What is the most interesting question you can ask to get to know someone?
Last Updated: 23.06.2025 08:29
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
*** Deal Breaker Questions ***
9- If you could have three wishes, what would they be? Why?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
33- If you could visit any time period, when would you pick? Please explain why?
How do I run away? I'm 15 and live in Oklahoma.
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Do you have a favorite? Is it ok if your partner does?
8- What's your favorite flavor of ice cream? Do you a least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
3- What’s your favorite smell? Do you a least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
The man who refused to die, and came back from his death 6 times - Times of India
44~ Care to share something about yourself that no one else knows about you?
22- What is your favorite childhood memory? What is your least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
This May Be the Right Time to Raid Your Silver Drawer - Newser
9~ How many times over your lifetime do you think you have had sex so far?
Model/Photographer Police/Criminal
Would /have you ever given your partner a lap dance and Striptease?
What happens when you get sick in a country with universal healthcare? What's the process like?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
32- What's your greatest talent? Can I see it right now?
United-JetBlue Tie Up Leaves American Airlines Bloodied - Live and Let's Fly
Do you like the “69” position? Do you prefer to be on top or bottom?
19~ Who/when was your first “heartbreak”?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Which country has the best and strictest legal system in the world?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
36~ What is your favorite time of day to have sex/make love?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Why don't I want to talk to my girlfriend when she loves me a lot? I feel bored.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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?
U.S. Home Sellers Are Sitting on Nearly $700 Billion Worth of Listings, an All-Time High - Redfin
13- What’s your favorite drink? What’s your least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
2- What’s your favorite color? Do you a least favorite?
D.C. Defenders win UFL title, 58-34 - NBC Sports
If you say it, I will stop, and we can talk about it when you are ready.
18~ Who/when was your first “crush”?
36- Do you play video games? What is your favorite? Do you a least favorite?
What do you do to make yourself sleep early?
21~ What was the best date you ever went on? What has been the worst?
10- List 5 of your top pet peeves.
60~ How important is oral sex? Do you like receiving? Do you like giving?
Who are the most underrated and under-appreciated Hollywood actors/actresses?
11~ Have you ever been caught by your parents or children or others while having sex?
49~ How many times have you been married? Why did they end?
89~ Do you like taking showers together?
O'Malley's dad 'super relaxed' cornering title bout - ESPN
62~ Have you used adult toys?
17- Have you ever done drugs? Which ones? How often?
51~ Are you willing to play adult games with your partner?
If NO, would you ever have one? Would it be with 2 men or 2 women?
How about if they talk dirty and/or call you names?
10- What is your favorite family tradition? What’s your least favorite?
10~ How many dates are necessary before you to have sex with someone?
How many partners have you had oral sex with? Who? Care to Share?
What have you learned about me that was new and/or surprising?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
92~ Everyone needs a “safe” word. What is yours?
17- What’s your favorite holiday? 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?
The Ice Breaker Questions
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
28- What are some things that people do that irritate you?
Would you do it again, and would you rather 2 females or 2 males?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
39~ What are your love languages?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
(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…)
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
13- How about having a certain hair cut/style?
If yes, what?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
4- For a pet, Cat, dog or other?
How many times do you think you have “made love”?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
47~ What would be your dream job and why?
15~ Have you ever been “in love”? Who? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What is your favorite toy? Ever wanted to try a specific toy?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
84~ How do you feel about reading/listening to adult stories?
3- What Superhero or Superpower would you want to be/have?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
6- Do you have dreams? Can you remember them? What do you usually dream about?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
14- What is an embarrassing moment in your life? How about your most embarrassing?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
20- What’s your favorite candy? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
3- Should Pluto still be considered a planet? 4- How about smoking?
19- What’s your favorite fairytale? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
Can you Deep Throat? Do you like the taste of yourself?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- What’s your favorite season and why? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
83~ How do you feel about Porn?
Would you ever want to be woken up with oral and/or intercourse?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
28~ What are some things that turn on? What is your biggest turn on?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
12- What is the weirdest thing you've ever eaten?
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?
Repairman/Lonely Wife Virgin/Experienced
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
21- What's your favorite way to spend a weekend or time off?
12- What’s your favorite food? What’s your least favorite?
8- What are your thoughts on politics?
What do you dislike about me? I asked you to be 100% honest.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
Doctor/Nurse Stripper/Client
38~ Share your most embarrassing sexual memory?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
That one or two things that made you go hmmmm, OMG or wow!
7- What if a person smells a certain way? 8- How about smoking?
42~ What’s your biggest regret in life?
5- Have you ever been hypnotized? Would you allow yourself to be?
*** Random Questions ***
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?
1~ How old were you when you had your first kiss? Who? Care to Share?
Do you like it when they show and tell you what they want?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Nothing too Serious
70~ Would/do you have/like anal sex?
51~ What tends to bring a smile to your face?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
*** What’s Your Favorite…? ***
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
What is your view on sex? Meaning, When/Where/ How often/
1- What’s your favorite animal? Do you a least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
How well do you know me? And some of your thoughts about me
If you win, what will you make them do?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
11- What's your favorite restaurant? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
* Give a rating for each one (0-100)
34~ Do you like the lights on or off during sex?
14- What's your favorite dessert? Do you a least favorite?
76~ Have you had a threesome? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Teacher/Student Stranger/One Night Stand
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Please share Did you stop?
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)
9- Is there something you’ve always wanted to ask me but you’re afraid?
7- What are your thoughts on religion? Is there an afterlife?
What was the longest? What was the shortest?
15- What bad habit do you wish you could quit? Do you have any addictions?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
92~ Have you ever had or have an STD? How many? What was it?
13~ Is there a difference between, making love, having sex, and fucking?
Family Relation Age Play
Do you think this brought you closer together?
29~ What are some things that turn you off? What is your biggest turn off?
Prisoner/Prison Guard Landlord/Tenant
67~ Do you like it when your partner moans and/or is vocal during sex?
Over time has your thoughts on sex changed?
31- If given a chance to be immortal, would you take it? Why?
19- Do/have you smoked? What do you prefer? How often?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
16~ Do you believe in “soulmates”? Have you found yours? Who? 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,
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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…
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
53~ How much can you tell me about the one thing you are most passionate about?
Any that are a turn off?
Do you watch it? What is your favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Would you read them together?
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?
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?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
30~ What's something unexpected that turns you on?
Nurse/Patient Celebrity/Fan
48~ Have you ever paid or been paid for sex?
65~ Describe the best orgasm you’ve ever had? Care to share?
48~ Do you have any siblings? Are you close to your family?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
*** Questions about Relationships/Past ***
71~ Would you give your partner a hand or foot job? Would you receive one?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Get this wrong and this could mean the end… :-) some funny, some not…
If YES, was it with 2 men or 2 women? Did you enjoy it?
What is your favorite position? Why?
61~ How willing would you be to try new sexual positions?
You know that I will be 100% truthful, so ask.
11- List at least 5 things on your bucket list. Have you done any of them already?
1- What was your first impression of me? Has it changed?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
*** Questions About Me ***
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Would you mind if your partner watched it? How about together vs alone?
How old are you? Male or Female?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
11- How about if they like a certain sports team? 12-How about drinking too much?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
23- What is your dream job? What was it as a child?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
26~ What side of the bed do you sleep on?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Escort/Client Job Applicant/Hiring Manager
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
27- What was/ is nickname? Does it have a meaning behind it?
(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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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…
46~ Have you ever used furniture, or other types of things to aid you while having sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
25~ How do you feel about PDA? (Public Display of Affection)
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
33- Beach or Mountains? Or is there another place to like better?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
29- How superstitious are you?
81~ Do you have any kinks and/or fetishes?
Any that are a turn off?
40~ What’s the weirdest place you’ve ever had sex?
52~ What are your hobbies?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
I would allow you to do it… What would you do to me?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Have you ever? Care to Share?
What have you learned about yourself that you did not before this?
Master/Slave Boss/Maid
15- What's your favorite saying? What word or phrase is your least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?