What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 03:31
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
7- What are your thoughts on religion? Is there an afterlife?
9- If you could have three wishes, what would they be? Why?
United States roster at 2026 Olympics will differ from 4 Nations Face-Off, GM says - NHL.com
Have you ever? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
83~ How do you feel about Porn?
Do women like men who have slept with many women?
92~ Have you ever had or have an STD? How many? What was it?
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)?
What was the longest? What was the shortest?
1- What’s your favorite animal? Do you a least favorite?
14- What's your favorite dessert? Do you a least favorite?
How do you know how physically attractive you actually are?
14- What is an embarrassing moment in your life? How about your most embarrassing?
81~ Do you have any kinks and/or fetishes?
11- List at least 5 things on your bucket list. Have you done any of them already?
How can someone in your family purposely try to destroy your reputation?
37- Do you like your name? If you could change it, what would you change it too?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
9~ How many times over your lifetime do you think you have had sex so far?
Do flat Earthers really exist? Why do they believe the Earth is flat?
What have you learned about yourself that you did not before this?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
13- What’s your favorite drink? What’s your least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
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7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
25~ How do you feel about PDA? (Public Display of Affection)
13~ Is there a difference between, making love, having sex, and fucking?
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?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Why is my ex still keeping in touch with me even though she dumped me?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
36~ What is your favorite time of day to have sex/make love?
5- Have you ever been hypnotized? Would you allow yourself to be?
*** Questions about Relationships/Past ***
18~ Who/when was your first “crush”?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
11- What's your favorite restaurant? What’s your least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Do you want to have an XXX chat?
19- What’s your favorite fairytale? What’s your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
17- Have you ever done drugs? Which ones? How often?
What’s the weirdest phone call you have ever received?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
22- Do you have any birth marks? How about scars? Care to share how you got them?
* Give a rating for each one (0-100)
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?
8- What's your favorite flavor of ice cream? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
48~ Have you ever paid or been paid for sex?
36- Do you play video games? What is your favorite? Do you a least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
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?
76~ Have you had a threesome? Care to Share?
13- What is the craziest/scariest thing you've ever done?
52~ What are your hobbies?
28~ What are some things that turn on? What is your biggest turn on?
What is your view on sex? Meaning, When/Where/ How often/
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
28- What are some things that people do that irritate you?
62~ Have you used adult toys?
84~ How do you feel about reading/listening to adult stories?
33- If you could visit any time period, when would you pick? Please explain why?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
*** Random Questions ***
20- What’s your favorite candy? What’s your least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
How well do you know me? And some of your thoughts about me
6- Do you have dreams? Can you remember them? What do you usually dream about?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
40~ What’s the weirdest place you’ve ever had sex?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
17- What’s your favorite holiday? What’s your least favorite?
61~ How willing would you be to try new sexual positions?
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,
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Nurse/Patient Celebrity/Fan
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
80~ Share your top three fantasies/desires. (Be detailed) 😊
49~ How many times have you been married? Why did they end?
Would you mind if your partner watched it? How about together vs alone?
3- Should Pluto still be considered a planet? 4- How about smoking?
13- How about having a certain hair cut/style?
60~ How important is oral sex? Do you like receiving? Do you like giving?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Do you think this brought you closer together?
Teacher/Student Stranger/One Night Stand
Would you read them together?
Please share Did you stop?
Get this wrong and this could mean the end… :-) some funny, some not…
9- What’s your favorite season and why? What’s your least favorite?
Do you have a favorite? Is it ok if your partner does?
15- What bad habit do you wish you could quit? Do you have any addictions?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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)
50~ How many children do you have? What are their ages?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
19~ Who/when was your first “heartbreak”?
Escort/Client Job Applicant/Hiring Manager
70~ Would/do you have/like anal sex?
11~ Have you ever been caught by your parents or children or others while having sex?
15~ Have you ever been “in love”? Who? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
4- For a pet, Cat, dog or other?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
2- What’s your favorite color? Do you a least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
71~ Would you give your partner a hand or foot job? Would you receive one?
26~ What side of the bed do you sleep on?
12- What’s your favorite food? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
If you win, what will you make them do?
Doctor/Nurse Stripper/Client
22~ What is the best pickup line anyone has ever used on you? What was the worst?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What is your favorite toy? Ever wanted to try a specific toy?
*** What’s Your Favorite…? ***
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
10- What is your favorite family tradition? What’s your least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
34~ Do you like the lights on or off during sex?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
(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…)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Model/Photographer Police/Criminal
52~ Are you willing to make “those types” of bets with your partner?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
What would you say to prove to yourself that it was really you?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
31- If given a chance to be immortal, would you take it? Why?
44~ Care to share something about yourself that no one else knows about you?
Master/Slave Boss/Maid
21~ What was the best date you ever went on? What has been the worst?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How many partners have you had oral sex with? Who? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
39~ What are your love languages?
The Ice Breaker Questions
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
29- How superstitious are you?
7-What do I do in bed that drives you wild? How about, what turns you off?
51~ Are you willing to play adult games with your partner?
Any that are a turn off?
If yes, what?
Repairman/Lonely Wife Virgin/Experienced
You know that I will be 100% truthful, so ask.
21- Do you have any piercings? 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?
21- What's your favorite way to spend a weekend or time off?
3- What Superhero or Superpower would you want to be/have?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What is your favorite position? Why?
That one or two things that made you go hmmmm, OMG or wow!
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What do you dislike about me? I asked you to be 100% honest.
3- What’s your favorite smell? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
Nothing too Serious
How many times do you think you have “made love”?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
10~ How many dates are necessary before you to have sex with someone?
Would /have you ever given your partner a lap dance and Striptease?
Family Relation Age Play
Would you allow me to clean every part of your body with my soapy hands and fingers?
*** Questions About Me ***
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?
Would you ever want to be woken up with oral and/or intercourse?
33- Beach or Mountains? Or is there another place to like better?
23- What is your dream job? What was it as a child?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
1- What was your first impression of me? Has it changed?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
27- What was/ is nickname? Does it have a meaning behind it?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
30~ What's something unexpected that turns you on?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
If NO, would you ever have one? Would it be with 2 men or 2 women?
How about if they talk dirty and/or call you names?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Over time has your thoughts on sex changed?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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…
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
10- List 5 of your top pet peeves.
42~ What’s your biggest regret in life?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
How old are you? Male or Female?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
11- How about if they like a certain sports team? 12-How about drinking too much?
Does the thought excite you? Care to share?
Any that are a turn off?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
I would allow you to do it… What would you do to me?
Prisoner/Prison Guard Landlord/Tenant
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
1~ How old were you when you had your first kiss? Who? Care to Share?
Do you like the “69” position? Do you prefer to be on top or bottom?
51~ What tends to bring a smile to your face?
53~ How much can you tell me about the one thing you are most passionate about?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
45~ How do you feel about me blindfolding you? How about blindfolding me?
12- What is the weirdest thing you've ever eaten?
82~ Do you have any fantasies involving Role-Playing?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
*** Deal Breaker Questions ***
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Would you do it again, and would you rather 2 females or 2 males?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
18- How often do you drink alcohol? What is your favorite drink?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
48~ Do you have any siblings? Are you close to your family?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
15- What's your favorite saying? What word or phrase is your least favorite?
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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
29~ What are some things that turn you off? What is your biggest turn off?
7- What if a person smells a certain way? 8- How about smoking?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
If YES, was it with 2 men or 2 women? Did you enjoy it?
47~ What would be your dream job and why?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Do you watch it? What is your favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
32- What's your greatest talent? Can I see it right now?
67~ Do you like it when your partner moans and/or is vocal during sex?
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…
8- What are your thoughts on politics?
34- Ever been to a concert? What was your favorite? Who would you like to see?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?