What is the most interesting question you can ask to get to know someone?
09.06.2025 01:14
9- Is there something you’ve always wanted to ask me but you’re afraid?
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?
22- What is your favorite childhood memory? What is your least favorite?
What have you learned about yourself that you did not before this?
3- Should Pluto still be considered a planet? 4- How about smoking?
NASA’s Webb Rounds Out Picture of Sombrero Galaxy’s Disk - NASA Science (.gov)
Prisoner/Prison Guard Landlord/Tenant
19- What’s your favorite fairytale? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
Why are women attracted to ugly guys?
28- What are some things that people do that irritate you?
Model/Photographer Police/Criminal
Can you Deep Throat? Do you like the taste of yourself?
How many partners have you had oral sex with? Who? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What Makes the Florida Panthers Special? Gaudreau Tribute a Fine Example - Florida Hockey Now
27- What was/ is nickname? Does it have a meaning behind it?
37- Do you like your name? If you could change it, what would you change it too?
10- List 5 of your top pet peeves.
Why do our deceased do not protect us from other bad spirits?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Why are leftist movements so popular among young people?
19- Do/have you smoked? What do you prefer? How often?
13- How about having a certain hair cut/style?
81~ Do you have any kinks and/or fetishes?
Your TRICARE Checklist for Moving - TRICARE Newsroom (.mil)
*** Deal Breaker Questions ***
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Over time has your thoughts on sex changed?
49~ How many times have you been married? Why did they end?
7- What are your thoughts on religion? Is there an afterlife?
34- Ever been to a concert? What was your favorite? Who would you like to see?
What is your review of X-Men '97 season 1?
Do you think this brought you closer together?
34~ Do you like the lights on or off during sex?
11- How about if they like a certain sports team? 12-How about drinking too much?
Are there any penalties for bestiality in the USA and laws prohibiting it?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Nurse/Patient Celebrity/Fan
What do you dislike about me? I asked you to be 100% honest.
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
* Give a rating for each one (0-100)
18- How often do you drink alcohol? What is your favorite drink?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
15- What's your favorite saying? What word or phrase is your least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
52~ What are your hobbies?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
If you win, what will you make them do?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
That one or two things that made you go hmmmm, OMG or wow!
17- What’s your favorite holiday? What’s 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?
Would you read them together?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Would you do it again, and would you rather 2 females or 2 males?
Escort/Client Job Applicant/Hiring Manager
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
12- What’s your favorite food? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Master/Slave Boss/Maid
39~ What are your love languages?
1~ How old were you when you had your first kiss? Who? Care to Share?
5- Have you ever been hypnotized? Would you allow yourself to be?
76~ Have you had a threesome? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
21~ What was the best date you ever went on? What has been the worst?
40~ What’s the weirdest place you’ve ever had sex?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
I would allow you to do it… What would you do to me?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
18~ Who/when was your first “crush”?
8- What's your favorite flavor of ice cream? Do you a least favorite?
19~ Who/when was your first “heartbreak”?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
*** Questions about Relationships/Past ***
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How many times do you think you have “made love”?
*** Random Questions ***
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
45~ How do you feel about me blindfolding you? How about blindfolding me?
36~ What is your favorite time of day to have sex/make love?
38~ Share your most embarrassing sexual memory?
21- What's your favorite way to spend a weekend or time off?
1- What was your first impression of me? Has it changed?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
3- What’s your favorite smell? Do you a least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Family Relation Age Play
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
42~ What’s your biggest regret in life?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Have you ever? Care to Share?
What is your favorite position? Why?
89~ Do you like taking showers together?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Would you mind if your partner watched it? How about together vs alone?
3- What Superhero or Superpower would you want to be/have?
25~ How do you feel about PDA? (Public Display of Affection)
The Ice Breaker Questions
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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…
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
83~ How do you feel about Porn?
2- What’s your favorite color? Do you a least favorite?
10- What is your favorite family tradition? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
33- Beach or Mountains? Or is there another place to like better?
9~ How many times over your lifetime do you think you have had sex so far?
Do you have a favorite? Is it ok if your partner does?
51~ Are you willing to play adult games with your partner?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
Do you like the “69” position? Do you prefer to be on top or bottom?
Any that are a turn off?
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…
82~ Do you have any fantasies involving Role-Playing?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
How old are you? Male or Female?
11- What's your favorite restaurant? What’s your 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…)
*** Questions About Me ***
If NO, would you ever have one? Would it be with 2 men or 2 women?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
*** What’s Your Favorite…? ***
Would you allow me to clean every part of your body with my soapy hands and fingers?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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)
61~ How willing would you be to try new sexual positions?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
62~ Have you used adult toys?
7- What if a person smells a certain way? 8- How about smoking?
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?
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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
How about if they talk dirty and/or call you names?
4- For a pet, Cat, dog or other?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
23- What is your dream job? What was it as a child?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
26~ What side of the bed do you sleep on?
28~ What are some things that turn on? What is your biggest turn on?
15- What bad habit do you wish you could quit? Do you have any addictions?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If yes, what?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
70~ Would/do you have/like anal sex?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Repairman/Lonely Wife Virgin/Experienced
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Does the thought excite you? Care to share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
65~ Describe the best orgasm you’ve ever had? Care to share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Get this wrong and this could mean the end… :-) some funny, some not…
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,
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
You know that I will be 100% truthful, so ask.
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
50~ How many children do you have? What are their ages?
33- If you could visit any time period, when would you pick? Please explain why?
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?
29- How superstitious are you?
10~ How many dates are necessary before you to have sex with someone?
9- If you could have three wishes, what would they be? Why?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Do you like it when they show and tell you what they want?
Nothing too Serious
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
92~ Everyone needs a “safe” word. What is yours?
17- Have you ever done drugs? Which ones? How often?
14- What's your favorite dessert? Do you a least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
11- List at least 5 things on your bucket list. Have you done any of them already?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
71~ Would you give your partner a hand or foot job? Would you receive one?
11~ Have you ever been caught by your parents or children or others while having sex?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Teacher/Student Stranger/One Night Stand
If you say it, I will stop, and we can talk about it when you are ready.
Do you watch it? What is your favorite?
9- What’s your favorite season and why? What’s your least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What is your favorite toy? Ever wanted to try a specific toy?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Would you ever want to be woken up with oral and/or intercourse?
12- What is the weirdest thing you've ever eaten?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
20- What’s your favorite candy? What’s your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
48~ Have you ever paid or been paid for sex?
13~ Is there a difference between, making love, having sex, and fucking?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
1- What’s your favorite animal? Do you a least favorite?
Any that are a turn off?
32- What's your greatest talent? Can I see it right now?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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?
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?
47~ What would be your dream job and why?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
30~ What's something unexpected that turns you on?
7-What do I do in bed that drives you wild? How about, what turns you off?
29~ What are some things that turn you off? What is your biggest turn off?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
5~ When you first started having sex, was it what you thought it would be?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What have you learned about me that was new and/or surprising?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
31- If given a chance to be immortal, would you take it? Why?
Please share Did you stop?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Would /have you ever given your partner a lap dance and Striptease?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
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?
48~ Do you have any siblings? Are you close to your family?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Doctor/Nurse Stripper/Client
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What is your view on sex? Meaning, When/Where/ How often/
92~ Have you ever had or have an STD? How many? What was it?
13- What is the craziest/scariest thing you've ever done?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
How well do you know me? And some of your thoughts about me
36- Do you play video games? What is your favorite? Do you a least favorite?
44~ Care to share something about yourself that no one else knows about you?
8- What are your thoughts on politics?
51~ What tends to bring a smile to your face?
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
14- What is an embarrassing moment in your life? How about your most embarrassing?
84~ How do you feel about reading/listening to adult stories?
53~ How much can you tell me about the one thing you are most passionate about?
52~ Are you willing to make “those types” of bets with your partner?
Will you cheat again? How can, you be sure? Define what cheating is to you.