What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 02:47
5~ When you first started having sex, was it what you thought it would be?
Any that are a turn off?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
How do you view men and women who cheat?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
(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…)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Why does a narcissist act like it's nothing when they hurt you?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Unfortunately For Some, These iPhone & iPad Models Won't Be Getting iOS 26 - SlashGear
70~ Would/do you have/like anal sex?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
1~ How old were you when you had your first kiss? Who? Care to Share?
What is the Abu Shusha massacre in Palestine?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Prisoner/Prison Guard Landlord/Tenant
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
If yes, what?
7- What if a person smells a certain way? 8- How about smoking?
Family Relation Age Play
What can I say to a scammer who thinks he loves me, but I don't want to be scammed?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What should you answer when someone says to you in French, "au plaisir de vous revoir"?
9- What’s your favorite season and why? What’s your least favorite?
What have you learned about me that was new and/or surprising?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
What does it mean when you dream that your mother died?
19- Do/have you smoked? What do you prefer? How often?
34- Ever been to a concert? What was your favorite? Who would you like to see?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Why do I sweat between my legs all the time, top off my legs, all way down?
Escort/Client Job Applicant/Hiring Manager
52~ What are your hobbies?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
How do I rat my boss out for serial cheating on his wife?
14- What's your favorite dessert? Do you a least favorite?
29- How superstitious are you?
48~ Have you ever paid or been paid for sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would /have you ever given your partner a lap dance and Striptease?
Model/Photographer Police/Criminal
Does the thought excite you? Care to share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
1- What’s your favorite animal? 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)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
42~ What’s your biggest regret in life?
4- For a pet, Cat, dog or other?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
I would allow you to do it… What would you do to me?
49~ How many times have you been married? Why did they end?
How about if they talk dirty and/or call you names?
48~ Do you have any siblings? Are you close to your family?
52~ Are you willing to make “those types” of bets with your partner?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
12- What’s your favorite food? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
14- What is an embarrassing moment in your life? How about your most embarrassing?
21- What's your favorite way to spend a weekend or time off?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Do you like it when they show and tell you what they want?
Would you allow me to clean every part of your body with my soapy hands and fingers?
7-What do I do in bed that drives you wild? How about, what turns you off?
36- Do you play video games? What is your favorite? Do you a least favorite?
What is your favorite position? Why?
Would you read them together?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
3- What Superhero or Superpower would you want to be/have?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
19- What’s your favorite fairytale? What’s your least favorite?
*** Deal Breaker Questions ***
15- What's your favorite saying? What word or phrase is your least favorite?
* Give a rating for each one (0-100)
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
32- What's your greatest talent? Can I see it right now?
17- Have you ever done drugs? Which ones? How often?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
51~ What tends to bring a smile to your face?
*** Questions About Me ***
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
11- List at least 5 things on your bucket list. Have you done any of them already?
34~ Do you like the lights on or off during sex?
Repairman/Lonely Wife Virgin/Experienced
35- Do you like playing board or cards game? What is your favorite? 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?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
How many times do you think you have “made love”?
67~ Do you like it when your partner moans and/or is vocal during sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
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?
92~ Have you ever had or have an STD? How many? What was it?
*** Questions about Relationships/Past ***
3- What’s your favorite smell? Do you a least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What was the longest? What was the shortest?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
You know that I will be 100% truthful, so ask.
How old are you? Male or Female?
9- If you could have three wishes, what would they be? Why?
What do you dislike about me? I asked you to be 100% honest.
82~ Do you have any fantasies involving Role-Playing?
Any that are a turn off?
13- What is the craziest/scariest thing you've ever done?
36~ What is your favorite time of day to have sex/make love?
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
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
23- What is your dream job? What was it as a child?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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?
2- What’s your favorite color? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
5- Have you ever been hypnotized? Would you allow yourself to be?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
17- What’s your favorite holiday? What’s your least favorite?
26~ What side of the bed do you sleep on?
22- What is your favorite childhood memory? What is your least favorite?
62~ Have you used adult toys?
38~ Share your most embarrassing sexual memory?
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?
39~ What are your love languages?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
If you win, what will you make them do?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Can you Deep Throat? Do you like the taste of yourself?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
11- What's your favorite restaurant? What’s your least favorite?
1- What was your first impression of me? Has it changed?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
That one or two things that made you go hmmmm, OMG or wow!
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
10~ How many dates are necessary before you to have sex with someone?
If you say it, I will stop, and we can talk about it when you are ready.
10- List 5 of your top pet peeves.
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Teacher/Student Stranger/One Night Stand
19~ Who/when was your first “heartbreak”?
31- If given a chance to be immortal, would you take it? Why?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Doctor/Nurse Stripper/Client
18- How often do you drink alcohol? What is your favorite drink?
21~ What was the best date you ever went on? What has been the worst?
53~ How much can you tell me about the one thing you are most passionate about?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What have you learned about yourself that you did not before this?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Is there a smell that most people do not like that you do? Is there a smell 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?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? 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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
9- Is there something you’ve always wanted to ask me but you’re afraid?
11~ Have you ever been caught by your parents or children or others while having sex?
Get this wrong and this could mean the end… :-) some funny, some not…
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
13- How about having a certain hair cut/style?
33- Beach or Mountains? Or is there another place to like better?
10- What is your favorite family tradition? What’s your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
20- What’s your favorite candy? What’s your least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Would you mind if your partner watched it? How about together vs alone?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Nothing too Serious
45~ How do you feel about me blindfolding you? How about blindfolding me?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? 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?
*** Random Questions ***
76~ Have you had a threesome? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
50~ How many children do you have? What are their ages?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
18~ Who/when was your first “crush”?
Please share Did you stop?
28~ What are some things that turn on? What is your biggest turn on?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
15~ Have you ever been “in love”? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
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 have a favorite? Is it ok if your partner does?
What is your view on sex? Meaning, When/Where/ How often/
7- What are your thoughts on religion? Is there an afterlife?
84~ How do you feel about reading/listening to adult stories?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
15- What bad habit do you wish you could quit? Do you have any addictions?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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,
Nurse/Patient Celebrity/Fan
9~ How many times over your lifetime do you think you have had sex so far?
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Do you think this brought you closer together?
37- Do you like your name? If you could change it, what would you change it too?
How many partners have you had oral sex with? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
8- What are your thoughts on politics?
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?
47~ What would be your dream job and why?
13~ Is there a difference between, making love, having sex, and fucking?
44~ Care to share something about yourself that no one else knows about you?
81~ Do you have any kinks and/or fetishes?
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
74~ Have you ever had sex while others watched? Have you ever watched others have 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…
12- What is the weirdest thing you've ever eaten?
30~ What's something unexpected that turns you on?
Do you watch it? What is your favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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…
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
*** What’s Your Favorite…? ***
33- If you could visit any time period, when would you pick? Please explain why?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Would you ever want to be woken up with oral and/or intercourse?
8- What's your favorite flavor of ice cream? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Over time has your thoughts on sex changed?
92~ Everyone needs a “safe” word. What is yours?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
The Ice Breaker Questions
80~ Share your top three fantasies/desires. (Be detailed) 😊
Will you kiss after your partner has gone down on you? Swallow or spit semen?
83~ How do you feel about Porn?
Will you cheat again? How can, you be sure? Define what cheating is to you.
89~ Do you like taking showers together?
Have you ever? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Master/Slave Boss/Maid
40~ What’s the weirdest place you’ve ever had sex?
60~ How important is oral sex? Do you like receiving? Do you like giving?
65~ Describe the best orgasm you’ve ever had? Care to share?
Would you do it again, and would you rather 2 females or 2 males?
3- Should Pluto still be considered a planet? 4- How about smoking?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
11- How about if they like a certain sports team? 12-How about drinking too much?
61~ How willing would you be to try new sexual positions?