What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 05:17
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Family Relation Age Play
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
What is the best way to get revenge on people who hurt you?
9- What’s your favorite season and why? What’s your least favorite?
12- What’s your favorite food? What’s your least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
48~ Do you have any siblings? Are you close to your family?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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…
19~ Who/when was your first “heartbreak”?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What is the impact of being stereotyped as poor on an individual's life? How does it make them feel?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
76~ Have you had a threesome? Care to Share?
13- What is the craziest/scariest thing you've ever done?
Starbucks moves to the next phase in its turnaround: Winning over employees - CNBC
21~ What was the best date you ever went on? What has been the worst?
Can you Deep Throat? Do you like the taste of yourself?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Exactly When Apple Will Launch iPhone 17 And iPhone 17 Pro - Forbes
What is your favorite position? Why?
Do you have a favorite? Is it ok if your partner does?
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?
Why is my Whirlpool fridge not cooling but the freezer works? What is the solution?
What have you learned about me that was new and/or surprising?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What have you learned about yourself that you did not before this?
Why do people with trauma easily recognize other people with trauma through eye contact?
What is your favorite toy? Ever wanted to try a specific toy?
Will you cheat again? How can, you be sure? Define what cheating is to you.
What’s the longest time you gone without having sex, after, having it? How much time between the others?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Do you remember one day, you put a deep smile on someone's face and made them very happy?
82~ Do you have any fantasies involving Role-Playing?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
52~ Are you willing to make “those types” of bets with your partner?
38~ Share your most embarrassing sexual memory?
22- What is your favorite childhood memory? What is your least favorite?
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…
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Does the thought excite you? 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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Would you ever want to be woken up with oral and/or intercourse?
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?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
48~ Have you ever paid or been paid for sex?
What was the longest? What was the shortest?
Would you read them together?
* Give a rating for each one (0-100)
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
36~ What is your favorite time of day to have sex/make love?
3- What Superhero or Superpower would you want to be/have?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
92~ Have you ever had or have an STD? How many? What was it?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
How well do you know me? And some of your thoughts about me
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
*** Questions about Relationships/Past ***
29- How superstitious are you?
17- What’s your favorite holiday? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
*** Questions About Me ***
I would allow you to do it… What would you do to me?
70~ Would/do you have/like anal sex?
7- What if a person smells a certain way? 8- How about smoking?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
11~ Have you ever been caught by your parents or children or others while having sex?
9- If you could have three wishes, what would they be? Why?
60~ How important is oral sex? Do you like receiving? Do you like giving?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
15- What's your favorite saying? What word or phrase is your least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
3- Should Pluto still be considered a planet? 4- How about smoking?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Would /have you ever given your partner a lap dance and Striptease?
81~ Do you have any kinks and/or fetishes?
10- What is your favorite family tradition? What’s your least favorite?
How old are you? Male or Female?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
1- What was your first impression of me? Has it changed?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Any that are a turn off?
Model/Photographer Police/Criminal
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
You know that I will be 100% truthful, so ask.
What would you say to prove to yourself that it was really you?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
If you say it, I will stop, and we can talk about it when you are ready.
9~ How many times over your lifetime do you think you have had sex so far?
Master/Slave Boss/Maid
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
47~ What would be your dream job and why?
12- What is the weirdest thing you've ever eaten?
Prisoner/Prison Guard Landlord/Tenant
Please share Did you stop?
2- What’s your favorite color? Do you a least favorite?
19- Do/have you smoked? What do you prefer? How often?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
50~ How many children do you have? What are their ages?
Get this wrong and this could mean the end… :-) some funny, some not…
52~ What are your hobbies?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
49~ How many times have you been married? Why did they end?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Would you mind if your partner watched it? How about together vs alone?
8- What are your thoughts on politics?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
8- What's your favorite flavor of ice cream? Do you a least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Would you allow me to clean every part of your body with my soapy hands and fingers?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Have you ever? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
13- How about having a certain hair cut/style?
7- What are your thoughts on religion? Is there an afterlife?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
If yes, what?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
That one or two things that made you go hmmmm, OMG or wow!
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
7-What do I do in bed that drives you wild? How about, what turns you off?
26~ What side of the bed do you sleep on?
33- If you could visit any time period, when would you pick? Please explain why?
62~ Have you used adult toys?
*** Random Questions ***
22- Do you have any birth marks? How about scars? Care to share how you got them?
Doctor/Nurse Stripper/Client
18- How often do you drink alcohol? What is your favorite drink?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
3- What’s your favorite smell? Do you a least favorite?
4- For a pet, Cat, dog or other?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Do you like it when they show and tell you what they want?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
83~ How do you feel about Porn?
The Ice Breaker Questions
If YES, was it with 2 men or 2 women? Did you enjoy it?
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,
29~ What are some things that turn you off? What is your biggest turn off?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Repairman/Lonely Wife Virgin/Experienced
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
How about if they talk dirty and/or call you names?
Any that are a turn off?
61~ How willing would you be to try new sexual positions?
Over time has your thoughts on sex changed?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
1~ How old were you when you had your first kiss? Who? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
If you win, what will you make them do?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
10~ How many dates are necessary before you to have sex with someone?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Do you think this brought you closer together?
6- Do you have dreams? Can you remember them? What do you usually dream about?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
10- List 5 of your top pet peeves.
51~ What tends to bring a smile to your face?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
19- What’s your favorite fairytale? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How many partners have you had oral sex with? Who? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
1- What’s your favorite animal? Do you a least favorite?
84~ How do you feel about reading/listening to adult stories?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
51~ Are you willing to play adult games with your partner?
Nurse/Patient Celebrity/Fan
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
44~ Care to share something about yourself that no one else knows about you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Nothing too Serious
30~ What's something unexpected that turns you on?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
13~ Is there a difference between, making love, having sex, and fucking?
39~ What are your love languages?
67~ Do you like it when your partner moans and/or is vocal during sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
13- What’s your favorite drink? What’s your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Do you like the “69” position? Do you prefer to be on top or bottom?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
42~ What’s your biggest regret in life?
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?
11- How about if they like a certain sports team? 12-How about drinking too much?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
31- If given a chance to be immortal, would you take it? Why?
20- What’s your favorite candy? What’s your least favorite?
How many times do you think you have “made love”?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
15- What bad habit do you wish you could quit? Do you have any addictions?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
11- What's your favorite restaurant? What’s your least favorite?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
53~ How much can you tell me about the one thing you are most passionate about?
17- Have you ever done drugs? Which ones? How often?
Do you watch it? What is your favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
32- What's your greatest talent? Can I see it right now?
5- Have you ever been hypnotized? Would you allow yourself to be?
40~ What’s the weirdest place you’ve ever had sex?
Escort/Client Job Applicant/Hiring Manager
(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…)
Will you kiss after your partner has gone down on you? Swallow or spit semen?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
34~ Do you like the lights on or off during sex?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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)
5~ When you first started having sex, was it what you thought it would be?
21- What's your favorite way to spend a weekend or time off?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Teacher/Student Stranger/One Night Stand
*** What’s Your Favorite…? ***
33- Beach or Mountains? Or is there another place to like better?
27- What was/ is nickname? Does it have a meaning behind it?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
37- Do you like your name? If you could change it, what would you change it too?
92~ Everyone needs a “safe” word. What is yours?
What do you dislike about me? I asked you to be 100% honest.
14- What's your favorite dessert? Do you a least favorite?
*** Deal Breaker Questions ***
71~ Would you give your partner a hand or foot job? Would you receive one?
18~ Who/when was your first “crush”?
28- What are some things that people do that irritate you?
23- What is your dream job? What was it as a child?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What is your view on sex? Meaning, When/Where/ How often/
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
89~ Do you like taking showers together?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?