What is the most interesting question you can ask to get to know someone?
Last Updated: 01.07.2025 15:33
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
13- How about having a certain hair cut/style?
Why do I feel like something bad is going to happen to me?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
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Nurse/Patient Celebrity/Fan
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Google Confirms Most Gmail Users Must Upgrade Accounts - Forbes
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Prisoner/Prison Guard Landlord/Tenant
92~ Everyone needs a “safe” word. What is yours?
What happen if all of a sudden a movie star decides to quit acting?
28- What are some things that people do that irritate you?
11~ Have you ever been caught by your parents or children or others while having sex?
8- What are your thoughts on politics?
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Would /have you ever given your partner a lap dance and Striptease?
*** Random Questions ***
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
65~ Describe the best orgasm you’ve ever had? Care to share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
21- What's your favorite way to spend a weekend or time off?
Alex Cooper Accuses Former Soccer Coach of Sexual Harassment in Call Her Alex - Vulture
17- Have you ever done drugs? Which ones? How often?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
18- How often do you drink alcohol? What is your favorite drink?
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Would you do it again, and would you rather 2 females or 2 males?
22- Do you have any birth marks? How about scars? Care to share how you got them?
51~ What tends to bring a smile to your face?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Get this wrong and this could mean the end… :-) some funny, some not…
Trump’s tax bill could raise taxes on foreign companies, hurting investment from abroad - AP News
*** Deal Breaker Questions ***
1- What was your first impression of me? Has it changed?
7- What are your thoughts on religion? Is there an afterlife?
President Trump kicked Zelensky out of the White House. Is it over for a deal?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
3- Should Pluto still be considered a planet? 4- How about smoking?
New Non-Opioid Drug Offers Powerful Pain Relief Without the Dangerous Side Effects - SciTechDaily
Model/Photographer Police/Criminal
80~ Share your top three fantasies/desires. (Be detailed) 😊
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
23- What is your dream job? What was it as a child?
76~ Have you had a threesome? Care to Share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
11- What's your favorite restaurant? What’s your least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
84~ How do you feel about reading/listening to adult stories?
Do you have a favorite? Is it ok if your partner does?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Do you like the “69” position? Do you prefer to be on top or bottom?
What do you dislike about me? I asked you to be 100% honest.
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?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
9- If you could have three wishes, what would they be? Why?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you like it when they show and tell you what they want?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
50~ How many children do you have? What are their ages?
11- List at least 5 things on your bucket list. Have you done any of them already?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
15- What's your favorite saying? What word or phrase is your least favorite?
Would you mind if your partner watched it? How about together vs alone?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
What would you say to prove to yourself that it was really you?
*** What’s Your Favorite…? ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What is your favorite position? Why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
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)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
42~ What’s your biggest regret in life?
34~ Do you like the lights on or off during sex?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
29- How superstitious are you?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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?
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- What’s your favorite color? Do you a least favorite?
7- What if a person smells a certain way? 8- How about smoking?
17- What’s your favorite holiday? What’s your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
19~ Who/when was your first “heartbreak”?
Master/Slave Boss/Maid
81~ Do you have any kinks and/or fetishes?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Does the thought excite you? Care to share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
3- What’s your favorite smell? Do you a least favorite?
36~ What is your favorite time of day to have sex/make love?
How old are you? Male or Female?
36- Do you play video games? What is your favorite? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
83~ How do you feel about Porn?
Can you Deep Throat? Do you like the taste of yourself?
39~ What are your love languages?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
10- List 5 of your top pet peeves.
38~ Share your most embarrassing sexual memory?
40~ What’s the weirdest place you’ve ever had sex?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What have you learned about yourself that you did not before this?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
20- What’s your favorite candy? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
22- What is your favorite childhood memory? What is your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
30~ What's something unexpected that turns you on?
60~ How important is oral sex? Do you like receiving? Do you like giving?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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…
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
33- If you could visit any time period, when would you pick? Please explain why?
37- Do you like your name? If you could change it, what would you change it too?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
29~ What are some things that turn you off? What is your biggest turn off?
3- What Superhero or Superpower would you want to be/have?
67~ Do you like it when your partner moans and/or is vocal during sex?
21~ What was the best date you ever went on? What has been the worst?
Will you cheat again? How can, you be sure? Define what cheating is to you.
33- Beach or Mountains? Or is there another place to like better?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
52~ Are you willing to make “those types” of bets with your partner?
* Give a rating for each one (0-100)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
If you win, what will you make them do?
If you say it, I will stop, and we can talk about it when you are ready.
47~ What would be your dream job and why?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Over time has your thoughts on sex changed?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
12- What is the weirdest thing you've ever eaten?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
What have you learned about me that was new and/or surprising?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
How well do you know me? And some of your thoughts about me
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
12- What’s your favorite food? What’s your least favorite?
*** Questions about Relationships/Past ***
48~ Do you have any siblings? Are you close to your family?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Have you ever? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
If YES, was it with 2 men or 2 women? Did you enjoy it?
8- What's your favorite flavor of ice cream? Do you a least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
15- What bad habit do you wish you could quit? Do you have any addictions?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
61~ How willing would you be to try new sexual positions?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
The Ice Breaker Questions
82~ Do you have any fantasies involving Role-Playing?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
How many times do you think you have “made love”?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
44~ Care to share something about yourself that no one else knows about you?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Any that are a turn off?
32- What's your greatest talent? Can I see it right now?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
I would allow you to do it… What would you do to me?
7-What do I do in bed that drives you wild? How about, what turns you off?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
18~ Who/when was your first “crush”?
If yes, what?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Nothing too Serious
What was the longest? What was the shortest?
Would you read them together?
That one or two things that made you go hmmmm, OMG or wow!
10- What is your favorite family tradition? What’s your least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
31- If given a chance to be immortal, would you take it? Why?
4- For a pet, Cat, dog or other?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
(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…)
13- What is the craziest/scariest thing you've ever done?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
1~ How old were you when you had your first kiss? 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?
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?
Do you watch it? What is your favorite?
*** Questions About Me ***
How many partners have you had oral sex with? Who? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
How about if they talk dirty and/or call you names?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
13- What’s your favorite drink? What’s your least favorite?
Do you think this brought you closer together?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
10~ How many dates are necessary before you to have sex with someone?
You know that I will be 100% truthful, so ask.
26~ What side of the bed do you sleep on?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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…
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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?
62~ Have you used adult toys?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
9~ How many times over your lifetime do you think you have had sex so far?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
5~ When you first started having sex, was it what you thought it would be?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What is your view on sex? Meaning, When/Where/ How often/
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,
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
9- What’s your favorite season and why? What’s your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Please share Did you stop?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
92~ Have you ever had or have an STD? How many? What was it?
Any that are a turn off?
Family Relation Age Play
Escort/Client Job Applicant/Hiring Manager
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
45~ How do you feel about me blindfolding you? How about blindfolding me?
89~ Do you like taking showers together?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Teacher/Student Stranger/One Night Stand
25~ How do you feel about PDA? (Public Display of Affection)
49~ How many times have you been married? Why did they end?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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?
70~ Would/do you have/like anal sex?
Doctor/Nurse Stripper/Client
What is your favorite toy? Ever wanted to try a specific toy?
28~ What are some things that turn on? What is your biggest turn on?
Would you allow me to clean every part of your body with my soapy hands and fingers?
53~ How much can you tell me about the one thing you are most passionate about?
27- What was/ is nickname? Does it have a meaning behind it?
15~ Have you ever been “in love”? Who? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
51~ Are you willing to play adult games with your partner?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
52~ What are your hobbies?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?