What is the most interesting question you can ask to get to know someone?
08.06.2025 04:08
27- What was/ is nickname? Does it have a meaning behind it?
Escort/Client Job Applicant/Hiring Manager
Do you shave/trim your pubic hair? For you guys do you shave your balls?
How Cocaine Hijacks the Brain - Neuroscience News
2- What’s your favorite color? Do you a least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Do narcissists love their children?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
52~ Are you willing to make “those types” of bets with your partner?
Yuen: When cancer struck a second time, she found ‘euphoria’ - Star Tribune
26~ What side of the bed do you sleep on?
3- Should Pluto still be considered a planet? 4- How about smoking?
Would you allow me to clean every part of your body with my soapy hands and fingers?
What are some common lies that addicts may tell themselves?
89~ Do you like taking showers together?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Get this wrong and this could mean the end… :-) some funny, some not…
Elden Ring Nightreign devs confirm they’re working on a duos mode - Polygon
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
14- What is an embarrassing moment in your life? How about your most embarrassing?
Please share Did you stop?
33- Beach or Mountains? Or is there another place to like better?
13~ Is there a difference between, making love, having sex, and fucking?
Do you think this brought you closer together?
What is the best sex you have ever had (in detail)?
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?
42~ What’s your biggest regret in life?
39~ What are your love languages?
12- What’s your favorite food? What’s your least favorite?
1- What’s your favorite animal? Do you a least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What were some of the unforgettable incidents from your school life?
*** Deal Breaker Questions ***
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Is the Las Vegas Grand Prix considered one of the "premier events on the Formula 1 calendar?"
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Any that are a turn off?
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?
What would you say to prove to yourself that it was really you?
Nothing too Serious
70~ Would/do you have/like anal sex?
What the ‘Revenge Tax’ Is in the Tax Bill—and How It Could Pummel the Dollar - Barron's
*** What’s Your Favorite…? ***
76~ Have you had a threesome? Care to Share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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,
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
That one or two things that made you go hmmmm, OMG or wow!
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
92~ Have you ever had or have an STD? How many? What was it?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
19- Do/have you smoked? What do you prefer? How often?
11~ Have you ever been caught by your parents or children or others while having sex?
10~ How many dates are necessary before you to have sex with someone?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
10- What is your favorite family tradition? What’s your least favorite?
52~ What are your hobbies?
12- What is the weirdest thing you've ever eaten?
61~ How willing would you be to try new sexual positions?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Does the thought excite you? Care to share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
15- What bad habit do you wish you could quit? Do you have any addictions?
*** Questions about Relationships/Past ***
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Would you ever want to be woken up with oral and/or intercourse?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
18~ Who/when was your first “crush”?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
36~ What is your favorite time of day to have sex/make love?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
80~ Share your top three fantasies/desires. (Be detailed) 😊
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
34~ Do you like the lights on or off during sex?
13- How about having a certain hair cut/style?
31- If given a chance to be immortal, would you take it? Why?
Would you read them together?
23- What is your dream job? What was it as a child?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
47~ What would be your dream job and why?
84~ How do you feel about reading/listening to adult stories?
38~ Share your most embarrassing sexual memory?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would /have you ever given your partner a lap dance and Striptease?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
10- List 5 of your top pet peeves.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
11- List at least 5 things on your bucket list. Have you done any of them already?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What was the longest? What was the shortest?
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…
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
3- What Superhero or Superpower would you want to be/have?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
If yes, what?
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?
What do you dislike about me? I asked you to be 100% honest.
49~ How many times have you been married? Why did they end?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
9- If you could have three wishes, what would they be? Why?
50~ How many children do you have? What are their ages?
7-What do I do in bed that drives you wild? How about, what turns you off?
83~ How do you feel about Porn?
Any that are a turn off?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Doctor/Nurse Stripper/Client
45~ How do you feel about me blindfolding you? How about blindfolding me?
8- What are your thoughts on politics?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
If you say it, I will stop, and we can talk about it when you are ready.
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
19~ Who/when was your first “heartbreak”?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
5- Have you ever been hypnotized? Would you allow yourself to be?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Teacher/Student Stranger/One Night Stand
Can you Deep Throat? Do you like the taste of yourself?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
22- What is your favorite childhood memory? What is your least favorite?
Do you have a favorite? Is it ok if your partner does?
21- What's your favorite way to spend a weekend or time off?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
48~ Have you ever paid or been paid for sex?
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?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
30~ What's something unexpected that turns you on?
19- What’s your favorite fairytale? What’s your least favorite?
36- Do you play video games? What is your favorite? Do you a 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?
Model/Photographer Police/Criminal
21~ What was the best date you ever went on? What has been the worst?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
9- What’s your favorite season and why? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
32- What's your greatest talent? Can I see it right now?
13- What is the craziest/scariest thing you've ever done?
7- What if a person smells a certain way? 8- How about smoking?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Prisoner/Prison Guard Landlord/Tenant
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How many times do you think you have “made love”?
Repairman/Lonely Wife Virgin/Experienced
How many partners have you had oral sex with? Who? Care to Share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
7- What’s your favorite book? Do you have a favorite genre? 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?
If you win, what will you make them do?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
81~ Do you have any kinks and/or fetishes?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Master/Slave Boss/Maid
The Ice Breaker Questions
1~ How old were you when you had your first kiss? Who? Care to Share?
*** Questions About Me ***
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
17- Have you ever done drugs? Which ones? How often?
53~ How much can you tell me about the one thing you are most passionate about?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
28~ What are some things that turn on? What is your biggest turn on?
51~ Are you willing to play adult games with your partner?
3- What’s your favorite smell? Do you a least favorite?
28- What are some things that people do that irritate you?
Family Relation Age Play
13- What’s your favorite drink? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
I would allow you to do it… What would you do to me?
62~ Have you used adult toys?
29- How superstitious are you?
51~ What tends to bring a smile to your face?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
4- For a pet, Cat, dog or other?
What is your view on sex? Meaning, When/Where/ How often/
How about if they talk dirty and/or call you names?
How old are you? Male or Female?
9~ How many times over your lifetime do you think you have had sex so far?
20- What’s your favorite candy? What’s your least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
37- Do you like your name? If you could change it, what would you change it too?
40~ What’s the weirdest place you’ve ever had sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Would you mind if your partner watched it? How about together vs alone?
17- What’s your favorite holiday? What’s your least favorite?
11- What's your favorite restaurant? What’s your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Have you ever? Care to Share?
* Give a rating for each one (0-100)
You know that I will be 100% truthful, so ask.
What have you learned about yourself that you did not before this?
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
7- What are your thoughts on religion? Is there an afterlife?
22- Do you have any birth marks? How about scars? Care to share how you got them?
How well do you know me? And some of your thoughts about me
48~ Do you have any siblings? Are you close to your family?
(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…)
1- What was your first impression of me? Has it changed?
Would you do it again, and would you rather 2 females or 2 males?
What is your favorite toy? Ever wanted to try a specific toy?
44~ Care to share something about yourself that no one else knows about you?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
*** Random Questions ***
65~ Describe the best orgasm you’ve ever had? Care to share?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
15- What's your favorite saying? What word or phrase is your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
18- How often do you drink alcohol? What is your favorite drink?
Nurse/Patient Celebrity/Fan
5~ When you first started having sex, was it what you thought it would be?
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?
Do you watch it? What is your favorite?
Do you like it when they show and tell you what they want?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
29~ What are some things that turn you off? What is your biggest turn off?
14- What's your favorite dessert? Do you a least 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…
92~ Everyone needs a “safe” word. What is yours?
25~ How do you feel about PDA? (Public Display of Affection)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
What is your favorite position? Why?
33- If you could visit any time period, when would you pick? Please explain why?
What have you learned about me that was new and/or surprising?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Over time has your thoughts on sex changed?