What is the most interesting question you can ask to get to know someone?
Last Updated: 03.07.2025 02:52
21~ What was the best date you ever went on? What has been the worst?
Nurse/Patient Celebrity/Fan
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Risk Of Dengue Fever Is Just Another Reason Cruises Suck - Jalopnik
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
1- What was your first impression of me? Has it changed?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
CFPB enforcement lead resigns, slams ‘attack’ on core mission in departure email - CNN
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Model/Photographer Police/Criminal
29~ What are some things that turn you off? What is your biggest turn off?
What does pompano fish taste like?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
If you say it, I will stop, and we can talk about it when you are ready.
5~ When you first started having sex, was it what you thought it would be?
We Asked Dietitians Their Favorite High- Protein Snacks—Here's The Top 9 - health.com
You know that I will be 100% truthful, so ask.
7- What are your thoughts on religion? Is there an afterlife?
Can you Deep Throat? Do you like the taste of yourself?
Rossendale man 'did not know what was wrong until I got NHS text' - BBC
Have you ever? Care to Share?
If yes, what?
61~ How willing would you be to try new sexual positions?
Housing market tide is turning as home prices fall in top cities - Fortune
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
47~ What would be your dream job and why?
20- What’s your favorite candy? What’s your least favorite?
4- For a pet, Cat, dog or other?
Children of slain Minnesota lawmaker Melissa Hortman: 'We are devastated' - ABC News
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
If YES, was it with 2 men or 2 women? Did you enjoy it?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Are there scientific studies that support the detox benefits of an infrared sauna blanket?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Which bands became massively popular for covering songs rather than recording originals?
13- How about having a certain hair cut/style?
*** What’s Your Favorite…? ***
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
5 Things to Know Before the Stock Market Opens - Investopedia
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
How many times do you think you have “made love”?
Shouldn’t there be a short porn platform like TikTok?
38~ Share your most embarrassing sexual memory?
14- What is an embarrassing moment in your life? How about your most embarrassing?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Any that are a turn off?
That one or two things that made you go hmmmm, OMG or wow!
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
* Give a rating for each one (0-100)
5- Have you ever been hypnotized? Would you allow yourself to be?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Doctor/Nurse Stripper/Client
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…
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
If you win, what will you make them do?
12- What’s your favorite food? What’s your least favorite?
Any that are a turn off?
92~ Everyone needs a “safe” word. What is yours?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
83~ How do you feel about Porn?
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 you ever want to be woken up with oral and/or intercourse?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
25~ How do you feel about PDA? (Public Display of Affection)
60~ How important is oral sex? Do you like receiving? Do you like giving?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
7-What do I do in bed that drives you wild? How about, what turns you off?
45~ How do you feel about me blindfolding you? How about blindfolding me?
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 think this brought you closer together?
Do you watch it? What is your favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
28~ What are some things that turn on? What is your biggest turn on?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
26~ What side of the bed do you sleep on?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
How well do you know me? And some of your thoughts about me
What have you learned about me that was new and/or surprising?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
What do you dislike about me? I asked you to be 100% honest.
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Repairman/Lonely Wife Virgin/Experienced
31- If given a chance to be immortal, would you take it? Why?
9- If you could have three wishes, what would they be? Why?
9- Is there something you’ve always wanted to ask me but you’re afraid?
*** Random Questions ***
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
21- What's your favorite way to spend a weekend or time off?
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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
(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…)
Teacher/Student Stranger/One Night Stand
I would allow you to do it… What would you do to me?
How many partners have you had oral sex with? Who? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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,
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
Does the thought excite you? Care to share?
37- Do you like your name? If you could change it, what would you change it too?
19- Do/have you smoked? What do you prefer? How often?
Would you read them together?
Do you have a favorite? Is it ok if your partner does?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What is your view on sex? Meaning, When/Where/ How often/
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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)
7- What if a person smells a certain way? 8- How about smoking?
What have you learned about yourself that you did not before this?
34~ Do you like the lights on or off during sex?
15- What bad habit do you wish you could quit? Do you have any addictions?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
67~ Do you like it when your partner moans and/or is vocal during sex?
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
13~ Is there a difference between, making love, having sex, and fucking?
44~ Care to share something about yourself that no one else knows about you?
Please share Did you stop?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
13- What is the craziest/scariest thing you've ever done?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
2- What’s your favorite color? Do you a least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Master/Slave Boss/Maid
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
51~ Are you willing to play adult games with your partner?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
48~ Do you have any siblings? Are you close to your family?
11- List at least 5 things on your bucket list. Have you done any of them already?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
10- What is your favorite family tradition? What’s your least favorite?
3- What Superhero or Superpower would you want to be/have?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
9- What’s your favorite season and why? What’s your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
12- What is the weirdest thing you've ever eaten?
10~ How many dates are necessary before you to have sex with someone?
What is your favorite toy? Ever wanted to try a specific toy?
42~ What’s your biggest regret in life?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
51~ What tends to bring a smile to your face?
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?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Escort/Client Job Applicant/Hiring Manager
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
92~ Have you ever had or have an STD? How many? What was it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Do you like it when they show and tell you what they want?
33- Beach or Mountains? Or is there another place to like better?
11- What's your favorite restaurant? What’s your least favorite?
49~ How many times have you been married? Why did they end?
28- What are some things that people do that irritate you?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
19~ Who/when was your first “heartbreak”?
29- How superstitious are you?
65~ Describe the best orgasm you’ve ever had? Care to share?
30~ What's something unexpected that turns you on?
52~ What are your hobbies?
40~ What’s the weirdest place you’ve ever had sex?
84~ How do you feel about reading/listening to adult stories?
33- If you could visit any time period, when would you pick? Please explain why?
18~ Who/when was your first “crush”?
62~ Have you used adult toys?
What was the longest? What was the shortest?
Over time has your thoughts on sex changed?
How old are you? Male or Female?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Get this wrong and this could mean the end… :-) some funny, some not…
48~ Have you ever paid or been paid for sex?
*** Questions About Me ***
If NO, would you ever have one? Would it be with 2 men or 2 women?
89~ Do you like taking showers together?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
What is your favorite position? Why?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
9~ How many times over your lifetime do you think you have had sex so far?
32- What's your greatest talent? Can I see it right now?
Family Relation Age Play
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
19- What’s your favorite fairytale? What’s your least favorite?
The Ice Breaker Questions
50~ How many children do you have? What are their ages?
17- What’s your favorite holiday? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
Prisoner/Prison Guard Landlord/Tenant
3- What was the most surprising thing you’ve learned about me throughout our relationship?
13- What’s your favorite drink? 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?
36~ What is your favorite time of day to have sex/make love?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
11~ Have you ever been caught by your parents or children or others while having sex?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
53~ How much can you tell me about the one thing you are most passionate about?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
23- What is your dream job? What was it as a child?
How about if they talk dirty and/or call you names?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
17- Have you ever done drugs? Which ones? How often?
15- What's your favorite saying? What word or phrase is your least favorite?
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
1- What’s your favorite animal? Do you a least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
8- What are your thoughts on politics?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
39~ What are your love languages?
Will you cheat again? How can, you be sure? Define what cheating is to you.
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
10- List 5 of your top pet peeves.
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
15~ Have you ever been “in love”? Who? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
Nothing too Serious
Do you like the “69” position? Do you prefer to be on top or bottom?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
*** Deal Breaker Questions ***
Would /have you ever given your partner a lap dance and Striptease?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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…
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
What would you say to prove to yourself that it was really you?
*** Questions about Relationships/Past ***
Would you allow me to clean every part of your body with my soapy hands and fingers?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
11- How about if they like a certain sports team? 12-How about drinking too much?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
3- What’s your favorite smell? Do you a least favorite?
81~ Do you have any kinks and/or fetishes?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
3- Should Pluto still be considered a planet? 4- How about smoking?
70~ Would/do you have/like anal sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
76~ Have you had a threesome? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
18- How often do you drink alcohol? What is your favorite drink?
71~ Would you give your partner a hand or foot job? Would you receive one?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
82~ Do you have any fantasies involving Role-Playing?