What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 01:18
If YES, was it with 2 men or 2 women? Did you enjoy it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
*** Questions about Relationships/Past ***
What's the cause of under eye dark circles and what treatments can help?
60~ How important is oral sex? Do you like receiving? Do you like giving?
What would you say to prove to yourself that it was really you?
48~ Have you ever paid or been paid for sex?
Scientists Discover Promising New Alzheimer’s Treatment - SciTechDaily
19~ Who/when was your first “heartbreak”?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
President Trump kicked Zelensky out of the White House. Is it over for a deal?
4- For a pet, Cat, dog or other?
1- What was your first impression of me? Has it changed?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Diddy trial day 18 recap: 2nd Combs victim concludes 'humiliating' cross-examination - ABC News
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Do you like the “69” position? Do you prefer to be on top or bottom?
What is your interpretation of the movie Rocky? What makes it a good film in your opinion?
What have you learned about me that was new and/or surprising?
49~ How many times have you been married? Why did they end?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Becky Lynch wins the Intercontinental title at Money in the Bank - Cageside Seats
29- How superstitious are you?
61~ How willing would you be to try new sexual positions?
9- What’s your favorite season and why? What’s your least favorite?
Senators get ready to roll out a new crypto bill - Politico
45~ How do you feel about me blindfolding you? How about blindfolding me?
Would /have you ever given your partner a lap dance and Striptease?
3- Should Pluto still be considered a planet? 4- How about smoking?
Listen to the eerie sounds of Mars recorded by a NASA rover - Mashable
52~ What are your hobbies?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Has any man licked his wife's vagina while another man had sex with her?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you have a favorite? Is it ok if your partner does?
Would you do it again, and would you rather 2 females or 2 males?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
Why did Obito, a supposed "bad person," do good things for Kakashi?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
25~ How do you feel about PDA? (Public Display of Affection)
53~ How much can you tell me about the one thing you are most passionate about?
The Club World Cup is finally up and running — and soccer may never be the same - AP News
31- If given a chance to be immortal, would you take it? Why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
You know that I will be 100% truthful, so ask.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Do you like it when they show and tell you what they want?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
34~ Do you like the lights on or off during 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…
81~ Do you have any kinks and/or fetishes?
36- Do you play video games? What is your favorite? Do you a least favorite?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Nothing too Serious
51~ What tends to bring a smile to your face?
67~ Do you like it when your partner moans and/or is vocal during sex?
That one or two things that made you go hmmmm, OMG or wow!
19- Do/have you smoked? What do you prefer? How often?
80~ Share your top three fantasies/desires. (Be detailed) 😊
13- How about having a certain hair cut/style?
Over time has your thoughts on sex changed?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
How many partners have you had oral sex with? Who? Care to Share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
5- Have you ever been hypnotized? Would you allow yourself to be?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Repairman/Lonely Wife Virgin/Experienced
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
6- Do you have dreams? Can you remember them? What do you usually dream about?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
3- What’s your favorite smell? Do you a least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
What do you dislike about me? I asked you to be 100% honest.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
21~ What was the best date you ever went on? What has been the worst?
18- How often do you drink alcohol? What is your favorite drink?
13- What is the craziest/scariest thing you've ever done?
15- What bad habit do you wish you could quit? Do you have any addictions?
5~ When you first started having sex, was it what you thought it would be?
Would you mind if your partner watched it? How about together vs alone?
1~ How old were you when you had your first kiss? Who? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
33- Beach or Mountains? Or is there another place to like better?
10- List 5 of your top pet peeves.
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
How many times do you think you have “made love”?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
92~ Have you ever had or have an STD? How many? What was it?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
12- What’s your favorite food? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
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)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Would you allow me to clean every part of your body with my soapy hands and fingers?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
20- What’s your favorite candy? What’s your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
33- If you could visit any time period, when would you pick? Please explain why?
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?
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,
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What have you learned about yourself that you did not before this?
Master/Slave Boss/Maid
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
89~ Do you like taking showers together?
*** What’s Your Favorite…? ***
11- What's your favorite restaurant? What’s your least favorite?
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?
If yes, what?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
9- Is there something you’ve always wanted to ask me but you’re afraid?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
44~ Care to share something about yourself that no one else knows about you?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
9~ How many times over your lifetime do you think you have had sex so far?
7-What do I do in bed that drives you wild? How about, what turns you off?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Please share Did you stop?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
71~ Would you give your partner a hand or foot job? Would you receive one?
29~ What are some things that turn you off? What is your biggest turn off?
Doctor/Nurse Stripper/Client
36~ What is your favorite time of day to have sex/make love?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
22- What is your favorite childhood memory? What is your least favorite?
18~ Who/when was your first “crush”?
28- What are some things that people do that irritate you?
Any that are a turn off?
What is your favorite position? Why?
21- What's your favorite way to spend a weekend or time off?
34- Ever been to a concert? What was your favorite? Who would you like to see?
14- What's your favorite dessert? Do you a least favorite?
51~ Are you willing to play adult games with your partner?
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…
1- What’s your favorite animal? Do you a least favorite?
50~ How many children do you have? What are their ages?
(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…)
28~ What are some things that turn on? What is your biggest turn on?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
76~ Have you had a threesome? Care to Share?
Do you think this brought you closer together?
37- Do you like your name? If you could change it, what would you change it too?
32- What's your greatest talent? Can I see it right now?
Model/Photographer Police/Criminal
10- What is your favorite family tradition? What’s your least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
How old are you? Male or Female?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
3- What Superhero or Superpower would you want to be/have?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Family Relation Age Play
14- What is an embarrassing moment in your life? How about your most embarrassing?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
What is your view on sex? Meaning, When/Where/ How often/
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Do you watch it? What is your favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
If you win, what will you make them do?
15~ Have you ever been “in love”? Who? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
39~ What are your love languages?
*** Deal Breaker Questions ***
11- List at least 5 things on your bucket list. Have you done any of them already?
I would allow you to do it… What would you do to me?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
Can you Deep Throat? Do you like the taste of yourself?
9- If you could have three wishes, what would they be? Why?
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?
7- What if a person smells a certain way? 8- How about smoking?
Prisoner/Prison Guard Landlord/Tenant
13~ Is there a difference between, making love, having sex, and fucking?
Have you ever? Care to Share?
7- What’s your favorite book? Do you have a favorite genre? 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?
26~ What side of the bed do you sleep on?
How well do you know me? And some of your thoughts about me
What was the longest? What was the shortest?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
65~ Describe the best orgasm you’ve ever had? Care to share?
40~ What’s the weirdest place you’ve ever had sex?
83~ How do you feel about Porn?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
38~ Share your most embarrassing sexual memory?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Teacher/Student Stranger/One Night Stand
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Does the thought excite you? Care to share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
42~ What’s your biggest regret in life?
17- Have you ever done drugs? Which ones? How often?
*** Questions About Me ***
Would you read them together?
11- How about if they like a certain sports team? 12-How about drinking too much?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
62~ Have you used adult toys?
Would you ever want to be woken up with oral and/or intercourse?
23- What is your dream job? What was it as a child?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
70~ Would/do you have/like anal sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
19- What’s your favorite fairytale? 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.?
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?
Any that are a turn off?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
2- What’s your favorite color? Do you a least favorite?
How about if they talk dirty and/or call you names?
27- What was/ is nickname? Does it have a meaning behind it?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
* Give a rating for each one (0-100)
84~ How do you feel about reading/listening to adult stories?
7- What are your thoughts on religion? Is there an afterlife?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
The Ice Breaker Questions
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
8- What's your favorite flavor of ice cream? Do you a least favorite?
17- What’s your favorite holiday? What’s your least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Escort/Client Job Applicant/Hiring Manager
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Nurse/Patient Celebrity/Fan
If NO, would you ever have one? Would it be with 2 men or 2 women?
82~ Do you have any fantasies involving Role-Playing?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
12- What is the weirdest thing you've ever eaten?
47~ What would be your dream job and why?
Get this wrong and this could mean the end… :-) some funny, some not…
15- What's your favorite saying? What word or phrase is your least favorite?
8- What are your thoughts on politics?
10~ How many dates are necessary before you to have sex with someone?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
What is your favorite toy? Ever wanted to try a specific toy?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
*** Random Questions ***