What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 01:50
13- What is the craziest/scariest thing you've ever done?
I would allow you to do it… What would you do to me?
19- What’s your favorite fairytale? What’s your least favorite?
1- What’s your favorite animal? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Why am I not attracted to masculine men? Why do I like more feminine attributes on a man?
What have you learned about yourself that you did not before this?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
51~ What tends to bring a smile to your face?
Why do people stay in cults after they have joined?
*** Deal Breaker Questions ***
22- Do you have any birth marks? How about scars? Care to share how you got them?
Prisoner/Prison Guard Landlord/Tenant
38~ Share your most embarrassing sexual memory?
92~ Everyone needs a “safe” word. What is yours?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How many partners have you had oral sex with? Who? Care to Share?
26~ What side of the bed do you sleep on?
Do married men know when their wives are having affairs?
30~ What's something unexpected that turns you on?
53~ How much can you tell me about the one thing you are most passionate about?
50~ How many children do you have? What are their ages?
When was the first time you suck on a penis?
1- What was your first impression of me? Has it changed?
39~ What are your love languages?
3- What’s your favorite smell? Do you a least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
45~ How do you feel about me blindfolding you? How about blindfolding me?
84~ How do you feel about reading/listening to adult stories?
How does it feel to watch your wife get fucked hard?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
10- What is your favorite family tradition? What’s your least favorite?
How would you feel if your girlfriend had dick pics on her phone?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
What is your favorite toy? Ever wanted to try a specific toy?
83~ How do you feel about Porn?
Why do men say women hit the wall at 24?
Nothing too Serious
11- What's your favorite restaurant? What’s your least favorite?
How many times do you think you have “made love”?
Person with measles visited Boston hotel, museum, airport, health officials warn - NBC Boston
23- What is your dream job? What was it as a child?
27- What was/ is nickname? Does it have a meaning behind it?
You know that I will be 100% truthful, so ask.
17- Have you ever done drugs? Which ones? How often?
33- Beach or Mountains? Or is there another place to like better?
10~ How many dates are necessary before you to have sex with someone?
15~ Have you ever been “in love”? Who? Care to Share?
Any that are a turn off?
Would you do it again, and would you rather 2 females or 2 males?
14- What is an embarrassing moment in your life? How about your most embarrassing?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
12- What’s your favorite food? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Have you ever? Care to Share?
Does the thought excite you? Care to share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Please share Did you stop?
29- How superstitious are you?
52~ What are your hobbies?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral 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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
What would you say to prove to yourself that it was really you?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
19~ Who/when was your first “heartbreak”?
5~ When you first started having sex, was it what you thought it would be?
Would you mind if your partner watched it? How about together vs alone?
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?
Family Relation Age Play
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
32- What's your greatest talent? Can I see it right now?
15- What's your favorite saying? What word or phrase is your least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
12- What is the weirdest thing you've ever eaten?
31- If given a chance to be immortal, would you take it? Why?
9~ How many times over your lifetime do you think you have had sex so far?
7- What if a person smells a certain way? 8- How about smoking?
49~ How many times have you been married? Why did they end?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched 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.
71~ Would you give your partner a hand or foot job? Would you receive one?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Do you like it when they show and tell you what they want?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Doctor/Nurse Stripper/Client
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
48~ Have you ever paid or been paid for sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
13~ Is there a difference between, making love, having sex, and fucking?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
21- What's your favorite way to spend a weekend or time off?
28~ What are some things that turn on? What is your biggest turn on?
21~ What was the best date you ever went on? What has been the worst?
2- What’s your favorite color? Do you a least favorite?
* Give a rating for each one (0-100)
Nurse/Patient Celebrity/Fan
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
48~ Do you have any siblings? Are you close to your family?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
29~ What are some things that turn you off? What is your biggest turn off?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
3- What Superhero or Superpower would you want to be/have?
What was the longest? What was the shortest?
Would you ever want to be woken up with oral and/or intercourse?
36- Do you play video games? What is your favorite? Do you a least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
47~ What would be your dream job and why?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
*** Questions about Relationships/Past ***
25~ How do you feel about PDA? (Public Display of Affection)
17- What’s your favorite holiday? What’s your least favorite?
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?
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)
What do you dislike about me? I asked you to be 100% honest.
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?
65~ Describe the best orgasm you’ve ever had? Care to share?
Do you like the “69” position? Do you prefer to be on top or bottom?
Get this wrong and this could mean the end… :-) some funny, some not…
19- Do/have you smoked? What do you prefer? How often?
Model/Photographer Police/Criminal
4- For a pet, Cat, dog or other?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
20- What’s your favorite candy? What’s your least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
42~ What’s your biggest regret in life?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
18- How often do you drink alcohol? What is your favorite drink?
9- If you could have three wishes, what would they be? Why?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
44~ Care to share something about yourself that no one else knows about you?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
If YES, was it with 2 men or 2 women? Did you enjoy it?
*** Questions About Me ***
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
51~ Are you willing to play adult games with your partner?
What have you learned about me that was new and/or surprising?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
Do you think this brought you closer together?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
13- What’s your favorite drink? What’s your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
What is your view on sex? Meaning, When/Where/ How often/
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?
How old are you? Male or Female?
37- Do you like your name? If you could change it, what would you change it too?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Do you watch it? What is your favorite?
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?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
60~ How important is oral sex? Do you like receiving? Do you like giving?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
92~ Have you ever had or have an STD? How many? What was it?
14- What's your favorite dessert? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
33- If you could visit any time period, when would you pick? Please explain why?
*** What’s Your Favorite…? ***
61~ How willing would you be to try new sexual positions?
*** Random Questions ***
Any that are a turn off?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
40~ What’s the weirdest place you’ve ever had 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…
What is your favorite position? Why?
76~ Have you had a threesome? Care to Share?
34~ Do you like the lights on or off during sex?
9- What’s your favorite season and why? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
11- List at least 5 things on your bucket list. Have you done any of them already?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
If you win, what will you make them do?
Escort/Client Job Applicant/Hiring Manager
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
If you say it, I will stop, and we can talk about it when you are ready.
82~ Do you have any fantasies involving Role-Playing?
8- What are your thoughts on politics?
Over time has your thoughts on sex changed?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
Would /have you ever given your partner a lap dance and Striptease?
22- What is your favorite childhood memory? What is your least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Teacher/Student Stranger/One Night Stand
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would you read them together?
10- List 5 of your top pet peeves.
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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,
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
89~ Do you like taking showers together?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
(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…)
Master/Slave Boss/Maid
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
1~ How old were you when you had your first kiss? Who? Care to Share?
28- What are some things that people do that irritate you?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
9- Is there something you’ve always wanted to ask me but you’re afraid?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
How about if they talk dirty and/or call you names?
18~ Who/when was your first “crush”?
7-What do I do in bed that drives you wild? How about, what turns you off?
8- What's your favorite flavor of ice cream? Do you a least favorite?
81~ Do you have any kinks and/or fetishes?
70~ Would/do you have/like anal sex?
How well do you know me? And some of your thoughts about me
52~ Are you willing to make “those types” of bets with your partner?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
62~ Have you used adult toys?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3- Should Pluto still be considered a planet? 4- How about smoking?
If yes, what?
7- What are your thoughts on religion? Is there an afterlife?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Repairman/Lonely Wife Virgin/Experienced
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
64~ When was your very first orgasm? When was your first from having sex? Care to share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
13- How about having a certain hair cut/style?
That one or two things that made you go hmmmm, OMG or wow!
15- What bad habit do you wish you could quit? Do you have any addictions?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
The Ice Breaker Questions
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?