What is the most interesting question you can ask to get to know someone?
Last Updated: 23.06.2025 06:19
Repairman/Lonely Wife Virgin/Experienced
40~ What’s the weirdest place you’ve ever had sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
The Director Of Final Fantasy Tactics Gets Political - Kotaku
11~ Have you ever been caught by your parents or children or others while having sex?
3- What Superhero or Superpower would you want to be/have?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Trump proclamation seeks to restrict international students from Harvard - The Washington Post
22~ What is the best pickup line anyone has ever used on you? What was the worst?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Neurosteroids identified as potential therapy for treatment-resistant depression - Medical Xpress
How about if they talk dirty and/or call you names?
Have you ever? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
Person With Deadly Virus Visited Popular Hudson Valley Restaurant - Hudson Valley Post
7- What if a person smells a certain way? 8- How about smoking?
11- How about if they like a certain sports team? 12-How about drinking too much?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
9- If you could have three wishes, what would they be? Why?
34- Ever been to a concert? What was your favorite? Who would you like to see?
What would you say to prove to yourself that it was really you?
Samsung Galaxy S26 Ultra to continue trend of disappointing batteries - PhoneArena
33- If you could visit any time period, when would you pick? Please explain why?
38~ Share your most embarrassing sexual memory?
71~ Would you give your partner a hand or foot job? Would you receive one?
Forget Florida — these two unexpected states are the new retirement hot spots - Yahoo Finance
89~ Do you like taking showers together?
How many partners have you had oral sex with? Who? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Prelim Results | UFC Fight Night: Blanchfield vs Barber - UFC.com
2- What’s your favorite color? Do you a least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
13~ Is there a difference between, making love, having sex, and fucking?
Jack Betts, ‘Spider-Man’ Actor and Spaghetti Western Veteran, Dies at 96 - Variety
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…
How many times do you think you have “made love”?
52~ Are you willing to make “those types” of bets with your partner?
Amino Acid Supplements Are Trending For A Reason. Here’s Why Dietitians Are Divided. - AOL.com
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
61~ How willing would you be to try new sexual positions?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
92~ Have you ever had or have an STD? How many? What was it?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Would you allow me to clean every part of your body with my soapy hands and fingers?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
That one or two things that made you go hmmmm, OMG or wow!
10~ How many dates are necessary before you to have sex with someone?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
17- Have you ever done drugs? Which ones? How often?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
21- What's your favorite way to spend a weekend or time off?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What is your favorite toy? Ever wanted to try a specific toy?
5~ When you first started having sex, was it what you thought it would be?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
23- What is your dream job? What was it as a child?
29- How superstitious are you?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
I would allow you to do it… What would you do to me?
What have you learned about yourself that you did not before this?
Over time has your thoughts on sex changed?
If NO, would you ever have one? Would it be with 2 men or 2 women?
What do you dislike about me? I asked you to be 100% honest.
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
8- What's your favorite flavor of ice cream? Do you a least favorite?
30~ What's something unexpected that turns you on?
*** Questions about Relationships/Past ***
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
8- What are your thoughts on politics?
Do you like it when they show and tell you what they want?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
12- What’s your favorite food? What’s your least favorite?
51~ Are you willing to play adult games with your partner?
22- Do you have any birth marks? How about scars? Care to share how you got them?
28~ What are some things that turn on? What is your biggest turn on?
If you say it, I will stop, and we can talk about it when you are ready.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
18~ Who/when was your first “crush”?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
29~ What are some things that turn you off? What is your biggest turn off?
25~ How do you feel about PDA? (Public Display of Affection)
10- What is your favorite family tradition? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
26~ What side of the bed do you sleep on?
Please share Did you stop?
21~ What was the best date you ever went on? What has been the worst?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
20- What’s your favorite candy? What’s your least favorite?
Prisoner/Prison Guard Landlord/Tenant
What’s the longest time you gone without having sex, after, having it? How much time between the others?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
17- What’s your favorite holiday? What’s your least favorite?
How well do you know me? And some of your thoughts about me
52~ What are your hobbies?
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?
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)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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…
19~ Who/when was your first “heartbreak”?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Teacher/Student Stranger/One Night Stand
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
(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…)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
83~ How do you feel about Porn?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
67~ Do you like it when your partner moans and/or is vocal during sex?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Would you mind if your partner watched it? How about together vs alone?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
82~ Do you have any fantasies involving Role-Playing?
13- How about having a certain hair cut/style?
76~ Have you had a threesome? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
*** Random Questions ***
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What is your view on sex? Meaning, When/Where/ How often/
13- What’s your favorite drink? What’s your least favorite?
What have you learned about me that was new and/or surprising?
33- Beach or Mountains? Or is there another place to like better?
48~ Do you have any siblings? Are you close to your family?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
65~ Describe the best orgasm you’ve ever had? Care to share?
15- What's your favorite saying? What word or phrase is your least favorite?
19- Do/have you smoked? What do you prefer? How often?
11- List at least 5 things on your bucket list. Have you done any of them already?
If you win, what will you make them do?
44~ Care to share something about yourself that no one else knows about you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Nurse/Patient Celebrity/Fan
Master/Slave Boss/Maid
39~ What are your love languages?
Would /have you ever given your partner a lap dance and Striptease?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
80~ Share your top three fantasies/desires. (Be detailed) 😊
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
4- For a pet, Cat, dog or other?
Would you do it again, and would you rather 2 females or 2 males?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
15- What bad habit do you wish you could quit? Do you have any addictions?
What is your favorite position? Why?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
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- Do you like your name? If you could change it, what would you change it too?
Any that are a turn off?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
15~ Have you ever been “in love”? Who? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
32- What's your greatest talent? Can I see it right now?
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
22- What is your favorite childhood memory? What is your least favorite?
Model/Photographer Police/Criminal
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
50~ How many children do you have? What are their ages?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
10- List 5 of your top pet peeves.
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
9~ How many times over your lifetime do you think you have had sex so far?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
31- If given a chance to be immortal, would you take it? Why?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Any that are a turn off?
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 have a favorite? Is it ok if your partner does?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Will you cheat again? How can, you be sure? Define what cheating is to you.
7-What do I do in bed that drives you wild? How about, what turns you off?
13- What is the craziest/scariest thing you've ever done?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
36~ What is your favorite time of day to have sex/make love?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Would you read them together?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
7- What are your thoughts on religion? Is there an afterlife?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
9- What’s your favorite season and why? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
You know that I will be 100% truthful, so ask.
Would you ever want to be woken up with oral and/or intercourse?
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,
Nothing too Serious
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
70~ Would/do you have/like anal sex?
48~ Have you ever paid or been paid for sex?
* Give a rating for each one (0-100)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
36- Do you play video games? What is your favorite? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
Family Relation Age Play
1- What’s your favorite animal? Do you a least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
28- What are some things that people do that irritate you?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
42~ What’s your biggest regret in life?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What was the longest? What was the shortest?
Get this wrong and this could mean the end… :-) some funny, some not…
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you think this brought you closer together?
49~ How many times have you been married? Why did they end?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Can you Deep Throat? Do you like the taste of yourself?
34~ Do you like the lights on or off during sex?
Do you watch it? What is your favorite?
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?
92~ Everyone needs a “safe” word. What is yours?
1- What was your first impression of me? Has it changed?
Does the thought excite you? Care to share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Doctor/Nurse Stripper/Client
84~ How do you feel about reading/listening to adult stories?
19- What’s your favorite fairytale? What’s your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
*** Deal Breaker Questions ***
12- What is the weirdest thing you've ever eaten?
14- What is an embarrassing moment in your life? How about your most embarrassing?
The Ice Breaker Questions
Escort/Client Job Applicant/Hiring Manager
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
47~ What would be your dream job and why?
If yes, what?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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?
62~ Have you used adult toys?
51~ What tends to bring a smile to your face?
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?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
81~ Do you have any kinks and/or fetishes?
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
*** What’s Your Favorite…? ***
How old are you? Male or Female?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
*** Questions About Me ***