What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 07:19
*** Deal Breaker Questions ***
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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Teacher/Student Stranger/One Night Stand
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
23- What is your dream job? What was it as a child?
What is the one unconventional piece of Stoic advice that has significantly improved your life?
51~ Are you willing to play adult games with your partner?
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)
14- What's your favorite dessert? Do you a least favorite?
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20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
8- What are your thoughts on politics?
29- How superstitious are you?
Could Trump’s ‘big beautiful bill’ kill the OFR and accidentally sabotage SOFR? - Financial Times
92~ Everyone needs a “safe” word. What is yours?
1- What was your first impression of me? Has it changed?
60~ How important is oral sex? Do you like receiving? Do you like giving?
*** Questions About Me ***
11- What's your favorite restaurant? What’s your least favorite?
7- What are your thoughts on religion? Is there an afterlife?
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Prisoner/Prison Guard Landlord/Tenant
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
13- What is the craziest/scariest thing you've ever done?
Is it possible to become homeless after being released from jail or prison in the United States?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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28- What are some things that people do that irritate you?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
What is the worst name in Tolkien’s legendarium (meaning and look)?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
9~ How many times over your lifetime do you think you have had sex so far?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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5- What do I do outside the bedroom that turns you on? How about, what turns you off?
*** Random Questions ***
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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Get this wrong and this could mean the end… :-) some funny, some not…
12- What is the weirdest thing you've ever eaten?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
47~ What would be your dream job and why?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
I have a bad reputation and need help. What should I do?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
21- What's your favorite way to spend a weekend or time off?
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44~ Have you ever been tied up during sex? What are your thoughts on bondage?
76~ Have you had a threesome? Care to Share?
How old are you? Male or Female?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you watch it? What is your favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
81~ Do you have any kinks and/or fetishes?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
5~ When you first started having sex, was it what you thought it would be?
11~ Have you ever been caught by your parents or children or others while having sex?
61~ How willing would you be to try new sexual positions?
20- What’s your favorite candy? What’s your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
* Give a rating for each one (0-100)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Have you ever? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
11- List at least 5 things on your bucket list. Have you done any of them already?
17- Have you ever done drugs? Which ones? How often?
45~ How do you feel about me blindfolding you? How about blindfolding me?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If YES, was it with 2 men or 2 women? Did you enjoy it?
67~ Do you like it when your partner moans and/or is vocal during sex?
How about if they talk dirty and/or call you names?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Please share Did you stop?
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…
7-What do I do in bed that drives you wild? How about, what turns you off?
3- Should Pluto still be considered a planet? 4- How about smoking?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
36- Do you play video games? What is your favorite? Do you a least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
31- If given a chance to be immortal, would you take it? Why?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
If you win, what will you make them do?
*** What’s Your Favorite…? ***
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
7- What if a person smells a certain way? 8- How about smoking?
Would /have you ever given your partner a lap dance and Striptease?
48~ Have you ever paid or been paid for sex?
Would you do it again, and would you rather 2 females or 2 males?
10- What is your favorite family tradition? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
92~ Have you ever had or have an STD? How many? What was it?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
1- What’s your favorite animal? Do you a least favorite?
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- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
3- What Superhero or Superpower would you want to be/have?
What do you dislike about me? I asked you to be 100% honest.
15~ Have you ever been “in love”? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
38~ Share your most embarrassing sexual memory?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Doctor/Nurse Stripper/Client
9- If you could have three wishes, what would they be? Why?
The Ice Breaker Questions
36~ What is your favorite time of day to have sex/make love?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
53~ How much can you tell me about the one thing you are most passionate about?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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 like the “69” position? Do you prefer to be on top or bottom?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
52~ What are your hobbies?
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
That one or two things that made you go hmmmm, OMG or wow!
82~ Do you have any fantasies involving Role-Playing?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Family Relation Age Play
Master/Slave Boss/Maid
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
84~ How do you feel about reading/listening to adult stories?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
39~ What are your love languages?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
34~ Do you like the lights on or off during sex?
What is your favorite toy? Ever wanted to try a specific toy?
65~ Describe the best orgasm you’ve ever had? Care to share?
Any that are a turn off?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
70~ Would/do you have/like anal sex?
27- What was/ is nickname? Does it have a meaning behind it?
18- What’s your favorite way to relax after a long day? What’s your 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?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
22- What is your favorite childhood memory? What is your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
*** Questions about Relationships/Past ***
89~ Do you like taking showers together?
Do you think this brought you closer 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?
Would you mind if your partner watched it? How about together vs alone?
Any that are a turn off?
(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…)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Escort/Client Job Applicant/Hiring Manager
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
I would allow you to do it… What would you do to me?
18~ Who/when was your first “crush”?
Nothing too Serious
33- Beach or Mountains? Or is there another place to like better?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
42~ What’s your biggest regret in life?
83~ How do you feel about Porn?
26~ What side of the bed do you sleep on?
What is your view on sex? Meaning, When/Where/ How often/
What was the longest? What was the shortest?
49~ How many times have you been married? Why did they end?
Can you Deep Throat? Do you like the taste of yourself?
29~ What are some things that turn you off? What is your biggest turn off?
1~ How old were you when you had your first kiss? Who? Care to Share?
How many partners have you had oral sex with? Who? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
17- What’s your favorite holiday? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Would you read them together?
If you say it, I will stop, and we can talk about it when you are ready.
50~ How many children do you have? What are their ages?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
2- What’s your favorite color? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
48~ Do you have any siblings? Are you close to your family?
What is your favorite position? Why?
32- What's your greatest talent? Can I see it right now?
Do you have a favorite? Is it ok if your partner does?
51~ What tends to bring a smile to your face?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
6- Do you have dreams? Can you remember them? What do you usually dream about?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
13- How about having a certain hair cut/style?
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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
44~ Care to share something about yourself that no one else knows about you?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
19~ Who/when was your first “heartbreak”?
10~ How many dates are necessary before you to have sex with someone?
21~ What was the best date you ever went on? What has been the worst?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
What have you learned about yourself that you did not before this?
15- What bad habit do you wish you could quit? Do you have any addictions?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
How well do you know me? And some of your thoughts about me
9- Is there something you’ve always wanted to ask me but you’re afraid?
19- What’s your favorite fairytale? What’s your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
What would you say to prove to yourself that it was really you?
40~ What’s the weirdest place you’ve ever had sex?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Model/Photographer Police/Criminal
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
How many times do you think you have “made love”?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
19- Do/have you smoked? What do you prefer? How often?
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- What’s your favorite food? What’s your least favorite?
Do you like it when they show and tell you what they want?
9- What’s your favorite season and why? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
18- How often do you drink alcohol? What is your favorite drink?
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…
Nurse/Patient Celebrity/Fan
8- What's your favorite flavor of ice cream? Do you a least favorite?
30~ What's something unexpected that turns you on?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
You know that I will be 100% truthful, so ask.
Would you ever want to be woken up with oral and/or intercourse?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
10- List 5 of your top pet peeves.
5- Have you ever been hypnotized? Would you allow yourself to be?
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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Over time has your thoughts on sex changed?
If yes, what?
13- What’s your favorite drink? What’s your least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
62~ Have you used adult toys?
Does the thought excite you? Care to share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
71~ Would you give your partner a hand or foot job? Would you receive one?
33- If you could visit any time period, when would you pick? Please explain why?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What have you learned about me that was new and/or surprising?
4- For a pet, Cat, dog or other?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?