What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 03:11
Would you mind if your partner watched it? How about together vs alone?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Have you ever? Care to Share?
Your Apple CarPlay is getting a big update: 3 useful features coming with iOS 26 - ZDNet
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Please share Did you stop?
Do you agree with Michael Moore that Donald Trump is "toast" in a political comeback?
20- What’s your favorite candy? What’s your least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Why do some people believe that Homelander would be no match for Superman or Thor?
Over time has your thoughts on sex changed?
52~ Are you willing to make “those types” of bets with your partner?
71~ Would you give your partner a hand or foot job? Would you receive one?
Can relationship issues cause depression?
How old are you? Male or Female?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
If Trump were to lose in 2024, would that be the end of his grip on the Republican Party?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
81~ Do you have any kinks and/or fetishes?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
22- What is your favorite childhood memory? What is your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Have husbands and wives ever had a threesome with someone in real life? How did it happen?
28~ What are some things that turn on? What is your biggest turn on?
*** Deal Breaker Questions ***
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
If yes, what?
What do you dislike about me? I asked you to be 100% honest.
1~ How old were you when you had your first kiss? Who? Care to Share?
Your daily horoscope: June 17, 2025 - The Globe and Mail
12- What’s your favorite food? What’s your least favorite?
14- What's your favorite dessert? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Did you become a cuckold for your wife?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Do you watch it? What is your favorite?
Are judges being lenient on hard criminals?
48~ Have you ever paid or been paid for sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Would you ever want to be woken up with oral and/or intercourse?
4- For a pet, Cat, dog or other?
Teacher/Student Stranger/One Night Stand
Will you kiss after your partner has gone down on you? Swallow or spit semen?
33- If you could visit any time period, when would you pick? Please explain why?
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?
13- What is the craziest/scariest thing you've ever done?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What have you learned about yourself that you did not before this?
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?
61~ How willing would you be to try new sexual positions?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
2- What’s your favorite color? Do you a least favorite?
19~ Who/when was your first “heartbreak”?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Nothing too Serious
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
5~ When you first started having sex, was it what you thought it would be?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
*** What’s Your Favorite…? ***
50~ How many children do you have? What are their ages?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
42~ What’s your biggest regret in life?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What is your view on sex? Meaning, When/Where/ How often/
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Doctor/Nurse Stripper/Client
Do you think this brought you closer together?
8- What's your favorite flavor of ice cream? Do you a least favorite?
82~ Do you have any fantasies involving Role-Playing?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
34~ Do you like the lights on or off during sex?
18~ Who/when was your first “crush”?
How about if they talk dirty and/or call you names?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
9- Is there something you’ve always wanted to ask me but you’re afraid?
19- What’s your favorite fairytale? What’s your least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
What would you say to prove to yourself that it was really you?
21~ What was the best date you ever went on? What has been the worst?
Family Relation Age Play
The Ice Breaker Questions
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
If you say it, I will stop, and we can talk about it when you are ready.
65~ Describe the best orgasm you’ve ever had? Care to share?
What have you learned about me that was new and/or surprising?
49~ How many times have you been married? Why did they end?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Does the thought excite you? Care to share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Would you do it again, and would you rather 2 females or 2 males?
11- List at least 5 things on your bucket list. Have you done any of them already?
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
18- How often do you drink alcohol? What is your favorite drink?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Would you read them together?
10- What is your favorite family tradition? What’s your least favorite?
How many times do you think you have “made love”?
13- What’s your favorite drink? What’s your least favorite?
7- What if a person smells a certain way? 8- How about smoking?
52~ What are your hobbies?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
33- Beach or Mountains? Or is there another place to like better?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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…
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Escort/Client Job Applicant/Hiring Manager
34- Ever been to a concert? What was your favorite? Who would you like to see?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Can you Deep Throat? Do you like the taste of yourself?
89~ Do you like taking showers together?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Would you allow me to clean every part of your body with my soapy hands and fingers?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
*** Questions About Me ***
35- Do you like playing board or cards game? What is your favorite? 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?
What is your favorite toy? Ever wanted to try a specific toy?
11~ Have you ever been caught by your parents or children or others while having sex?
17- What’s your favorite holiday? What’s your least favorite?
29- How superstitious are you?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
44~ Care to share something about yourself that no one else knows about you?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
10~ How many dates are necessary before you to have sex with someone?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
45~ How do you feel about me blindfolding you? How about blindfolding me?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
3- What Superhero or Superpower would you want to be/have?
32- What's your greatest talent? Can I see it right now?
51~ What tends to bring a smile to your face?
Any that are a turn off?
Repairman/Lonely Wife Virgin/Experienced
* Give a rating for each one (0-100)
26~ What side of the bed do you sleep on?
3- What’s your favorite smell? Do you a least favorite?
8- What are your thoughts on politics?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
5- Have you ever been hypnotized? Would you allow yourself to be?
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?
What was the longest? What was the shortest?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
47~ What would be your dream job and why?
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)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
*** Random Questions ***
36- Do you play video games? What is your favorite? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
7- What are your thoughts on religion? Is there an afterlife?
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?
1- What was your first impression of me? Has it changed?
*** Questions about Relationships/Past ***
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
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?
13- How about having a certain hair cut/style?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
31- If given a chance to be immortal, would you take it? Why?
92~ Everyone needs a “safe” word. What is yours?
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 is your favorite position? Why?
Prisoner/Prison Guard Landlord/Tenant
If you win, what will you make them do?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
92~ Have you ever had or have an STD? How many? What was it?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
13~ Is there a difference between, making love, having sex, and fucking?
1- What’s your favorite animal? Do you a least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
22- Do you have any birth marks? How about scars? Care to share how you got them?
36~ What is your favorite time of day to have sex/make love?
Do you have a favorite? Is it ok if your partner does?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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,
76~ Have you had a threesome? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
37- Do you like your name? If you could change it, what would you change it too?
21- What's your favorite way to spend a weekend or time off?
29~ What are some things that turn you off? What is your biggest turn off?
30~ What's something unexpected that turns you on?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
14- What is an embarrassing moment in your life? How about your most embarrassing?
51~ Are you willing to play adult games with your partner?
67~ Do you like it when your partner moans and/or is vocal during sex?
3- Should Pluto still be considered a planet? 4- How about smoking?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
How many partners have you had oral sex with? Who? Care to Share?
28- What are some things that people do that irritate you?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
You know that I will be 100% truthful, so ask.
Do you like it when they show and tell you what they want?
84~ How do you feel about reading/listening to adult stories?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
64~ When was your very first orgasm? When was your first from having sex? 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…)
12- What is the weirdest thing you've ever eaten?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
38~ Share your most embarrassing sexual memory?
9- If you could have three wishes, what would they be? Why?
83~ How do you feel about Porn?
If YES, was it with 2 men or 2 women? Did you enjoy it?
48~ Do you have any siblings? Are you close to your family?
62~ Have you used adult toys?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
10- List 5 of your top pet peeves.
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?
27- What was/ is nickname? Does it have a meaning behind it?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
25~ How do you feel about PDA? (Public Display of Affection)
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
I would allow you to do it… What would you do to me?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
39~ What are your love languages?
7-What do I do in bed that drives you wild? How about, what turns you off?
Model/Photographer Police/Criminal
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Master/Slave Boss/Maid
That one or two things that made you go hmmmm, OMG or wow!
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?
23- What is your dream job? What was it as a child?
17- Have you ever done drugs? Which ones? How often?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Do you like the “69” position? Do you prefer to be on top or bottom?
How well do you know me? And some of your thoughts about me
9~ How many times over your lifetime do you think you have had sex so far?
Any that are a turn off?
53~ How much can you tell me about the one thing you are most passionate about?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Nurse/Patient Celebrity/Fan
11- What's your favorite restaurant? What’s your least favorite?