What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 08:17
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
67~ Do you like it when your partner moans and/or is vocal during sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Why do old men think young women and girls would want them over guys their own age?
Would you ever want to be woken up with oral and/or intercourse?
51~ Are you willing to play adult games with your partner?
13~ Is there a difference between, making love, having sex, and fucking?
New iOS 26 design makes me want an iPhone 17 Air more than ever - 9to5Mac
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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?
Would /have you ever given your partner a lap dance and Striptease?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
13- What is the craziest/scariest thing you've ever done?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
60 years ago, Ed White went out for walk photo of the day for June 3, 2025 - Space
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
62~ Have you used adult toys?
What are some ways to cope with paranoid thoughts about being gangstalked or targeted individuals?
13- How about having a certain hair cut/style?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
15- What's your favorite saying? What word or phrase is your least favorite?
What are the new technological advancements we should adopt?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What actor is genetically gifted?
Would you do it again, and would you rather 2 females or 2 males?
29~ What are some things that turn you off? What is your biggest turn off?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What are some good sunscreens for a teen with oily skin?
1- What was your first impression of me? Has it changed?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Is 1500 calories enough for a 5’3 15-year-old who is non-active?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
12- What is the weirdest thing you've ever eaten?
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)
Newspaper headlines: Spending Review 'renewing Britain' or 'reckless splurge' - BBC
46~ Have you ever used furniture, or other types of things to aid you while having sex?
31- If given a chance to be immortal, would you take it? Why?
* Give a rating for each one (0-100)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Boy, 8, dies hours after complaining of headache when infection spread to brain - The US Sun
If you win, what will you make them do?
52~ What are your hobbies?
Any that are a turn off?
26~ What side of the bed do you sleep on?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Homophobia is clearly a harmful mental sickness. What can LGBT people do to cure it?
44~ Care to share something about yourself that no one else knows about you?
11- List at least 5 things on your bucket list. Have you done any of them already?
2- What’s your favorite color? Do you a least favorite?
Did sharing a wife turn out okay?
49~ How many times have you been married? Why did they end?
Prisoner/Prison Guard Landlord/Tenant
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
51~ What tends to bring a smile to your face?
50~ How many children do you have? What are their ages?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
21~ What was the best date you ever went on? What has been the worst?
83~ How do you feel about Porn?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Do you watch it? What is your favorite?
70~ Would/do you have/like anal sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
65~ Describe the best orgasm you’ve ever had? Care to share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What is your favorite position? Why?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Any that are a turn off?
19- What’s your favorite fairytale? What’s your least favorite?
Would you mind if your partner watched it? How about together vs alone?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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…
How about if they talk dirty and/or call you names?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
7- What are your thoughts on religion? Is there an afterlife?
Do you like it when they show and tell you what they want?
10- List 5 of your top pet peeves.
23- What is your dream job? What was it as a child?
7-What do I do in bed that drives you wild? How about, what turns you off?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
80~ Share your top three fantasies/desires. (Be detailed) 😊
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
How many partners have you had oral sex with? Who? Care to Share?
48~ Have you ever paid or been paid for sex?
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?
What was the longest? What was the shortest?
*** Questions about Relationships/Past ***
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
11~ Have you ever been caught by your parents or children or others while having sex?
What would you say to prove to yourself that it was really you?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
What have you learned about me that was new and/or surprising?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
17- What’s your favorite holiday? What’s your least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
If you say it, I will stop, and we can talk about it when you are ready.
Escort/Client Job Applicant/Hiring Manager
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
71~ Would you give your partner a hand or foot job? Would you receive one?
14- What's your favorite dessert? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
9~ How many times over your lifetime do you think you have had sex so far?
18~ Who/when was your first “crush”?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
*** Deal Breaker Questions ***
9- If you could have three wishes, what would they be? Why?
9- What’s your favorite season and why? What’s your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
30~ What's something unexpected that turns you on?
Can you Deep Throat? Do you like the taste of yourself?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
3- What Superhero or Superpower would you want to be/have?
53~ How much can you tell me about the one thing you are most passionate about?
Repairman/Lonely Wife Virgin/Experienced
3- Should Pluto still be considered a planet? 4- How about smoking?
76~ Have you had a threesome? Care to Share?
*** What’s Your Favorite…? ***
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
32- What's your greatest talent? Can I see it right now?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
37- Do you like your name? If you could change it, what would you change it too?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Master/Slave Boss/Maid
1~ How old were you when you had your first kiss? Who? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
33- Beach or Mountains? Or is there another place to like better?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Please share Did you stop?
29- How superstitious are you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
What do you dislike about me? I asked you to be 100% honest.
22- Do you have any birth marks? How about scars? Care to share how you got them?
How well do you know me? And some of your thoughts about me
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
If yes, what?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
19~ Who/when was your first “heartbreak”?
15- What bad habit do you wish you could quit? Do you have any addictions?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Have you ever? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
42~ What’s your biggest regret in life?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
22- What is your favorite childhood memory? What is your least favorite?
8- What are your thoughts on politics?
82~ Do you have any fantasies involving Role-Playing?
12- What’s your favorite food? What’s your least favorite?
The Ice Breaker Questions
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Nurse/Patient Celebrity/Fan
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
How many times do you think you have “made love”?
28- What are some things that people do that irritate you?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
(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…)
36~ What is your favorite time of day to have sex/make love?
4- For a pet, Cat, dog or other?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
1- What’s your favorite animal? Do you a least favorite?
19- Do/have you smoked? What do you prefer? How often?
Do you have a favorite? Is it ok if your partner does?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
18- How often do you drink alcohol? What is your favorite drink?
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
11- How about if they like a certain sports team? 12-How about drinking too much?
48~ Do you have any siblings? Are you close to your family?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Would you read them together?
39~ What are your love languages?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
17- Have you ever done drugs? Which ones? How often?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Do you like the “69” position? Do you prefer to be on top or bottom?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Doctor/Nurse Stripper/Client
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
You know that I will be 100% truthful, so ask.
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 is your view on sex? Meaning, When/Where/ How often/
89~ Do you like taking showers together?
Model/Photographer Police/Criminal
84~ How do you feel about reading/listening to adult stories?
81~ Do you have any kinks and/or fetishes?
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?
21- What's your favorite way to spend a weekend or time off?
Do you think this brought you closer together?
11- What's your favorite restaurant? What’s your least favorite?
What have you learned about yourself that you did not before this?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
I would allow you to do it… What would you do to me?
10~ How many dates are necessary before you to have sex with someone?
7- What if a person smells a certain way? 8- How about smoking?
33- If you could visit any time period, when would you pick? Please explain why?
90~ Have you ever had sex in a Pool or Hot Tub? Would 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,
5~ When you first started having sex, was it what you thought it would be?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
How old are you? Male or Female?
92~ Have you ever had or have an STD? How many? What was it?
3- What’s your favorite smell? Do you a least favorite?
*** Random Questions ***
49~ If you could, would you want to be the opposite sex for a day, week, or year?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
92~ Everyone needs a “safe” word. What is yours?
Over time has your thoughts on sex changed?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
52~ Are you willing to make “those types” of bets with your partner?
27- What was/ is nickname? Does it have a meaning behind it?
Family Relation Age Play
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…
Does the thought excite you? Care to share?
61~ How willing would you be to try new sexual positions?
10- What is your favorite family tradition? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
36- Do you play video games? What is your favorite? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
34~ Do you like the lights on or off during sex?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
13- What’s your favorite drink? What’s your least favorite?
Nothing too Serious
*** Questions About Me ***
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
15~ Have you ever been “in love”? Who? Care to Share?
Teacher/Student Stranger/One Night Stand
47~ What would be your dream job and why?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
What is your favorite toy? Ever wanted to try a specific toy?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
28~ What are some things that turn on? What is your biggest turn on?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts