What is the most interesting question you can ask to get to know someone?
Last Updated: 23.06.2025 04:38
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
18- How often do you drink alcohol? What is your favorite drink?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
7- What are your thoughts on religion? Is there an afterlife?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Nothing too Serious
Have you ever been spanked in front of a group of people?
8- What's your favorite flavor of ice cream? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
50~ How many children do you have? What are their ages?
What one thing makes someone a very mature person?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
How about if they talk dirty and/or call you names?
What would be the lowest score with 9 strikes and no gutter balls?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Are fanservice-y characters (i.e. Lara Croft, Tifa Lockhart) immediately bad?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
15~ Have you ever been “in love”? Who? Care to Share?
18~ Who/when was your first “crush”?
What movies have not aged well?
36~ What is your favorite time of day to have sex/make love?
4- For a pet, Cat, dog or other?
12- What is the weirdest thing you've ever eaten?
Phil Mickelson’s U.S. Open career likely ends with final bit of heartbreak - NBC Sports
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
5- Have you ever been hypnotized? Would you allow yourself to be?
Get this wrong and this could mean the end… :-) some funny, some not…
Milky Way arcs over Kitt Peak National Observatory photo of the day for June 16, 2025 - Space
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Can you share a story of someone who had a lucky experience while hitchhiking?
82~ Do you have any fantasies involving Role-Playing?
81~ Do you have any kinks and/or fetishes?
9- If you could have three wishes, what would they be? Why?
9- What’s your favorite season and why? What’s your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
62~ Have you used adult toys?
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53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
You know that I will be 100% truthful, so ask.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Elly De La Cruz throws out Javier Baez with mind-boggling 98 mph throw - New York Post
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
21~ What was the best date you ever went on? What has been the worst?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
What are some sex stories from your college days?
29~ What are some things that turn you off? What is your biggest turn off?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
49~ How many times have you been married? Why did they end?
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?
Do you like it when they show and tell you what they want?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
11- What's your favorite restaurant? What’s your least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Would you read them together?
Would you mind if your partner watched it? How about together vs alone?
13~ Is there a difference between, making love, having sex, and fucking?
* Give a rating for each one (0-100)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
10~ How many dates are necessary before you to have sex with someone?
12- What’s your favorite food? What’s your least 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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
33- If you could visit any time period, when would you pick? Please explain why?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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?
27- What was/ is nickname? Does it have a meaning behind it?
How well do you know me? And some of your thoughts about me
13- How about having a certain hair cut/style?
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?
53~ How much can you tell me about the one thing you are most passionate about?
65~ Describe the best orgasm you’ve ever had? Care to share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
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?
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 win, what will you make them do?
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?
(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…)
How old are you? Male or Female?
60~ How important is oral sex? Do you like receiving? Do you like giving?
34~ Do you like the lights on or off during 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?
Can you Deep Throat? Do you like the taste of yourself?
8- What are your thoughts on politics?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
30~ What's something unexpected that turns you on?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Nurse/Patient Celebrity/Fan
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
19- What’s your favorite fairytale? What’s your least favorite?
Family Relation Age Play
How many partners have you had oral sex with? Who? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
13- What is the craziest/scariest thing you've ever done?
17- Have you ever done drugs? Which ones? How often?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Escort/Client Job Applicant/Hiring Manager
44~ Care to share something about yourself that no one else knows about you?
56~ Would you ever go to a strip club with your partner? Have you ever been? 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…
What’s the longest time you gone without having sex, after, having it? How much time between the others?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
22- What is your favorite childhood memory? What is your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
48~ Have you ever paid or been paid for sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
31- If given a chance to be immortal, would you take it? Why?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
76~ Have you had a threesome? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
37- Do you like your name? If you could change it, what would you change it too?
89~ Do you like taking showers together?
25~ How do you feel about PDA? (Public Display of Affection)
Have you ever? Care to Share?
What have you learned about me that was new and/or surprising?
23- What is your dream job? What was it as a child?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
71~ Would you give your partner a hand or foot job? Would you receive one?
9~ How many times over your lifetime do you think you have had sex so far?
What do you dislike about me? I asked you to be 100% honest.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Prisoner/Prison Guard Landlord/Tenant
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Any that are a turn off?
What is your favorite toy? Ever wanted to try a specific toy?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Do you think this brought you closer together?
The Ice Breaker Questions
If YES, was it with 2 men or 2 women? Did you enjoy it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Would you ever want to be woken up with oral and/or intercourse?
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)
*** Random Questions ***
32- What's your greatest talent? Can I see it right now?
83~ How do you feel about Porn?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Does the thought excite you? Care to share?
1- What was your first impression of me? Has it changed?
28~ What are some things that turn on? What is your biggest turn on?
9- Is there something you’ve always wanted to ask me but you’re afraid?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
39~ What are your love languages?
*** Questions about Relationships/Past ***
What have you learned about yourself that you did not before this?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Master/Slave Boss/Maid
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?
3- Should Pluto still be considered a planet? 4- How about smoking?
20- What’s your favorite candy? What’s your least favorite?
19- Do/have you smoked? What do you prefer? How often?
Do you watch it? What is your favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Over time has your thoughts on sex changed?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
26~ What side of the bed do you sleep on?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
14- What's your favorite dessert? Do you a least favorite?
*** Deal Breaker Questions ***
41~ Are there moments in your past that you would want to change? Please share 3 of them.
10- What is your favorite family tradition? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
52~ Are you willing to make “those types” of bets with your partner?
Doctor/Nurse Stripper/Client
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
33- Beach or Mountains? Or is there another place to like better?
67~ Do you like it when your partner moans and/or is vocal during sex?
42~ What’s your biggest regret in life?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Any that are a turn off?
15- What bad habit do you wish you could quit? Do you have any addictions?
What is your view on sex? Meaning, When/Where/ How often/
Model/Photographer Police/Criminal
3- What’s your favorite smell? Do you a least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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?
48~ Do you have any siblings? Are you close to your family?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you like the “69” position? Do you prefer to be on top or bottom?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
29- How superstitious are you?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
47~ What would be your dream job and why?
How many times do you think you have “made love”?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Please share Did you stop?
10- List 5 of your top pet peeves.
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
52~ What are your hobbies?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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 would you say to prove to yourself that it was really you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
11- List at least 5 things on your bucket list. Have you done any of them already?
34- Ever been to a concert? What was your favorite? Who would you like to see?
92~ Have you ever had or have an STD? How many? What was it?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
51~ Are you willing to play adult games with your partner?
I would allow you to do it… What would you do to me?
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~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
7- What’s your favorite book? Do you have a favorite genre? Do you a 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?
11~ Have you ever been caught by your parents or children or others while having sex?
15- What's your favorite saying? What word or phrase is your least favorite?
61~ How willing would you be to try new sexual positions?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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,
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Repairman/Lonely Wife Virgin/Experienced
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
70~ Would/do you have/like anal sex?
11- How about if they like a certain sports team? 12-How about drinking too much?
Would you do it again, and would you rather 2 females or 2 males?
2- What’s your favorite color? Do you a least favorite?
*** What’s Your Favorite…? ***
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Teacher/Student Stranger/One Night Stand
*** Questions About Me ***
What was the longest? What was the shortest?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
If yes, what?
That one or two things that made you go hmmmm, OMG or wow!
84~ How do you feel about reading/listening to adult stories?
What is your favorite position? Why?
28- What are some things that people do that irritate you?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
13- What’s your favorite drink? What’s your least favorite?
38~ Share your most embarrassing sexual memory?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If you say it, I will stop, and we can talk about it when you are ready.
1- What’s your favorite animal? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
36- Do you play video games? What is your favorite? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
21- What's your favorite way to spend a weekend or time off?
Would /have you ever given your partner a lap dance and Striptease?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
51~ What tends to bring a smile to your face?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
19~ Who/when was your first “heartbreak”?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you have a favorite? Is it ok if your partner does?