What is the most interesting question you can ask to get to know someone?
Last Updated: 29.06.2025 01:20
*** Deal Breaker Questions ***
11- What's your favorite restaurant? What’s your least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Evidence piles up that Trump's tariffs are crushing job market - Daily Kos
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
Repairman/Lonely Wife Virgin/Experienced
Does having the wrong address on my car insurance invalidate my policy?
If you say it, I will stop, and we can talk about it when you are ready.
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Reds Sign Wade Miley, Place Hunter Greene On Injured List - MLB Trade Rumors
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
61~ How willing would you be to try new sexual positions?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
What Happens to Your Body When You Eat Watermelon Regularly - Verywell Health
52~ Are you willing to make “those types” of bets with your partner?
9- If you could have three wishes, what would they be? Why?
Any that are a turn off?
Has the current political environment caused Canadians to cancel trips to the United States?
28- What are some things that people do that irritate you?
21- What's your favorite way to spend a weekend or time off?
84~ How do you feel about reading/listening to adult stories?
48~ Do you have any siblings? Are you close to your family?
25~ How do you feel about PDA? (Public Display of Affection)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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?
Nothing too Serious
Family Relation Age Play
32- What's your greatest talent? Can I see it right now?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Quantum Time-Freeze: Lasers Lock Quantum States 1,000x Longer - SciTechDaily
Will you cheat again? How can, you be sure? Define what cheating is to you.
8- What are your thoughts on politics?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Breast transplanted to replace cancerous one in 'world first' operation - BBC
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
67~ Do you like it when your partner moans and/or is vocal during sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
44~ Care to share something about yourself that no one else knows about you?
How often should you use red light therapy?
14- What's your favorite dessert? Do you a least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
19- What’s your favorite fairytale? What’s your least favorite?
The Ice Breaker Questions
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Would /have you ever given your partner a lap dance and Striptease?
If you win, what will you make them do?
Escort/Client Job Applicant/Hiring Manager
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Model/Photographer Police/Criminal
9- What’s your favorite season and why? What’s your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
11- How about if they like a certain sports team? 12-How about drinking too much?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
39~ What are your love languages?
What have you learned about me that was new and/or surprising?
92~ Everyone needs a “safe” word. What is yours?
22- What is your favorite childhood memory? What is your least favorite?
21~ What was the best date you ever went on? What has been the worst?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
7-What do I do in bed that drives you wild? How about, what turns you off?
12- What’s your favorite food? What’s your least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
7- What if a person smells a certain way? 8- How about smoking?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
29- How superstitious are you?
10~ How many dates are necessary before you to have sex with someone?
How well do you know me? And some of your thoughts about me
1- What’s your favorite animal? Do you a least favorite?
83~ How do you feel about Porn?
I would allow you to do it… What would you do to me?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
Would you read them together?
81~ Do you have any kinks and/or fetishes?
36- Do you play video games? What is your favorite? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
71~ Would you give your partner a hand or foot job? Would you receive one?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Do you watch it? What is your favorite?
13- How about having a certain hair cut/style?
Please share Did you stop?
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 is your favorite toy? Ever wanted to try a specific toy?
You know that I will be 100% truthful, so ask.
70~ Would/do you have/like anal sex?
What have you learned about yourself that you did not before this?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
18~ Who/when was your first “crush”?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
38~ Share your most embarrassing sexual memory?
What do you dislike about me? I asked you to be 100% honest.
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Can you Deep Throat? Do you like the taste of yourself?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
37- Do you like your name? If you could change it, what would you change it too?
30~ What's something unexpected that turns you on?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
26~ What side of the bed do you sleep on?
62~ Have you used adult toys?
23- What is your dream job? What was it as a child?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Does the thought excite you? 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?
31- If given a chance to be immortal, would you take it? Why?
How many partners have you had oral sex with? Who? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Would you do it again, and would you rather 2 females or 2 males?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
15- What bad habit do you wish you could quit? Do you have any addictions?
50~ How many children do you have? What are their ages?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
51~ What tends to bring a smile to your face?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Doctor/Nurse Stripper/Client
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…
Would you allow me to clean every part of your body with my soapy hands and fingers?
3- What Superhero or Superpower would you want to be/have?
13- What’s your favorite drink? What’s your least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
48~ Have you ever paid or been paid for sex?
2- What’s your favorite color? Do you a least favorite?
Master/Slave Boss/Maid
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
If NO, would you ever have one? Would it be with 2 men or 2 women?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
*** Random Questions ***
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would you mind if your partner watched it? How about together vs alone?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Over time has your thoughts on sex changed?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
89~ Do you like taking showers together?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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)
52~ What are your hobbies?
3- Should Pluto still be considered a planet? 4- How about smoking?
34- Ever been to a concert? What was your favorite? Who would you like to see?
42~ What’s your biggest regret in life?
49~ How many times have you been married? Why did they end?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
17- Have you ever done drugs? Which ones? How often?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
11~ Have you ever been caught by your parents or children or others while having sex?
Teacher/Student Stranger/One Night Stand
36~ What is your favorite time of day to have sex/make love?
5~ When you first started having sex, was it what you thought it would be?
47~ What would be your dream job and why?
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…
76~ Have you had a threesome? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
35- Do you like playing board or cards game? 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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
18- How often do you drink alcohol? What is your favorite drink?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
Nurse/Patient Celebrity/Fan
Prisoner/Prison Guard Landlord/Tenant
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
3- What’s your favorite smell? Do you a least favorite?
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,
28~ What are some things that turn on? What is your biggest turn on?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Do you like the “69” position? Do you prefer to be on top or bottom?
(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…)
Have you ever? Care to Share?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
82~ Do you have any fantasies involving Role-Playing?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
17- What’s your favorite holiday? What’s your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
* Give a rating for each one (0-100)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
How about if they talk dirty and/or call you names?
1- What was your first impression of me? Has it changed?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
1~ How old were you when you had your first kiss? Who? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
4- For a pet, Cat, dog or other?
27- What was/ is nickname? Does it have a meaning behind it?
Do you have a favorite? Is it ok if your partner does?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
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?
13- What is the craziest/scariest thing you've ever done?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
29~ What are some things that turn you off? What is your biggest turn off?
51~ Are you willing to play adult games with your partner?
How old are you? Male or Female?
12- What is the weirdest thing you've ever eaten?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
That one or two things that made you go hmmmm, OMG or wow!
Any that are a turn off?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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 was the longest? What was the shortest?
92~ Have you ever had or have an STD? How many? What was it?
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....)
If yes, what?
15- What's your favorite saying? What word or phrase is your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
40~ What’s the weirdest place you’ve ever had sex?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
11- List at least 5 things on your bucket list. Have you done any of them already?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What is your favorite position? Why?
34~ Do you like the lights on or off during sex?
What would you say to prove to yourself that it was really you?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
19~ Who/when was your first “heartbreak”?
10- List 5 of your top pet peeves.
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
*** Questions about Relationships/Past ***
*** Questions About Me ***
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Get this wrong and this could mean the end… :-) some funny, some not…
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
8- What's your favorite flavor of ice cream? Do you a least favorite?
Do you like it when they show and tell you what they want?
How many times do you think you have “made love”?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
*** What’s Your Favorite…? ***
Do you think this brought you closer together?