What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 05:18
If you win, what will you make them do?
That one or two things that made you go hmmmm, OMG or wow!
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
I have the power to talk to aliens through using telepathy. Why do people think I'm crazy?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Any that are a turn off?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How about if they talk dirty and/or call you names?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
13- How about having a certain hair cut/style?
Any that are a turn off?
14- What is an embarrassing moment in your life? How about your most embarrassing?
*** Deal Breaker Questions ***
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Why do I feel so lazy every time I get into my room?
How old are you? Male or Female?
15- What's your favorite saying? What word or phrase is 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?
How are Hinduism and Sikhism related, considering they both originated in Punjab, India?
Over time has your thoughts on sex changed?
51~ What tends to bring a smile to your face?
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?
Have you ever lied to your family? What were the circumstances?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
45~ How do you feel about me blindfolding you? How about blindfolding me?
67~ Do you like it when your partner moans and/or is vocal during sex?
If you could instantly cancel one social norm, what would it be?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
22- What is your favorite childhood memory? What is your least favorite?
What have you learned about me that was new and/or surprising?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
What would you say to prove to yourself that it was really you?
Can a cop pull you over walking home asking why you are out so late?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
What was it like being spanked as a kid?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
What are some funny and smart quotes?
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?
3- Should Pluto still be considered a planet? 4- How about smoking?
84~ How do you feel about reading/listening to adult stories?
34~ Do you like the lights on or off during sex?
The Ice Breaker Questions
Who is the beast of Revelation 13?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
Would you mind if your partner watched it? How about together vs alone?
28- What are some things that people do that irritate you?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
12- What’s your favorite food? 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?
Model/Photographer Police/Criminal
18- How often do you drink alcohol? What is your favorite drink?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Do you like the “69” position? Do you prefer to be on top or bottom?
Family Relation Age Play
Master/Slave Boss/Maid
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
How many partners have you had oral sex with? Who? Care to Share?
3- What Superhero or Superpower would you want to be/have?
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…
Would you do it again, and would you rather 2 females or 2 males?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
5- Have you ever been hypnotized? Would you allow yourself to be?
I would allow you to do it… What would you do to me?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
19~ Who/when was your first “heartbreak”?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
8- What are your thoughts on politics?
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?
* Give a rating for each one (0-100)
38~ Share your most embarrassing sexual memory?
53~ How much can you tell me about the one thing you are most passionate about?
Repairman/Lonely Wife Virgin/Experienced
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Please share Did you stop?
What is your favorite position? Why?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
3- What’s your favorite smell? Do you a least favorite?
10- List 5 of your top pet peeves.
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?
Do you think this brought you closer together?
26~ What side of the bed do you sleep on?
What do you dislike about me? I asked you to be 100% honest.
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
14- What's your favorite dessert? Do you a least favorite?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
40~ What’s the weirdest place you’ve ever had sex?
What was the longest? What was the shortest?
52~ What are your hobbies?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
If NO, would you ever have one? Would it be with 2 men or 2 women?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
70~ Would/do you have/like anal sex?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
1- What’s your favorite animal? Do you a least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
51~ Are you willing to play adult games with your partner?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
6- Do you have dreams? Can you remember them? What do you usually dream about?
1- What was your first impression of me? Has it changed?
How many times do you think you have “made love”?
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,
Do you have a favorite? Is it ok if your partner does?
9~ How many times over your lifetime do you think you have had sex so far?
Would you allow me to clean every part of your body with my soapy hands and fingers?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
61~ How willing would you be to try new sexual positions?
62~ Have you used adult toys?
What have you learned about yourself that you did not before this?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Would /have you ever given your partner a lap dance and Striptease?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Nothing too Serious
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
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?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
7- What if a person smells a certain way? 8- How about smoking?
25~ How do you feel about PDA? (Public Display of Affection)
*** What’s Your Favorite…? ***
7-What do I do in bed that drives you wild? How about, what turns you off?
17- What’s your favorite holiday? What’s your least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
23- What is your dream job? What was it as a child?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
47~ What would be your dream job and why?
(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…)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
22- Do you have any birth marks? How about scars? Care to share how you got them?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
33- Beach or Mountains? Or is there another place to like better?
39~ What are your love languages?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
17- Have you ever done drugs? Which ones? How often?
83~ How do you feel about Porn?
Escort/Client Job Applicant/Hiring Manager
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Get this wrong and this could mean the end… :-) some funny, some not…
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
52~ Are you willing to make “those types” of bets with your partner?
13~ Is there a difference between, making love, having sex, and fucking?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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?
21~ What was the best date you ever went on? What has been the worst?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
20- What’s your favorite candy? What’s your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
44~ Care to share something about yourself that no one else knows about you?
32- What's your greatest talent? Can I see it right now?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
33- If you could visit any time period, when would you pick? Please explain why?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
48~ Have you ever paid or been paid for sex?
4- For a pet, Cat, dog or other?
30~ What's something unexpected that turns you on?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
*** Questions About Me ***
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
You know that I will be 100% truthful, so ask.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
34- Ever been to a concert? What was your favorite? Who would you like to see?
21- What's your favorite way to spend a weekend or time off?
2- What’s your favorite color? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What is your view on sex? Meaning, When/Where/ How often/
11- What's your favorite restaurant? What’s your least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
19- Do/have you smoked? What do you prefer? How often?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
18~ Who/when was your first “crush”?
Nurse/Patient Celebrity/Fan
If YES, was it with 2 men or 2 women? Did you enjoy it?
36- Do you play video games? What is your favorite? Do you a least favorite?
48~ Do you have any siblings? Are you close to your family?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Does the thought excite you? Care to share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Teacher/Student Stranger/One Night Stand
12- What is the weirdest thing you've ever eaten?
How well do you know me? And some of your thoughts about me
9- What’s your favorite season and why? What’s your least favorite?
*** Questions about Relationships/Past ***
36~ What is your favorite time of day to have sex/make love?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
31- If given a chance to be immortal, would you take it? Why?
Do you like it when they show and tell you what they want?
50~ How many children do you have? What are their ages?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
If yes, what?
19- What’s your favorite fairytale? What’s your least favorite?
9- If you could have three wishes, what would they be? Why?
Would you read them together?
15- What bad habit do you wish you could quit? Do you have any addictions?
29- How superstitious are you?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
28~ What are some things that turn on? What is your biggest turn on?
11- List at least 5 things on your bucket list. Have you done any of them already?
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…
What is your favorite toy? Ever wanted to try a specific toy?
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?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
49~ How many times have you been married? Why did they end?
42~ What’s your biggest regret in life?
Doctor/Nurse Stripper/Client
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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)
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
13- What’s your favorite drink? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
92~ Everyone needs a “safe” word. What is yours?
76~ Have you had a threesome? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
65~ Describe the best orgasm you’ve ever had? Care to share?
92~ Have you ever had or have an STD? How many? What was it?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
11~ Have you ever been caught by your parents or children or others while having sex?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Have you ever? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
7- What are your thoughts on religion? Is there an afterlife?
82~ Do you have any fantasies involving Role-Playing?
Prisoner/Prison Guard Landlord/Tenant
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
10~ How many dates are necessary before you to have sex with someone?
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?
10- What is your favorite family tradition? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
*** Random Questions ***
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 allow me to shave your legs? How about your pubic hair? How about shower sex?
89~ Do you like taking showers together?
27- What was/ is nickname? Does it have a meaning behind it?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Can you Deep Throat? Do you like the taste of yourself?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Do you watch it? What is your favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?