What is the most interesting question you can ask to get to know someone?
Last Updated: 27.06.2025 03:48
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
1- What’s your favorite animal? Do you a least favorite?
36~ What is your favorite time of day to have sex/make love?
Temu’s daily US users cut in half following end of ‘de minimis’ loophole - New York Post
17- What’s your favorite holiday? What’s your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
14,000-year-old mummified ‘puppies’ weren’t dogs at all, new research shows - CNN
11- How about if they like a certain sports team? 12-How about drinking too much?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Are there girls here who like group sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What have you learned about me that was new and/or surprising?
15- What bad habit do you wish you could quit? Do you have any addictions?
Drinking coffee could help you age better, according to this Harvard study. - Stewartville Star
If NO, would you ever have one? Would it be with 2 men or 2 women?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Have you ever? Care to Share?
What is your review of working in EY?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Get this wrong and this could mean the end… :-) some funny, some not…
53~ How much can you tell me about the one thing you are most passionate about?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
28- What are some things that people do that irritate you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Craig admits to 'illegal move' in controversial 'no contest' - BBC
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Do you have a favorite? Is it ok if your partner does?
Would you mind if your partner watched it? How about together vs alone?
King Charles praised for 'faultless' firing technique at Larkhill - BBC
Teacher/Student Stranger/One Night Stand
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
9- If you could have three wishes, what would they be? Why?
Deportees are being held in a converted shipping container in Djibouti, ICE says - NPR
Please share Did you stop?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Repairman/Lonely Wife Virgin/Experienced
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
67~ Do you like it when your partner moans and/or is vocal during sex?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
19- Do/have you smoked? What do you prefer? How often?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
44~ Care to share something about yourself that no one else knows about you?
32- What's your greatest talent? Can I see it right now?
10- What is your favorite family tradition? What’s your least favorite?
50~ How many children do you have? What are their ages?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
19- What’s your favorite fairytale? What’s your least favorite?
If you win, what will you make them do?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Would you read them together?
7- What if a person smells a certain way? 8- How about smoking?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Would /have you ever given your partner a lap dance and Striptease?
51~ Are you willing to play adult games with your partner?
5- Have you ever been hypnotized? Would you allow yourself to be?
82~ Do you have any fantasies involving Role-Playing?
18~ Who/when was your first “crush”?
How about if they talk dirty and/or call you names?
71~ Would you give your partner a hand or foot job? Would you receive one?
11- List at least 5 things on your bucket list. Have you done any of them already?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How many times do you think you have “made love”?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
13- What’s your favorite drink? What’s your least favorite?
2- What’s your favorite color? Do you a least favorite?
Doctor/Nurse Stripper/Client
31- If given a chance to be immortal, would you take it? Why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
12- What is the weirdest thing you've ever eaten?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
If YES, was it with 2 men or 2 women? Did you enjoy it?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
1- What was your first impression of me? Has it changed?
33- If you could visit any time period, when would you pick? Please explain why?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Over time has your thoughts on sex changed?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
13- What is the craziest/scariest thing you've ever done?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
52~ Are you willing to make “those types” of bets with your partner?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you watch it? What is your 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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
What have you learned about yourself that you did not before this?
11- What's your favorite restaurant? What’s your least favorite?
How well do you know me? And some of your thoughts about me
*** Random Questions ***
Would you ever want to be woken up with oral and/or intercourse?
How many partners have you had oral sex with? Who? Care to Share?
17- Have you ever done drugs? Which ones? How often?
9- What’s your favorite season and why? What’s your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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,
What do you dislike about me? I asked you to be 100% honest.
22- What is your favorite childhood memory? What is your least favorite?
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?
39~ What are your love languages?
3- What Superhero or Superpower would you want to be/have?
26~ What side of the bed do you sleep on?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
84~ How do you feel about reading/listening to adult stories?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
19~ Who/when was your first “heartbreak”?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
Would you allow me to clean every part of your body with my soapy hands and fingers?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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?
14- What's your favorite dessert? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
21~ What was the best date you ever went on? What has been the worst?
You know that I will be 100% truthful, so ask.
*** Deal Breaker Questions ***
If yes, what?
28~ What are some things that turn on? What is your biggest turn on?
How old are you? Male or Female?
15- What's your favorite saying? What word or phrase is your least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
I would allow you to do it… What would you do to me?
33- Beach or Mountains? Or is there another place to like better?
36- Do you play video games? What is your favorite? Do you a least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
34- Ever been to a concert? What was your favorite? Who would you like to see?
6- Do you have dreams? Can you remember them? What do you usually dream about?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
61~ How willing would you be to try new sexual positions?
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…
*** What’s Your Favorite…? ***
89~ Do you like taking showers together?
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Can you Deep Throat? Do you like the taste of yourself?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
*** Questions about Relationships/Past ***
20- What’s your favorite candy? What’s your least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
18- How often do you drink alcohol? What is your favorite drink?
83~ How do you feel about Porn?
7- What are your thoughts on religion? Is there an afterlife?
What is your view on sex? Meaning, When/Where/ How often/
27- What was/ is nickname? Does it have a meaning behind it?
29- How superstitious are you?
What would you say to prove to yourself that it was really you?
Family Relation Age Play
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Do you like the “69” position? Do you prefer to be on top or bottom?
62~ Have you used adult toys?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What is your favorite position? Why?
Do you like it when they show and tell you what they want?
If you say it, I will stop, and we can talk about it when you are ready.
13- How about having a certain hair cut/style?
12- What’s your favorite food? What’s your least favorite?
What was the longest? What was the shortest?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Master/Slave Boss/Maid
48~ Do you have any siblings? Are you close to your family?
68~ Would you ever get your partner up from bed by using oral sex 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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
1~ How old were you when you had your first kiss? Who? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
47~ What would be your dream job and why?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
48~ Have you ever paid or been paid for sex?
Will you cheat again? How can, you be sure? Define what cheating is to you.
10- List 5 of your top pet peeves.
Would you do it again, and would you rather 2 females or 2 males?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Any that are a turn off?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Prisoner/Prison Guard Landlord/Tenant
49~ If you could, would you want to be the opposite sex for a day, week, or year?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
Nurse/Patient Celebrity/Fan
52~ What are your hobbies?
Nothing too Serious
Any that are a turn off?
34~ Do you like the lights on or off during sex?
*** Questions About Me ***
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Escort/Client Job Applicant/Hiring Manager
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
70~ Would/do you have/like anal sex?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
(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…)
8- What are your thoughts on politics?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
15~ Have you ever been “in love”? Who? Care to Share?
23- What is your dream job? What was it as a child?
5~ When you first started having sex, was it what you thought it would be?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
55~ Would you ever go to a nude beach/resort 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?
What is your favorite toy? Ever wanted to try a specific toy?
22- Do you have any birth marks? How about scars? Care to share how you got them?
40~ What’s the weirdest place you’ve ever had sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Do you think this brought you closer together?
42~ What’s your biggest regret in life?
Model/Photographer Police/Criminal
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
The Ice Breaker Questions
38~ Share your most embarrassing sexual memory?
30~ What's something unexpected that turns you on?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
10~ How many dates are necessary before you to have sex with someone?
51~ What tends to bring a smile to your face?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
49~ How many times have you been married? Why did they end?
* Give a rating for each one (0-100)
60~ How important is oral sex? Do you like receiving? Do you like giving?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
That one or two things that made you go hmmmm, OMG or wow!
21- What's your favorite way to spend a weekend or time off?
4- For a pet, Cat, dog or other?
29~ What are some things that turn you off? What is your biggest turn off?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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)
Does the thought excite you? Care to share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
65~ Describe the best orgasm you’ve ever had? Care to share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
37- Do you like your name? If you could change it, what would you change it too?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
76~ Have you had a threesome? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
11~ Have you ever been caught by your parents or children or others while having sex?
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…
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3- What’s your favorite smell? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
92~ Everyone needs a “safe” word. What is yours?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
7-What do I do in bed that drives you wild? How about, what turns you off?
81~ Do you have any kinks and/or fetishes?
25~ How do you feel about PDA? (Public Display of Affection)