What is the most interesting question you can ask to get to know someone?
Last Updated: 03.07.2025 00:44
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
What is a promotion strategy in marketing?
7~ How many times in one day have you had sex? Who/When/Where? 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…
Model/Photographer Police/Criminal
Mario Kart World is the perfect Switch 2 launch game - The Verge
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
(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…)
Steelers TE wants no part of Jonnu Smith trade - Behind the Steel Curtain
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
51~ What tends to bring a smile to your face?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
The #1 Underrated Vegetable with More Vitamin C Than an Orange, According to Dietitians - EatingWell
Teacher/Student Stranger/One Night Stand
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
50~ How many children do you have? What are their ages?
Climate Disasters Hit the Brain Before Babies Are Even Born, Study Suggests - Gizmodo
Nurse/Patient Celebrity/Fan
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
1- What’s your favorite animal? Do you a least favorite?
89~ Do you like taking showers together?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
If you win, what will you make them do?
How did Kate Mulgrew feel about Jeri Ryan joining the cast of Star Trek: Voyager?
1- What was your first impression of me? Has it changed?
How about if they talk dirty and/or call you names?
15- What's your favorite saying? What word or phrase is your least favorite?
Princess Peach's Voice Actor Has Been Replaced After 18 Years - Nintendo Life
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
1~ How old were you when you had your first kiss? Who? Care to Share?
42~ What’s your biggest regret in life?
What's the most valuable lesson you've learned in life, and how has it impacted your journey so far?
92~ Have you ever had or have an STD? How many? What was it?
11~ Have you ever been caught by your parents or children or others while having sex?
Do you watch it? What is your favorite?
Google Play Store replaces ‘1-tap buy’ with ‘Slide to buy’ - 9to5Google
Any that are a turn off?
92~ Everyone needs a “safe” word. What is yours?
Do you like the “69” position? Do you prefer to be on top or bottom?
What is your favorite position? Why?
Escort/Client Job Applicant/Hiring Manager
19- Do/have you smoked? What do you prefer? How often?
30~ What's something unexpected that turns you on?
Have you ever? 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?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
33- If you could visit any time period, when would you pick? Please explain why?
22- What is your favorite childhood memory? What is your least favorite?
44~ Care to share something about yourself that no one else knows about you?
14- What is an embarrassing moment in your life? How about your most embarrassing?
26~ What side of the bed do you sleep on?
13- What’s your favorite drink? What’s your least favorite?
83~ How do you feel about Porn?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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,
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
4- For a pet, Cat, dog or other?
What is your view on sex? Meaning, When/Where/ How often/
If YES, was it with 2 men or 2 women? Did you enjoy it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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?
18~ Who/when was your first “crush”?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
15~ Have you ever been “in love”? Who? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
Would you mind if your partner watched it? How about together vs alone?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
45~ How do you feel about me blindfolding you? How about blindfolding me?
9- Is there something you’ve always wanted to ask me but you’re afraid?
36~ What is your favorite time of day to have sex/make love?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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?
82~ Do you have any fantasies involving Role-Playing?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
32- What's your greatest talent? Can I see it right now?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
What do you dislike about me? I asked you to be 100% honest.
33- Beach or Mountains? Or is there another place to like better?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
21- What's your favorite way to spend a weekend or time off?
Can you Deep Throat? Do you like the taste of yourself?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Do you have a favorite? Is it ok if your partner does?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
How old are you? Male or Female?
13~ Is there a difference between, making love, having sex, and fucking?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
12- What’s your favorite food? What’s your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
8- What's your favorite flavor of ice cream? Do you a least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
38~ Share your most embarrassing sexual memory?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
34~ Do you like the lights on or off during sex?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
39~ What are your love languages?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
8- What are your thoughts on politics?
Get this wrong and this could mean the end… :-) some funny, some not…
Please share Did you stop?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
6- Do you have dreams? Can you remember them? What do you usually dream about?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
5~ When you first started having sex, was it what you thought it would be?
17- Have you ever done drugs? Which ones? How often?
What have you learned about me that was new and/or surprising?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
23- What is your dream job? What was it as a child?
Over time has your thoughts on sex changed?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
71~ Would you give your partner a hand or foot job? Would you receive one?
37- Do you like your name? If you could change it, what would you change it too?
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 have you learned about yourself that you did not before this?
Would /have you ever given your partner a lap dance and Striptease?
48~ Have you ever paid or been paid for sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
*** What’s Your Favorite…? ***
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
15- What bad habit do you wish you could quit? Do you have any addictions?
48~ Do you have any siblings? Are you close to your family?
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?
10- What is your favorite family tradition? What’s your least favorite?
18- How often do you drink alcohol? What is your favorite drink?
Doctor/Nurse Stripper/Client
40~ What’s the weirdest place you’ve ever had sex?
7- What if a person smells a certain way? 8- How about smoking?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
I would allow you to do it… What would you do to me?
9- What’s your favorite season and why? What’s your least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
Do you like it when they show and tell you what they want?
*** Deal Breaker Questions ***
67~ Do you like it when your partner moans and/or is vocal during sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
14- What's your favorite dessert? Do you a least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
* Give a rating for each one (0-100)
*** Random Questions ***
Do you shave/trim your pubic hair? For you guys do you shave your balls?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
28- What are some things that people do that irritate you?
Prisoner/Prison Guard Landlord/Tenant
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…
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?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
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?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
If NO, would you ever have one? Would it be with 2 men or 2 women?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
76~ Have you had a threesome? Care to Share?
10- List 5 of your top pet peeves.
80~ Share your top three fantasies/desires. (Be detailed) 😊
47~ What would be your dream job and why?
19~ Who/when was your first “heartbreak”?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How many partners have you had oral sex with? Who? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
25~ How do you feel about PDA? (Public Display of Affection)
Do you think this brought you closer together?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
29- How superstitious are you?
What is your favorite toy? Ever wanted to try a specific toy?
Would you do it again, and would you rather 2 females or 2 males?
Does the thought excite you? Care to share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
11- How about if they like a certain sports team? 12-How about drinking too much?
If yes, what?
52~ What are your hobbies?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
How well do you know me? And some of your thoughts about me
Repairman/Lonely Wife Virgin/Experienced
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
*** Questions about Relationships/Past ***
Will you cheat again? How can, you be sure? Define what cheating is to you.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
*** Questions About Me ***
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
7-What do I do in bed that drives you wild? How about, what turns you off?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
You know that I will be 100% truthful, so ask.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
28~ What are some things that turn on? What is your biggest turn on?
How many times do you think you have “made love”?
78~ Have you ever thought about making out or having sex with someone of the same sex? 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?
Would you read them together?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
52~ Are you willing to make “those types” of bets with your partner?
The Ice Breaker Questions
81~ Do you have any kinks and/or fetishes?
61~ How willing would you be to try new sexual positions?
Master/Slave Boss/Maid
Any that are a turn off?
7- What are your thoughts on religion? Is there an afterlife?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
11- What's your favorite restaurant? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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?
27- What was/ is nickname? Does it have a meaning behind it?
31- If given a chance to be immortal, would you take it? Why?
9- If you could have three wishes, what would they be? Why?
13- How about having a certain hair cut/style?
60~ How important is oral sex? Do you like receiving? Do you like giving?
9~ How many times over your lifetime do you think you have had sex so far?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
20- What’s your favorite candy? What’s your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
12- What is the weirdest thing you've ever eaten?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
3- What’s your favorite smell? Do you a least favorite?
Would you ever want to be woken up with oral and/or intercourse?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
3- Should Pluto still be considered a planet? 4- How about smoking?
What was the longest? What was the shortest?
70~ Would/do you have/like anal sex?
That one or two things that made you go hmmmm, OMG or wow!
3- What Superhero or Superpower would you want to be/have?
What would you say to prove to yourself that it was really you?
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?
2- What’s your favorite color? Do you a least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Nothing too Serious
22- Do you have any birth marks? How about scars? Care to share how you got them?
13- What is the craziest/scariest thing you've ever done?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
49~ How many times have you been married? Why did they end?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
62~ Have you used adult toys?
84~ How do you feel about reading/listening to adult stories?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
5- Have you ever been hypnotized? Would you allow yourself to be?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
10~ How many dates are necessary before you to have sex with someone?
Family Relation Age Play
17- What’s your favorite holiday? What’s your least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)