What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 13:03
19- Do/have you smoked? What do you prefer? How often?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
If there was only one man remaining on the Earth, would this be regarded as extinction?
39~ What are your love languages?
15~ Have you ever been “in love”? Who? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Creatine for the brain: How this workout supplement supercharges memory and focus - Times of India
52~ What are your hobbies?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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…
Do you like it when they show and tell you what they want?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Any that are a turn off?
45~ How do you feel about me blindfolding you? How about blindfolding me?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
Would you do it again, and would you rather 2 females or 2 males?
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?
62~ Have you used adult toys?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you watch it? What is your favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
* Give a rating for each one (0-100)
Do you usually wear your panties over or under your pantyhose?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Nothing too Serious
How many times do you think you have “made love”?
How did the Nazis figure out whether a person or community is 'Aryan' or not?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What's the most valuable lesson you've learned in life, and how has it impacted your journey so far?
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,
33- If you could visit any time period, when would you pick? Please explain why?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How do you handle your mother-in-law after you heard her talking badly about you in the next room?
27- What was/ is nickname? Does it have a meaning behind it?
22- Do you have any birth marks? How about scars? Care to share how you got them?
5- Have you ever been hypnotized? Would you allow yourself to be?
Why do our deceased do not protect us from other bad spirits?
*** What’s Your Favorite…? ***
That one or two things that made you go hmmmm, OMG or wow!
If you say it, I will stop, and we can talk about it when you are ready.
What are some cute picnic ideas for a romantic date?
50~ How many children do you have? What are their ages?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
11- How about if they like a certain sports team? 12-How about drinking too much?
What is your favorite position? Why?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
9- If you could have three wishes, what would they be? Why?
You know that I will be 100% truthful, so ask.
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral 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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
44~ Care to share something about yourself that no one else knows about you?
Over time has your thoughts on sex changed?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Will you cheat again? How can, you be sure? Define what cheating is to you.
Family Relation Age Play
83~ How do you feel about Porn?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
70~ Would/do you have/like anal sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
10- List 5 of your top pet peeves.
Nurse/Patient Celebrity/Fan
84~ How do you feel about reading/listening to adult stories?
Repairman/Lonely Wife Virgin/Experienced
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
82~ Do you have any fantasies involving Role-Playing?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
40~ What’s the weirdest place you’ve ever had sex?
26~ What side of the bed do you sleep on?
If yes, what?
13- What’s your favorite drink? What’s your least favorite?
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?
92~ Everyone needs a “safe” word. What is yours?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
30~ What's something unexpected that turns you on?
17- What’s your favorite holiday? What’s your least favorite?
33- Beach or Mountains? Or is there another place to like better?
2- What’s your favorite color? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
51~ Are you willing to play adult games with your partner?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
23- What is your dream job? What was it as a child?
21~ What was the best date you ever went on? What has been the worst?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
28- What are some things that people do that irritate you?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Doctor/Nurse Stripper/Client
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Model/Photographer Police/Criminal
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
3- Should Pluto still be considered a planet? 4- How about smoking?
Escort/Client Job Applicant/Hiring Manager
19~ Who/when was your first “heartbreak”?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
61~ How willing would you be to try new sexual positions?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
49~ How many times have you been married? Why did they end?
13~ Is there a difference between, making love, having sex, and fucking?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
36~ What is your favorite time of day to have sex/make love?
19- What’s your favorite fairytale? What’s your least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
How many partners have you had oral sex with? Who? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
11~ Have you ever been caught by your parents or children or others while having sex?
18- How often do you drink alcohol? What is your favorite drink?
76~ Have you had a threesome? Care to Share?
21- What's your favorite way to spend a weekend or time off?
How about if they talk dirty and/or call you names?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
42~ What’s your biggest regret in life?
Have you ever? Care to Share?
29- How superstitious are you?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
13- What is the craziest/scariest thing you've ever done?
15- What bad habit do you wish you could quit? Do you have any addictions?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
10- What is your favorite family tradition? What’s your least favorite?
17- Have you ever done drugs? Which ones? How often?
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?
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?
Any that are a turn off?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
1- What’s your favorite animal? Do you a least favorite?
1- What was your first impression of me? Has it changed?
4- For a pet, Cat, dog or other?
*** Questions about Relationships/Past ***
Teacher/Student Stranger/One Night Stand
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would you mind if your partner watched it? How about together vs alone?
31- If given a chance to be immortal, would you take it? Why?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What is your favorite toy? Ever wanted to try a specific toy?
Master/Slave Boss/Maid
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What have you learned about yourself that you did not before this?
53~ How much can you tell me about the one thing you are most passionate about?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
9~ How many times over your lifetime do you think you have had sex so far?
11- What's your favorite restaurant? What’s your least favorite?
51~ What tends to bring a smile to your face?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
14- What's your favorite dessert? Do you a least favorite?
34~ Do you like the lights on or off during sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
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…
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
11- List at least 5 things on your bucket list. Have you done any of them already?
48~ Do you have any siblings? Are you close to your family?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
(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…)
If NO, would you ever have one? Would it be with 2 men or 2 women?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
22- What is your favorite childhood memory? What is your least favorite?
If you win, what will you make them do?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Please share Did you stop?
13- How about having a certain hair cut/style?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What have you learned about me that was new and/or surprising?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
29~ What are some things that turn you off? What is your biggest turn off?
Can you Deep Throat? Do you like the taste of yourself?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
67~ Do you like it when your partner moans and/or is vocal during sex?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you think this brought you closer together?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Would you ever want to be woken up with oral and/or intercourse?
What was the longest? What was the shortest?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
89~ Do you like taking showers together?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Prisoner/Prison Guard Landlord/Tenant
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
32- What's your greatest talent? Can I see it right now?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
*** Random Questions ***
25~ How do you feel about PDA? (Public Display of Affection)
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)
Do you have a favorite? Is it ok if your partner does?
3- What’s your favorite smell? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
7- What are your thoughts on religion? Is there an afterlife?
What do you dislike about me? I asked you to be 100% honest.
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Would you read them together?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
34- Ever been to a concert? What was your favorite? Who would you like to see?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
*** Questions About Me ***
1~ How old were you when you had your first kiss? Who? Care to Share?
What is your view on sex? Meaning, When/Where/ How often/
47~ What would be your dream job and why?
9- What’s your favorite season and why? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
What’s the longest time you gone without having sex, after, having it? How much time between the others?
52~ Are you willing to make “those types” of bets with your partner?
How well do you know me? And some of your thoughts about me
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
How old are you? Male or Female?
Do you like the “69” position? Do you prefer to be on top or bottom?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
8- What are your thoughts on politics?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
12- What is the weirdest thing you've ever eaten?
81~ Do you have any kinks and/or fetishes?
18~ Who/when was your first “crush”?
48~ Have you ever paid or been paid for sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3- What Superhero or Superpower would you want to be/have?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
10~ How many dates are necessary before you to have sex with someone?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
7-What do I do in bed that drives you wild? How about, what turns you off?
What would you say to prove to yourself that it was really you?
7- What if a person smells a certain way? 8- How about smoking?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
9- Is there something you’ve always wanted to ask me but you’re afraid?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
65~ Describe the best orgasm you’ve ever had? Care to share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
12- What’s your favorite food? What’s your least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
14- What is an embarrassing moment in your life? How about your most embarrassing?
20- What’s your favorite candy? What’s your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Does the thought excite you? Care to share?
36- Do you play video games? What is your favorite? Do you a least favorite?
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?
*** Deal Breaker Questions ***
92~ Have you ever had or have an STD? How many? What was it?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
I would allow you to do it… What would you do to me?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?