What is the most interesting question you can ask to get to know someone?
Last Updated: 29.06.2025 01:53
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
What have you learned about yourself that you did not before this?
How to reduce the age of the heart by 20 years - Times of India
That one or two things that made you go hmmmm, OMG or wow!
How many times do you think you have “made love”?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Former church in Northern Kentucky now a heavenly home for sale - WWMT
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Get this wrong and this could mean the end… :-) some funny, some not…
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Jimmy Buffett's Wife Files to Remove Co-Trustee on $275 Million Estate - Variety
53~ How much can you tell me about the one thing you are most passionate about?
25~ How do you feel about PDA? (Public Display of Affection)
1- What’s your favorite animal? Do you a least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How are you spending your best time?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
60~ How important is oral sex? Do you like receiving? Do you like giving?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What are the best Jewish jokes?
92~ Everyone needs a “safe” word. What is yours?
11~ Have you ever been caught by your parents or children or others while having sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
What should I do? I'm 17 and I'm dating a 23-year-old guy.
10- What is your favorite family tradition? What’s your least favorite?
13- How about having a certain hair cut/style?
33- If you could visit any time period, when would you pick? Please explain why?
A new type of X-point radiator that prevents tokamaks from overheating - Phys.org
Do you have a favorite? Is it ok if your partner does?
*** Deal Breaker Questions ***
51~ What tends to bring a smile to your face?
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~ What is the average length of your relationship(s)? What was the longest? Why did they end?
What would you say to prove to yourself that it was really you?
Palantir's stock price surges on AI news, gamma squeeze - TheStreet
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
48~ Have you ever paid or been paid for sex?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7- What are your thoughts on religion? Is there an afterlife?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
Diddy trial day 18 recap: 2nd Combs victim concludes 'humiliating' cross-examination - ABC News
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
27- What was/ is nickname? Does it have a meaning behind it?
Do you like it when they show and tell you what they want?
Have you ever dealt with a Christian narcissist?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Have you ever? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
What exactly is female squirting? Is it only urine or a combination of liquids?
What is your favorite toy? Ever wanted to try a specific toy?
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…
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
A Giant Hole Just Opened in The Sun – And It's Blasting Earth With Solar Wind - ScienceAlert
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Doctor/Nurse Stripper/Client
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- List 5 of your top pet peeves.
62~ Have you used adult toys?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
11- List at least 5 things on your bucket list. Have you done any of them already?
9- If you could have three wishes, what would they be? Why?
34~ Do you like the lights on or off during sex?
3- What Superhero or Superpower would you want to be/have?
5~ When you first started having sex, was it what you thought it would be?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
13~ Is there a difference between, making love, having sex, and fucking?
84~ How do you feel about reading/listening to adult stories?
Do you watch it? What is your favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
39~ What are your love languages?
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.
If yes, what?
30~ What's something unexpected that turns you on?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
19~ Who/when was your first “heartbreak”?
6- Do you have dreams? Can you remember them? What do you usually dream about?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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?
1~ How old were you when you had your first kiss? Who? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would you do it again, and would you rather 2 females or 2 males?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What was the longest? What was the shortest?
Over time has your thoughts on sex changed?
If you say it, I will stop, and we can talk about it when you are ready.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Do you like the “69” position? Do you prefer to be on top or bottom?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Would you ever want to be woken up with oral and/or intercourse?
61~ How willing would you be to try new sexual positions?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
12- What’s your favorite food? What’s your least favorite?
Nurse/Patient Celebrity/Fan
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,
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Does the thought excite you? Care to share?
67~ Do you like it when your partner moans and/or is vocal during sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
I would allow you to do it… What would you do to me?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Repairman/Lonely Wife Virgin/Experienced
How about if they talk dirty and/or call you names?
1- What was your first impression of me? Has it changed?
Escort/Client Job Applicant/Hiring Manager
3- What’s your favorite smell? Do you a least favorite?
What is your favorite position? Why?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
81~ Do you have any kinks and/or fetishes?
10~ How many dates are necessary before you to have sex with someone?
*** Random Questions ***
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
20- What’s your favorite candy? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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…
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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?
19- What’s your favorite fairytale? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
82~ Do you have any fantasies involving Role-Playing?
Would you mind if your partner watched it? How about together vs alone?
29- How superstitious are you?
How old are you? Male or Female?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
7- What if a person smells a certain way? 8- How about smoking?
76~ Have you had a threesome? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
2- What’s your favorite color? Do you a least favorite?
Teacher/Student Stranger/One Night Stand
42~ What’s your biggest regret in life?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
15- What's your favorite saying? What word or phrase is your least favorite?
17- What’s your favorite holiday? What’s your least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
4- For a pet, Cat, dog or other?
14- What's your favorite dessert? Do you a least favorite?
Please share Did you stop?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
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?
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Nothing too Serious
37- Do you like your name? If you could change it, what would you change it too?
Would you read them together?
11- What's your favorite restaurant? What’s your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
36- Do you play video games? What is your favorite? Do you a least favorite?
Would /have you ever given your partner a lap dance and Striptease?
*** What’s Your Favorite…? ***
*** Questions About Me ***
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What have you learned about me that was new and/or surprising?
Would you allow me to clean every part of your body with my soapy hands and fingers?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
52~ Are you willing to make “those types” of bets with your partner?
70~ Would/do you have/like anal sex?
48~ Do you have any siblings? Are you close to your family?
13- What’s your favorite drink? What’s your least favorite?
32- What's your greatest talent? Can I see it right now?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
11- How about if they like a certain sports team? 12-How about drinking too much?
How many partners have you had oral sex with? Who? Care to Share?
89~ Do you like taking showers together?
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?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
38~ Share your most embarrassing sexual memory?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
52~ What are your hobbies?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Do you think this brought you closer together?
9- Is there something you’ve always wanted to ask me but you’re afraid?
8- What's your favorite flavor of ice cream? Do you a least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
36~ What is your favorite time of day to have sex/make love?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Model/Photographer Police/Criminal
Any that are a turn off?
28- What are some things that people do that irritate you?
The Ice Breaker Questions
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.
5- Have you ever been hypnotized? Would you allow yourself to be?
23- What is your dream job? What was it as a child?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
*** Questions about Relationships/Past ***
If YES, was it with 2 men or 2 women? Did you enjoy it?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
22- What is your favorite childhood memory? What is your least favorite?
You know that I will be 100% truthful, so ask.
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
(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…)
33- Beach or Mountains? Or is there another place to like better?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
49~ How many times have you been married? Why did they end?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
80~ Share your top three fantasies/desires. (Be detailed) 😊
18- What’s your favorite way to relax after a long day? What’s your least favorite?
17- Have you ever done drugs? Which ones? How often?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
3- Should Pluto still be considered a planet? 4- How about smoking?
51~ Are you willing to play adult games with your partner?
47~ What would be your dream job and why?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
13- What is the craziest/scariest thing you've ever done?
21~ What was the best date you ever went on? What has been the worst?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
9~ How many times over your lifetime do you think you have had sex so far?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Can you Deep Throat? Do you like the taste of yourself?
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)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Family Relation Age Play
18~ Who/when was your first “crush”?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
34- Ever been to a concert? What was your favorite? Who would you like to see?
If you win, what will you make them do?
Prisoner/Prison Guard Landlord/Tenant
21- What's your favorite way to spend a weekend or time off?
8- What are your thoughts on politics?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
12- What is the weirdest thing you've ever eaten?
Any that are a turn off?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Master/Slave Boss/Maid
28~ What are some things that turn on? What is your biggest turn on?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
9- What’s your favorite season and why? What’s your least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
83~ How do you feel about Porn?
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?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
50~ How many children do you have? What are their ages?
19- Do/have you smoked? What do you prefer? How often?
15- What bad habit do you wish you could quit? Do you have any addictions?
What is your view on sex? Meaning, When/Where/ How often/
18- How often do you drink alcohol? What is your favorite drink?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
45~ How do you feel about me blindfolding you? How about blindfolding me?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
How well do you know me? And some of your thoughts about me
44~ Care to share something about yourself that no one else knows about you?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
* Give a rating for each one (0-100)
26~ What side of the bed do you sleep on?