What is the most interesting question you can ask to get to know someone?
15.06.2025 08:16

38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
71~ Would you give your partner a hand or foot job? Would you receive one?
4- For a pet, Cat, dog or other?
23- What is your dream job? What was it as a child?
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?
Why do so many 18 to 29-year-old men struggle in dating?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
7- What are your thoughts on religion? Is there an afterlife?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What are the pros and cons of a prospective bride/groom not having any siblings?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
6- Do you have dreams? Can you remember them? What do you usually dream about?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
38~ Share your most embarrassing sexual memory?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you read them together?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
39~ What are your love languages?
17- Have you ever done drugs? Which ones? How often?
34~ Do you like the lights on or off during sex?
42~ Whatâs your biggest regret in life?
8- What's your favorite flavor of ice cream? Do you a least favorite?
NBA Trade Rumors Roundup: Kevin Durant trade could happen soon, Clippers in the mix - NBC Sports
21~ What was the best date you ever went on? What has been the worst?
Nothing too Serious
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
How is sex with a woman for gay men?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
14- What's your favorite dessert? Do you a least favorite?
Take the short quiz here @ Discover Your Love LanguageÂŽ - The 5 Love LanguagesÂŽ
Can you summarize season 1 of "The Acolyte"?
11~ Have you ever been caught by your parents or children or others while having sex?
Nurse/Patient Celebrity/Fan
What is your view on sex? Meaning, When/Where/ How often/
Do you like the â69â position? Do you prefer to be on top or bottom?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Why do some guys treat girls so badly?
Prisoner/Prison Guard Landlord/Tenant
9- Is there something youâve always wanted to ask me but youâre afraid?
Do you think this brought you closer together?
Atheists who have read the Bible and think that contains immoral things, why do you assume that?
17- Whatâs your favorite holiday? Whatâs your least favorite?
Teacher/Student Stranger/One Night Stand
13- Whatâs your favorite drink? Whatâs your least favorite?
What is your favorite cuckold experience?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If you win, what will you make them do?
92~ Everyone needs a âsafeâ word. What is yours?
Why don't I get sleep at nights?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Does the thought excite you? Care to share?
89~ Do you like taking showers together?
What are the best items to buy from a furniture shop?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
50~ How many children do you have? What are their ages?
Escort/Client Job Applicant/Hiring Manager
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
If you say it, I will stop, and we can talk about it when you are ready.
You know that I will be 100% truthful, so ask.
* Give a rating for each one (0-100)
If NO, would you ever have one? Would it be with 2 men or 2 women?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
What would you say to prove to yourself that it was really you?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
10- What is your favorite family tradition? Whatâs your least favorite?
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?
What is your favorite toy? Ever wanted to try a specific toy?
14- What is an embarrassing moment in your life? How about your most embarrassing?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
81~ Do you have any kinks and/or fetishes?
28~ What are some things that turn on? What is your biggest turn on?
70~ Would/do you have/like anal sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Please share Did you stop?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
84~ How do you feel about reading/listening to adult stories?
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
*** Whatâs Your FavoriteâŚ? ***
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŚ
11- List at least 5 things on your bucket list. Have you done any of them already?
11- What's your favorite restaurant? Whatâs your least favorite?
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?
Would you ever want to be woken up with oral and/or intercourse?
9- Whatâs your favorite season and why? Whatâs your least favorite?
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What was the longest? What was the shortest?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
44~ Care to share something about yourself that no one else knows about you?
What have you learned about me that was new and/or surprising?
Any that are a turn off?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
*** Questions about Relationships/Past ***
12- What is the weirdest thing you've ever eaten?
33- If you could visit any time period, when would you pick? Please explain why?
That one or two things that made you go hmmmm, OMG or wow!
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 togetherâŚ
60~ How important is oral sex? Do you like receiving? Do you like giving?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
3- What was the most surprising thing youâve learned about me throughout our relationship?
7-What do I do in bed that drives you wild? How about, what turns you off?
1- What was your first impression of me? Has it changed?
The Ice Breaker Questions
13- How about having a certain hair cut/style?
Would you do it again, and would you rather 2 females or 2 males?
Do you have a favorite? Is it ok if your partner does?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
1~ How old were you when you had your first kiss? Who? Care to Share?
Model/Photographer Police/Criminal
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
48~ Do you have any siblings? Are you close to your family?
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?
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
37- Do you like your name? If you could change it, what would you change it too?
Family Relation Age Play
How old are you? Male or Female?
Master/Slave Boss/Maid
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
15- What bad habit do you wish you could quit? Do you have any addictions?
76~ Have you had a threesome? Care to Share?
13- What is the craziest/scariest thing you've ever done?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
Repairman/Lonely Wife Virgin/Experienced
Piecing, tattoo, color hair, dress up a certain way, it could be anything⌠Shave meâŚ
51~ Are you willing to play adult games with your partner?
*** Deal Breaker Questions ***
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
10~ How many dates are necessary before you to have sex with someone?
5~ When you first started having sex, was it what you thought it would be?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
27- What was/ is nickname? Does it have a meaning behind it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
85~ If you gave me a âfree Passâ to have me do anything for one hour, what would you want me to do to you?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
34- Ever been to a concert? What was your favorite? Who would you like to see?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŚ
65~ Describe the best orgasm youâve ever had? Care to share?
80~ Share your top three fantasies/desires. (Be detailed) đ
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
18~ Who/when was your first âcrushâ?
19- Whatâs your favorite fairytale? Whatâs your least favorite?
30~ What's something unexpected that turns you on?
83~ How do you feel about Porn?
Over time has your thoughts on sex changed?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
5- Have you ever been hypnotized? Would you allow yourself to be?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
11- How about if they like a certain sports team? 12-How about drinking too much?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
10- List 5 of your top pet peeves.
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
9~ How many times over your lifetime do you think you have had sex so far?
12- Whatâs your favorite food? Whatâs your least favorite?
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?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you watch it? What is your favorite?
36~ What is your favorite time of day to have sex/make love?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
82~ Do you have any fantasies involving Role-Playing?
15~ Have you ever been âin loveâ? Who? Care to Share?
20- Whatâs your favorite candy? Whatâs your least favorite?
49~ How many times have you been married? Why did they end?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
*** Random Questions ***
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 âPASSâ 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 yourselfâŚ
Would /have you ever given your partner a lap dance and Striptease?
51~ What tends to bring a smile to your face?
19- Do/have you smoked? What do you prefer? How often?
What do you dislike about me? I asked you to be 100% honest.
52~ Are you willing to make âthose typesâ of bets with your partner?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
If YES, was it with 2 men or 2 women? Did you enjoy it?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Have you ever? Care to Share?
52~ What are your hobbies?
1- Whatâs your favorite animal? Do you a least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
How many times do you think you have âmade loveâ?
45~ How do you feel about me blindfolding you? How about blindfolding me?
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
3- Should Pluto still be considered a planet? 4- How about smoking?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
If yes, what?
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)
Any that are a turn off?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
28- What are some things that people do that irritate you?
21- What's your favorite way to spend a weekend or time off?
64~ When was your very first orgasm? When was your first from having sex? 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?
7- What if a person smells a certain way? 8- How about smoking?
26~ What side of the bed do you sleep on?
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
2- Whatâs your favorite color? Do you a least favorite?
*** Questions About Me ***
29- How superstitious are you?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Do you like it when they show and tell you what they want?
14 â Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
22- What is your favorite childhood memory? What is your least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
22- Do you have any birth marks? How about scars? Care to share how you got them?
18- How often do you drink alcohol? What is your favorite drink?
9- If you could have three wishes, what would they be? Why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
19~ Who/when was your first âheartbreakâ?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
25~ How do you feel about PDA? (Public Display of Affection)
Would you mind if your partner watched it? How about together vs alone?
31- If given a chance to be immortal, would you take it? Why?
Doctor/Nurse Stripper/Client
62~ Have you used adult toys?
Can you Deep Throat? Do you like the taste of yourself?
Would you allow me to clean every part of your body with my soapy hands and fingers?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What is your favorite position? Why?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
I would allow you to do it⌠What would you do to me?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
85~ If I gave you a âFree Passâ for you to do anything to me for one hour, knowing that no matter what you did,
36- Do you play video games? What is your favorite? Do you a least favorite?
How about if they talk dirty and/or call you names?
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couplesâ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETCâŚ)
3- Whatâs your favorite smell? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
61~ How willing would you be to try new sexual positions?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
67~ Do you like it when your partner moans and/or is vocal during sex?
3- What Superhero or Superpower would you want to be/have?
32- What's your greatest talent? Can I see it right now?
What have you learned about yourself that you did not before this?
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
33- Beach or Mountains? Or is there another place to like better?
40~ Whatâs the weirdest place youâve ever had sex?
Get this wrong and this could mean the end⌠:-) some funny, some notâŚ
14- Do you have a âDeal Breakerâ, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
48~ Have you ever paid or been paid for sex?
How well do you know me? And some of your thoughts about me