What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 01:39
49~ How many times have you been married? Why did they end?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
12- What is the weirdest thing you've ever eaten?
30~ What's something unexpected that turns you on?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
How do you feel about Donald Trump signing an executive order that says there are only two genders?
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?
Would you do it again, and would you rather 2 females or 2 males?
Model/Photographer Police/Criminal
Is it possible to achieve spiritual enlightenment while being in a romantic relationship?
65~ Describe the best orgasm you’ve ever had? Care to share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
76~ Have you had a threesome? Care to Share?
What is your review of House of the Dragon Season 2 finale, Episode 8?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
70~ Would/do you have/like anal sex?
Nurse/Patient Celebrity/Fan
Gucci Owner Picks Auto Executive for One of Global Luxury’s Top Jobs - WSJ
18~ Who/when was your first “crush”?
25~ How do you feel about PDA? (Public Display of Affection)
22- What is your favorite childhood memory? What is your least favorite?
Do very hot men ever feel attracted to an ugly woman? Why?
* Give a rating for each one (0-100)
31- If given a chance to be immortal, would you take it? Why?
I would allow you to do it… What would you do to me?
Why do females hate MGTOW so much?
*** Deal Breaker Questions ***
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Why would an older small breed dog become obsessive about hygiene?
11~ Have you ever been caught by your parents or children or others while having sex?
Would /have you ever given your partner a lap dance and Striptease?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
When you visit a store, do you go to shop or buy?
Would you allow me to clean every part of your body with my soapy hands and fingers?
If yes, what?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How do I identify fake friends in life?
21- What's your favorite way to spend a weekend or time off?
48~ Do you have any siblings? Are you close to your family?
20- What’s your favorite candy? What’s your least favorite?
What was the longest? What was the shortest?
Any that are a turn off?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
7- What if a person smells a certain way? 8- How about smoking?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Have you ever been humiliated in front of a group of girls and enjoyed it?
15- What bad habit do you wish you could quit? Do you have any addictions?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
61~ How willing would you be to try new sexual positions?
Do Republicans give permission to Democrats to vote for any candidate except for Kamala Harris?
*** Random Questions ***
Can you Deep Throat? Do you like the taste of yourself?
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?
83~ How do you feel about Porn?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
29~ What are some things that turn you off? What is your biggest turn off?
Do you like it when they show and tell you what they want?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
How many partners have you had oral sex with? Who? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
* 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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
*** What’s Your Favorite…? ***
32- What's your greatest talent? Can I see it right now?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
37- Do you like your name? If you could change it, what would you change it too?
5- Have you ever been hypnotized? Would you allow yourself to be?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
52~ Are you willing to make “those types” of bets with your partner?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
The Ice Breaker Questions
1- What’s your favorite animal? Do you a least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Would you mind if your partner watched it? How about together vs alone?
Do you like the “69” position? Do you prefer to be on top or bottom?
82~ Do you have any fantasies involving Role-Playing?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Teacher/Student Stranger/One Night Stand
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
10- List 5 of your top pet peeves.
34- Ever been to a concert? What was your favorite? Who would you like to see?
10- What is your favorite family tradition? What’s your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Would you ever want to be woken up with oral and/or intercourse?
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Does the thought excite you? Care to share?
What is your view on sex? Meaning, When/Where/ How often/
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What would you say to prove to yourself that it was really you?
What do you dislike about me? I asked you to be 100% honest.
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
81~ Do you have any kinks and/or fetishes?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
11- What's your favorite restaurant? What’s your least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
3- What Superhero or Superpower would you want to be/have?
39~ What are your love languages?
That one or two things that made you go hmmmm, OMG or wow!
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?
Escort/Client Job Applicant/Hiring Manager
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
13- How about having a certain hair cut/style?
15- What's your favorite saying? What word or phrase is your least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
18- How often do you drink alcohol? What is your favorite drink?
33- Beach or Mountains? Or is there another place to like better?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Would you read them together?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
*** Questions about Relationships/Past ***
What have you learned about me that was new and/or surprising?
Over time has your thoughts on sex changed?
11- List at least 5 things on your bucket list. Have you done any of them already?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
1- What was your first impression of me? Has it changed?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
9- Is there something you’ve always wanted to ask me but you’re afraid?
17- What’s your favorite holiday? What’s your least favorite?
44~ Care to share something about yourself that no one else knows about you?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
26~ What side of the bed do you sleep on?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
92~ Have you ever had or have an STD? How many? What was it?
13- What’s your favorite drink? What’s your least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
48~ Have you ever paid or been paid for sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
3- Should Pluto still be considered a planet? 4- How about smoking?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
28~ What are some things that turn on? What is your biggest turn on?
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?
9- If you could have three wishes, what would they be? Why?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
71~ Would you give your partner a hand or foot job? Would you receive one?
33- If you could visit any time period, when would you pick? Please explain why?
Master/Slave Boss/Maid
51~ What tends to bring a smile to your face?
1~ How old were you when you had your first kiss? Who? Care to Share?
84~ How do you feel about reading/listening to adult stories?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
10~ How many dates are necessary before you to have sex with someone?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
What have you learned about yourself that you did not before this?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
28- What are some things that people do that irritate you?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
(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…)
Do you have a favorite? Is it ok if your partner does?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
13- What is the craziest/scariest thing you've ever done?
92~ Everyone needs a “safe” word. What is yours?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Family Relation Age Play
If YES, was it with 2 men or 2 women? Did you enjoy it?
Doctor/Nurse Stripper/Client
24~ What are your expectations in a relationship? (I know a very big question, take your time)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
11- How about if they like a certain sports team? 12-How about drinking too much?
Nothing too Serious
12- What’s your favorite food? What’s your least favorite?
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?
5~ When you first started having sex, was it what you thought it would be?
50~ How many children do you have? What are their ages?
If NO, would you ever have one? Would it be with 2 men or 2 women?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
19- What’s your favorite fairytale? What’s your least favorite?
You know that I will be 100% truthful, so ask.
36~ What is your favorite time of day to have sex/make love?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
89~ Do you like taking showers together?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
4- For a pet, Cat, dog or other?
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What is your favorite position? Why?
6- Do you have dreams? Can you remember them? What do you usually dream about?
67~ Do you like it when your partner moans and/or is vocal during sex?
What is your favorite toy? Ever wanted to try a specific toy?
47~ What would be your dream job and why?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
19- Do/have you smoked? What do you prefer? How often?
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,
Prisoner/Prison Guard Landlord/Tenant
Do you think this brought you closer together?
51~ Are you willing to play adult games with your partner?
9- What’s your favorite season and why? What’s your least favorite?
How about if they talk dirty and/or call you names?
23- What is your dream job? What was it as a child?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
13~ Is there a difference between, making love, having sex, and fucking?
Any that are a turn off?
If you say it, I will stop, and we can talk about it when you are ready.
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Please share Did you stop?
22- Do you have any birth marks? How about scars? Care to share how you got them?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Repairman/Lonely Wife Virgin/Experienced
53~ How much can you tell me about the one thing you are most passionate about?
52~ What are your hobbies?
17- Have you ever done drugs? Which ones? How often?
*** Questions About Me ***
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…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
7-What do I do in bed that drives you wild? How about, what turns you off?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
How old are you? Male or Female?
29- How superstitious are you?
19~ Who/when was your first “heartbreak”?
9~ How many times over your lifetime do you think you have had sex so far?
42~ What’s your biggest regret in life?
Do you watch it? What is your favorite?
15~ Have you ever been “in love”? Who? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
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?
How many times do you think you have “made love”?
38~ Share your most embarrassing sexual memory?
27- What was/ is nickname? Does it have a meaning behind it?
Have you ever? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
21~ What was the best date you ever went on? What has been the worst?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Will you cheat again? How can, you be sure? Define what cheating is to you.
If you win, what will you make them do?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
34~ Do you like the lights on or off during sex?
How well do you know me? And some of your thoughts about me
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
36- Do you play video games? What is your favorite? Do you a least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
8- What are your thoughts on politics?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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…
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
14- What's your favorite dessert? Do you a least favorite?
2- What’s your favorite color? Do you a least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
62~ Have you used adult toys?
7- What are your thoughts on religion? Is there an afterlife?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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)