What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 01:18
*** Questions about Relationships/Past ***
What is your view on sex? Meaning, When/Where/ How often/
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
28- What are some things that people do that irritate you?
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)
Muon g-2 announces most precise measurement of the magnetic anomaly of the muon - Fermilab (.gov)
67~ Do you like it when your partner moans and/or is vocal during sex?
51~ Are you willing to play adult games with your partner?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
13- How about having a certain hair cut/style?
This STD is nearly 30 times worse in Onondaga County than it was 20 years ago - Syracuse.com
Would you mind if your partner watched it? How about together vs alone?
Please share Did you stop?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Stocks Rise as Oil Fades and Fed Bets Sink Yields: Markets Wrap - Bloomberg.com
Do you watch it? What is your favorite?
25~ How do you feel about PDA? (Public Display of Affection)
Over time has your thoughts on sex changed?
You probably don’t need foods with added protein, nutritionists say - NewsNation
What have you learned about me that was new and/or surprising?
What do you dislike about me? I asked you to be 100% honest.
If YES, was it with 2 men or 2 women? Did you enjoy it?
1- What was your first impression of me? Has it changed?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
1- What’s your favorite animal? Do you a least favorite?
Ask Ethan: What would the Universe be like without dark matter? - Big Think
*** What’s Your Favorite…? ***
28~ What are some things that turn on? What is your biggest turn on?
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?
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11- What's your favorite restaurant? What’s your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
60~ How important is oral sex? Do you like receiving? Do you like giving?
38~ Share your most embarrassing sexual memory?
11- List at least 5 things on your bucket list. Have you done any of them already?
30~ What's something unexpected that turns you on?
You know that I will be 100% truthful, so ask.
If you say it, I will stop, and we can talk about it when you are ready.
Do you think this brought you closer together?
18~ Who/when was your first “crush”?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Would you date/marry a guy younger than you? If no, why not?
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?
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…
Prisoner/Prison Guard Landlord/Tenant
What did your sister do to you that you can never forget?
65~ Describe the best orgasm you’ve ever had? Care to share?
15~ Have you ever been “in love”? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
10- What is your favorite family tradition? 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.?
36- Do you play video games? What is your favorite? Do you a least favorite?
8- What are your thoughts on politics?
7-What do I do in bed that drives you wild? How about, what turns you off?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
*** Questions About Me ***
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
48~ Do you have any siblings? Are you close to your family?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
82~ Do you have any fantasies involving Role-Playing?
Any that are a turn off?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
That one or two things that made you go hmmmm, OMG or wow!
I would allow you to do it… What would you do to me?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What would you say to prove to yourself that it was really you?
89~ Do you like taking showers together?
44~ Care to share something about yourself that no one else knows about you?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
5~ When you first started having sex, was it what you thought it would be?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Do you like it when they show and tell you what they want?
1~ How old were you when you had your first kiss? 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…
21- What's your favorite way to spend a weekend or time off?
Do you have a favorite? Is it ok if your partner does?
76~ Have you had a threesome? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
13- What is the craziest/scariest thing you've ever done?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
22- What is your favorite childhood memory? What is your least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
* Give a rating for each one (0-100)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
The Ice Breaker Questions
48~ Have you ever paid or been paid for sex?
39~ What are your love languages?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
83~ How do you feel about Porn?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Nurse/Patient Celebrity/Fan
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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,
49~ If you could, would you want to be the opposite sex for a day, week, or year?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
*** Deal Breaker Questions ***
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
3- What’s your favorite smell? Do you a least favorite?
50~ How many children do you have? What are their ages?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
7- What are your thoughts on religion? Is there an afterlife?
9- Is there something you’ve always wanted to ask me but you’re afraid?
33- Beach or Mountains? Or is there another place to like better?
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
Teacher/Student Stranger/One Night Stand
19~ Who/when was your first “heartbreak”?
19- What’s your favorite fairytale? What’s your least favorite?
If you win, what will you make them do?
What have you learned about yourself that you did not before this?
Would you ever want to be woken up with oral and/or intercourse?
How many times do you think you have “made love”?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
26~ What side of the bed do you sleep on?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
Family Relation Age Play
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
29~ What are some things that turn you off? What is your biggest turn off?
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?
92~ Have you ever had or have an STD? How many? What was it?
37- Do you like your name? If you could change it, what would you change it too?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
14- What's your favorite dessert? Do you a least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
52~ Are you willing to make “those types” of bets with your partner?
61~ How willing would you be to try new sexual positions?
Can you Deep Throat? Do you like the taste of yourself?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
45~ How do you feel about me blindfolding you? How about blindfolding me?
17- Have you ever done drugs? Which ones? How often?
40~ What’s the weirdest place you’ve ever had sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
8- What's your favorite flavor of ice cream? Do you a least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
What is your favorite toy? Ever wanted to try a specific toy?
5- Have you ever been hypnotized? Would you allow yourself to be?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
84~ How do you feel about reading/listening to adult stories?
33- If you could visit any time period, when would you pick? Please explain why?
If yes, what?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
19- Do/have you smoked? What do you prefer? How often?
11~ Have you ever been caught by your parents or children or others while having sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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?
Escort/Client Job Applicant/Hiring Manager
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
81~ Do you have any kinks and/or fetishes?
7- What if a person smells a certain way? 8- How about smoking?
Doctor/Nurse Stripper/Client
49~ How many times have you been married? Why did they end?
Would you read them together?
Any that are a turn off?
10- List 5 of your top pet peeves.
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
How old are you? Male or Female?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Does the thought excite you? Care to share?
Master/Slave Boss/Maid
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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 do it again, and would you rather 2 females or 2 males?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Would /have you ever given your partner a lap dance and Striptease?
15- What bad habit do you wish you could quit? Do you have any addictions?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
92~ Everyone needs a “safe” word. What is yours?
21~ What was the best date you ever went on? What has been the worst?
Model/Photographer Police/Criminal
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
42~ What’s your biggest regret in life?
12- What’s your favorite food? What’s your least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
*** Random Questions ***
12- What is the weirdest thing you've ever eaten?
9- If you could have three wishes, what would they be? Why?
47~ What would be your dream job and why?
13~ Is there a difference between, making love, having sex, and fucking?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
Nothing too Serious
14- What is an embarrassing moment in your life? How about your most embarrassing?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
70~ Would/do you have/like anal sex?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What is your favorite position? Why?
What was the longest? What was the shortest?
(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…)
53~ How much can you tell me about the one thing you are most passionate about?
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- How often do you drink alcohol? What is your favorite drink?
46~ Have you ever used furniture, or other types of things to aid you while having 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?
51~ What tends to bring a smile to your face?
32- What's your greatest talent? Can I see it right now?
9- What’s your favorite season and why? What’s your least favorite?
34~ Do you like the lights on or off during sex?
62~ Have you used adult toys?
29- How superstitious are you?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
20- What’s your favorite candy? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
Repairman/Lonely Wife Virgin/Experienced
71~ Would you give your partner a hand or foot job? Would you receive one?
2- What’s your favorite color? Do you a least favorite?
52~ What are your hobbies?
31- If given a chance to be immortal, would you take it? Why?
27- What was/ is nickname? Does it have a meaning behind it?
11- How about if they like a certain sports team? 12-How about drinking too much?
3- What Superhero or Superpower would you want to be/have?
9~ How many times over your lifetime do you think you have had sex so far?
Have you ever? Care to Share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Get this wrong and this could mean the end… :-) some funny, some not…
How about if they talk dirty and/or call you names?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
23- What is your dream job? What was it as a child?
17- What’s your favorite holiday? What’s your least favorite?
4- For a pet, Cat, dog or other?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
How many partners have you had oral sex with? Who? Care to Share?