What is the most interesting question you can ask to get to know someone?
Last Updated: 27.06.2025 01:50
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
At least 8 dead in shooting near Israeli and US-supported aid sites in Gaza - NPR
24~ What are your expectations in a relationship? (I know a very big question, take your time)
38~ Share your most embarrassing sexual memory?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
If yes, what?
*** Deal Breaker Questions ***
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?
15- What bad habit do you wish you could quit? Do you have any addictions?
That one or two things that made you go hmmmm, OMG or wow!
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?
17- Have you ever done drugs? Which ones? How often?
8- What are your thoughts on politics?
“Very Odd” New Sea Monster Identified After Decades of Mystery - SciTechDaily
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…
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
What is a good way to conduct an interview?
65~ Describe the best orgasm you’ve ever had? Care to share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Weight loss connected to nerve cells in the brain, study finds - The Brighter Side of News
9~ How many times over your lifetime do you think you have had sex so far?
13~ Is there a difference between, making love, having sex, and fucking?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What should I do if I love a girl and she apparently doesn't love me?
44~ Care to share something about yourself that no one else knows about you?
What have you learned about me that was new and/or surprising?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Dave Chappelle and Mo Amer on Politics and Comedy, SNL Monologues - Variety
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
53~ How much can you tell me about the one thing you are most passionate about?
Prisoner/Prison Guard Landlord/Tenant
Yvette Cooper yet to agree deal three days before spending review - BBC
49~ If you could, would you want to be the opposite sex for a day, week, or year?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
89~ Do you like taking showers together?
Over time has your thoughts on sex changed?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
*** Random Questions ***
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
45~ How do you feel about me blindfolding you? How about blindfolding me?
NASA Pulls the Plug on Europa Lander, but Scientists Propose a Plan B - Gizmodo
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
76~ Have you had a threesome? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
61~ How willing would you be to try new sexual positions?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Model/Photographer Police/Criminal
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
9- If you could have three wishes, what would they be? Why?
21- What's your favorite way to spend a weekend or time off?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
If you say it, I will stop, and we can talk about it when you are ready.
Teacher/Student Stranger/One Night Stand
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
11- What's your favorite restaurant? What’s your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
* Give a rating for each one (0-100)
23- What is your dream job? What was it as a child?
15- What's your favorite saying? What word or phrase is your least favorite?
If you win, what will you make them do?
Would you allow me to clean every part of your body with my soapy hands and fingers?
22- Do you have any birth marks? How about scars? Care to share how you got them?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
19- What’s your favorite fairytale? What’s your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
11- List at least 5 things on your bucket list. Have you done any of them already?
13- What’s your favorite drink? What’s your least favorite?
19~ Who/when was your first “heartbreak”?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
71~ Would you give your partner a hand or foot job? Would you receive one?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What have you learned about yourself that you did not before this?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Repairman/Lonely Wife Virgin/Experienced
4- For a pet, Cat, dog or other?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
10~ How many dates are necessary before you to have sex with someone?
1- What’s your favorite animal? Do you a least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
50~ How many children do you have? What are their ages?
51~ What tends to bring a smile to your face?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
10- List 5 of your top pet peeves.
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)
How many times do you think you have “made love”?
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)?
29- How superstitious are you?
21~ What was the best date you ever went on? What has been the worst?
92~ Everyone needs a “safe” word. What is yours?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Would /have you ever given your partner a lap dance and Striptease?
(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…)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
2- What’s your favorite color? Do you a least favorite?
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?
Any that are a turn off?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
22- What is your favorite childhood memory? What is your least favorite?
What was the longest? What was the shortest?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
34- Ever been to a concert? What was your favorite? Who would you like to see?
47~ What would be your dream job and why?
15~ Have you ever been “in love”? Who? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
62~ Have you used adult toys?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
42~ What’s your biggest regret in life?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Do you watch it? What is your favorite?
39~ What are your love languages?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
5~ When you first started having sex, was it what you thought it would be?
Does the thought excite you? Care to share?
84~ How do you feel about reading/listening to adult stories?
32- What's your greatest talent? Can I see it right now?
27- What was/ is nickname? Does it have a meaning behind it?
You know that I will be 100% truthful, so ask.
How well do you know me? And some of your thoughts about me
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Please share Did you stop?
Have you ever? Care to Share?
*** What’s Your Favorite…? ***
31- If given a chance to be immortal, would you take it? Why?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
What is your favorite position? Why?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
11- How about if they like a certain sports team? 12-How about drinking too much?
*** Questions about Relationships/Past ***
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?
Would you read them together?
36~ What is your favorite time of day to have sex/make love?
33- Beach or Mountains? Or is there another place to like better?
Escort/Client Job Applicant/Hiring Manager
52~ Are you willing to make “those types” of bets with your partner?
82~ Do you have any fantasies involving Role-Playing?
33- If you could visit any time period, when would you pick? Please explain why?
12- What is the weirdest thing you've ever eaten?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What is your view on sex? Meaning, When/Where/ How often/
51~ Are you willing to play adult games with your partner?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Get this wrong and this could mean the end… :-) some funny, some not…
25~ How do you feel about PDA? (Public Display of Affection)
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?
40~ What’s the weirdest place you’ve ever had sex?
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…
Any that are a turn off?
Do you think this brought you closer together?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
What would you say to prove to yourself that it was really you?
Do you have a favorite? Is it ok if your partner does?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Would you ever want to be woken up with oral and/or intercourse?
Nurse/Patient Celebrity/Fan
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?
81~ Do you have any kinks and/or fetishes?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Do you like it when they show and tell you what they want?
14- What is an embarrassing moment in your life? How about your most embarrassing?
92~ Have you ever had or have an STD? How many? What was it?
28- What are some things that people do that irritate you?
What do you dislike about me? I asked you to be 100% honest.
13- How about having a certain hair cut/style?
20- What’s your favorite candy? What’s your 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?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
30~ What's something unexpected that turns you on?
How old are you? Male or Female?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
28~ What are some things that turn on? What is your biggest turn on?
Would you mind if your partner watched it? How about together vs alone?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Master/Slave Boss/Maid
13- What is the craziest/scariest thing you've ever done?
8- What's your favorite flavor of ice cream? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
80~ Share your top three fantasies/desires. (Be detailed) 😊
18- How often do you drink alcohol? What is your favorite drink?
48~ Have you ever paid or been paid for sex?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
7- What if a person smells a certain way? 8- How about smoking?
7- What are your thoughts on religion? Is there an afterlife?
18~ Who/when was your first “crush”?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
I would allow you to do it… What would you do to me?
48~ Do you have any siblings? Are you close to your family?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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,
36- Do you play video games? What is your favorite? Do you a least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
1~ How old were you when you had your first kiss? Who? Care to Share?
3- What Superhero or Superpower would you want to be/have?
83~ How do you feel about Porn?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
10- What is your favorite family tradition? What’s your least favorite?
52~ What are your hobbies?
12- What’s your favorite food? What’s your least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
Would you do it again, and would you rather 2 females or 2 males?
70~ Would/do you have/like anal sex?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
*** Questions About Me ***
If YES, was it with 2 men or 2 women? Did you enjoy it?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
6- Do you have dreams? Can you remember them? What do you usually dream about?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
7-What do I do in bed that drives you wild? How about, what turns you off?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
How many partners have you had oral sex with? Who? Care to Share?
49~ How many times have you been married? Why did they end?
The Ice Breaker Questions
Will you cheat again? How can, you be sure? Define what cheating is to you.
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
9- What’s your favorite season and why? What’s your least favorite?
3- What’s your favorite smell? Do you a least favorite?
How about if they talk dirty and/or call you names?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
5- Have you ever been hypnotized? Would you allow yourself to be?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
26~ What side of the bed do you sleep on?
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?
Can you Deep Throat? Do you like the taste of yourself?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Nothing too Serious
37- Do you like your name? If you could change it, what would you change it too?
14- What's your favorite dessert? Do you a least favorite?
19- Do/have you smoked? What do you prefer? How often?
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?
Family Relation Age Play