What is the most interesting question you can ask to get to know someone?
10.06.2025 06:28
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
89~ Do you like taking showers together?
How does an experienced gay/bi guy handle a bi-courius guy on his first time?
82~ Do you have any fantasies involving Role-Playing?
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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
13- How about having a certain hair cut/style?
If NO, would you ever have one? Would it be with 2 men or 2 women?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Would you ever want to be woken up with oral and/or intercourse?
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?
If YES, was it with 2 men or 2 women? Did you enjoy it?
What are the defining characteristics of woke liberals and conservatives in the United States?
Nurse/Patient Celebrity/Fan
33- If you could visit any time period, when would you pick? Please explain why?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
UPDATE: Additional measles exposure locations in Marquette, Delta counties - Upper Michigan's Source
12- What’s your favorite food? What’s your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
13- What’s your favorite drink? What’s your least favorite?
Utah woman loses 100 pounds in one year: Here's how - KSL News
Nothing too Serious
34~ Do you like the lights on or off during sex?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Royals Promote Jac Caglianone - MLB Trade Rumors
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)
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
14- What is an embarrassing moment in your life? How about your most embarrassing?
80~ Share your top three fantasies/desires. (Be detailed) 😊
47~ What would be your dream job and why?
9- If you could have three wishes, what would they be? Why?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
32- What's your greatest talent? Can I see it right now?
Why You Should Stop Texting On Your iPhone Or Android Phone - Forbes
9- What’s your favorite season and why? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
49~ How many times have you been married? Why did they end?
Young researcher’s ALS attack plan is now a no-go - Harvard Gazette
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Part toy, part fashion, the arrival of the viral Labubu was a long time in the making - AP News
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
How well do you know me? And some of your thoughts about me
53~ How much can you tell me about the one thing you are most passionate about?
Get this wrong and this could mean the end… :-) some funny, some not…
11- What's your favorite restaurant? What’s your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Do you like it when they show and tell you what they want?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Would you mind if your partner watched it? How about together vs alone?
36- Do you play video games? What is your favorite? Do you a least favorite?
Doctor/Nurse Stripper/Client
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,
1- What was your first impression of me? Has it changed?
22- Do you have any birth marks? How about scars? Care to share how you got them?
29~ What are some things that turn you off? What is your biggest turn off?
4- For a pet, Cat, dog or other?
42~ What’s your biggest regret in life?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
*** What’s Your Favorite…? ***
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…
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
31- If given a chance to be immortal, would you take it? Why?
If you win, what will you make them do?
17- What’s your favorite holiday? What’s your least favorite?
What have you learned about yourself that you did not before this?
1- What’s your favorite animal? Do you a least favorite?
Do you think this brought you closer together?
If yes, what?
11- List at least 5 things on your bucket list. Have you done any of them already?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
3- Should Pluto still be considered a planet? 4- How about smoking?
If you say it, I will stop, and we can talk about it when you are ready.
What is your favorite position? Why?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
19- What’s your favorite fairytale? What’s your least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Any that are a turn off?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
What was the longest? What was the shortest?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
48~ Have you ever paid or been paid for sex?
*** Questions About Me ***
19~ Who/when was your first “heartbreak”?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Would you allow me to clean every part of your body with my soapy hands and fingers?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Would you read them together?
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?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
28- What are some things that people do that irritate you?
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…
What do you dislike about me? I asked you to be 100% honest.
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What have you learned about me that was new and/or surprising?
83~ How do you feel about Porn?
76~ Have you had a threesome? Care to Share?
* Give a rating for each one (0-100)
*** Questions about Relationships/Past ***
52~ What are your hobbies?
*** Random Questions ***
Over time has your thoughts on sex changed?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
36~ What is your favorite time of day to have sex/make love?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
3- What’s your favorite smell? Do you a least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
11- How about if they like a certain sports team? 12-How about drinking too much?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
I would allow you to do it… What would you do to me?
15- What bad habit do you wish you could quit? Do you have any addictions?
8- What are your thoughts on politics?
7- What if a person smells a certain way? 8- How about smoking?
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?
27- What was/ is nickname? Does it have a meaning behind it?
18- How often do you drink alcohol? What is your favorite drink?
40~ What’s the weirdest place you’ve ever had sex?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Would /have you ever given your partner a lap dance and Striptease?
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?
5~ When you first started having sex, was it what you thought it would be?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Repairman/Lonely Wife Virgin/Experienced
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
11~ Have you ever been caught by your parents or children or others while having sex?
What would you say to prove to yourself that it was really you?
*** Deal Breaker Questions ***
20- What’s your favorite candy? What’s your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
50~ How many children do you have? What are their ages?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
7- What are your thoughts on religion? Is there an afterlife?
23- What is your dream job? What was it as a child?
30~ What's something unexpected that turns you on?
29- How superstitious are you?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Any that are a turn off?
Family Relation Age Play
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
92~ Everyone needs a “safe” word. What is yours?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
Escort/Client Job Applicant/Hiring Manager
51~ What tends to bring a smile to your face?
That one or two things that made you go hmmmm, OMG or wow!
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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?
Master/Slave Boss/Maid
33- Beach or Mountains? Or is there another place to like better?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
10~ How many dates are necessary before you to have sex with someone?
21- What's your favorite way to spend a weekend or time off?
51~ Are you willing to play adult games with your partner?
10- List 5 of your top pet peeves.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Does the thought excite you? Care to share?
12- What is the weirdest thing you've ever eaten?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
Please share Did you stop?
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?
Do you have a favorite? Is it ok if your partner does?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
37- Do you like your name? If you could change it, what would you change it too?
65~ Describe the best orgasm you’ve ever had? Care to share?
48~ Do you have any siblings? Are you close to your family?
62~ Have you used adult toys?
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
How old are you? Male or Female?
1~ How old were you when you had your first kiss? Who? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
9- Is there something you’ve always wanted to ask me but you’re afraid?
61~ How willing would you be to try new sexual positions?
67~ Do you like it when your partner moans and/or is vocal during sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
81~ Do you have any kinks and/or fetishes?
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?
2- What’s your favorite color? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
What is your favorite toy? Ever wanted to try a specific toy?
14- What's your favorite dessert? Do you a least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Prisoner/Prison Guard Landlord/Tenant
64~ When was your very first orgasm? When was your first from having sex? Care to share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
19- Do/have you smoked? What do you prefer? How often?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
17- Have you ever done drugs? Which ones? How often?
How many partners have you had oral sex with? Who? Care to Share?
The Ice Breaker Questions
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Will you cheat again? How can, you be sure? Define what cheating is to you.
13- What is the craziest/scariest thing you've ever done?
25~ How do you feel about PDA? (Public Display of Affection)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
3- What Superhero or Superpower would you want to be/have?
92~ Have you ever had or have an STD? How many? What was it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
84~ How do you feel about reading/listening to adult stories?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Teacher/Student Stranger/One Night Stand
You know that I will be 100% truthful, so ask.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Model/Photographer Police/Criminal
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
Have you ever? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
How many times do you think you have “made love”?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
28~ What are some things that turn on? What is your biggest turn on?
39~ What are your love languages?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
15~ Have you ever been “in love”? Who? Care to Share?
44~ Care to share something about yourself that no one else knows about you?
9~ How many times over your lifetime do you think you have had sex so far?
26~ What side of the bed do you sleep on?
10- What is your favorite family tradition? What’s your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Do you watch it? What is your favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
78~ Have you ever thought about making out or having sex with someone of the same 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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
(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…)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Can you Deep Throat? Do you like the taste of yourself?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
What is your view on sex? Meaning, When/Where/ How often/
70~ Would/do you have/like anal sex?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
18~ Who/when was your first “crush”?