on or off during sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
If yes, what?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
3- What Superhero or Superpower would you want to be/have?
*** Questions about Relationships/Past ***
What is your view on sex? Meaning, When/Where/ How often/
18~ Who/when was your first “crush”?
Master/Slave Boss/Maid
9- What’s your favorite season and why? What’s your least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you like it when they show and tell you what they want?
25~ How do you feel about PDA? (Public Display of Affection)
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
61~ How willing would you be to try new sexual positions?
If you say it, I will stop, and we can talk about it when you are ready.
You know that I will be 100% truthful, so ask.
2- What’s your favorite color? Do you a least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
33- If you could visit any time period, when would you pick? Please explain why?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
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/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
What is your favorite position? Why?
How many times do you think you have “made love”?
43~ Ever had your hair pulled 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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Do you watch it? What is your favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
48~ Have you ever paid or been paid for sex?
1- What’s your favorite animal? Do you a least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
Escort/Client Job Applicant/Hiring Manager
40~ What’s the weirdest place you’ve ever had sex?
56~ Would you ever go to a strip club 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?
Any that are a turn off?
How old are you? Male or Female?
15~ Have you ever been “in love”? Who? 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…
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
21~ What was the best date you ever went on? What has been the worst?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
71~ Would you give your partner a hand or foot job? Would you receive one?
9~ How many times over your lifetime do you think you have had sex so far?
*** Questions About Me ***
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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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)
7-What do I do in bed that drives you wild? How about, what turns you off?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Would you ever want to be woken up with oral and/or intercourse?
Will you cheat again? How can, you be sure? Define what cheating is to you.
47~ What would be your dream job and why?
What would you say to prove to yourself that it was really you?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
30~ What's something unexpected that turns you on?
*** Random Questions ***
Family Relation Age Play
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
50~ How many children do you have? What are their ages?
14- What is an embarrassing moment in your life? How about your most embarrassing?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
36~ What is your favorite time of day to have sex/make love?
Does the thought excite you? Care to share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
65~ Describe the best orgasm you’ve ever had? Care to share?
17- What’s your favorite holiday? What’s your least favorite?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
17- Have you ever done drugs? Which ones? How often?
Would you do it again, and would you rather 2 females or 2 males?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
I would allow you to do it… What would you do to me?