What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 11:20
Do you watch it? What is your favorite?
7- What if a person smells a certain way? 8- How about smoking?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
40~ What’s the weirdest place you’ve ever had sex?
Repairman/Lonely Wife Virgin/Experienced
27- What was/ is nickname? Does it have a meaning behind it?
What have I done wrong? How can I start over?
Does the thought excite you? Care to share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Joey Chestnut, barred last July, returns to Nathan’s hot dog eating contest - The Washington Post
64~ When was your very first orgasm? When was your first from having sex? Care to share?
17- Have you ever done drugs? Which ones? How often?
83~ How do you feel about Porn?
Were any US Generals hurt or killed yesterday in Damascus, Syria, yesterday 5/9/24?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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,
US researchers solve tokamak plasma mystery with elusive ‘voids’ discovery - Interesting Engineering
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
28- What are some things that people do that irritate you?
Children of slain Minnesota lawmaker Melissa Hortman: 'We are devastated' - ABC News
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How well do you know me? And some of your thoughts about me
Should parents force their kids to go to school when they are sick?
21~ What was the best date you ever went on? What has been the worst?
What is your favorite position? Why?
What have you learned about yourself that you did not before this?
Why do older people have a hard time using technology?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
13- How about having a certain hair cut/style?
26~ What side of the bed do you sleep on?
How is sex in college like with roommates and big campuses?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
38~ Share your most embarrassing sexual memory?
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)
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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Biotech pauses trial after second patient death linked to gene therapy - The Washington Post
36~ What is your favorite time of day to have sex/make love?
How about if they talk dirty and/or call you names?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Scientists Discover Bizarre Signals Coming From Ice in Antarctica - futurism.com
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Nothing too Serious
How does a 45-year-old man get a girlfriend?
14- What's your favorite dessert? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
1~ How old were you when you had your first kiss? Who? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Why do I sweat (mostly on face) when I eat usually spicy food?
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?
If you say it, I will stop, and we can talk about it when you are ready.
51~ What tends to bring a smile to your face?
4- For a pet, Cat, dog or other?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
1- What was your first impression of me? Has it changed?
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?
2- What’s your favorite color? Do you a least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
12- What’s your favorite food? What’s your least favorite?
9- What’s your favorite season and why? What’s your least favorite?
81~ Do you have any kinks and/or fetishes?
*** Questions about Relationships/Past ***
How many partners have you had oral sex with? Who? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Do you have a favorite? Is it ok if your partner does?
45~ How do you feel about me blindfolding you? How about blindfolding me?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
50~ How many children do you have? What are their ages?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Would you ever want to be woken up with oral and/or intercourse?
19- What’s your favorite fairytale? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
11- List at least 5 things on your bucket list. Have you done any of them already?
How old are you? Male or Female?
Nurse/Patient Celebrity/Fan
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
49~ How many times have you been married? Why did they end?
33- If you could visit any time period, when would you pick? Please explain why?
*** Deal Breaker Questions ***
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?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Get this wrong and this could mean the end… :-) some funny, some not…
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Would you read them together?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
If YES, was it with 2 men or 2 women? Did you enjoy it?
13~ Is there a difference between, making love, having sex, and fucking?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
19~ Who/when was your first “heartbreak”?
Family Relation Age Play
5~ When you first started having sex, was it what you thought it would be?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
67~ Do you like it when your partner moans and/or is vocal during sex?
Would /have you ever given your partner a lap dance and Striptease?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
If yes, what?
37- Do you like your name? If you could change it, what would you change it too?
*** Random Questions ***
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
76~ Have you had a threesome? Care to Share?
*** What’s Your Favorite…? ***
20- What’s your favorite candy? What’s your least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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?
17- What’s your favorite holiday? What’s your least favorite?
89~ Do you like taking showers together?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
28~ What are some things that turn on? What is your biggest turn on?
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?
18~ Who/when was your first “crush”?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
(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…)
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…
13- What’s your favorite drink? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Have you ever? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
39~ What are your love languages?
Please share Did you stop?
That one or two things that made you go hmmmm, OMG or wow!
8- What are your thoughts on politics?
15- What's your favorite saying? What word or phrase is your least favorite?
51~ Are you willing to play adult games with your partner?
What do you dislike about me? I asked you to be 100% honest.
Do you like the “69” position? Do you prefer to be on top or bottom?
Over time has your thoughts on sex changed?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
15- What bad habit do you wish you could quit? Do you have any addictions?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Can you Deep Throat? Do you like the taste of yourself?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Teacher/Student Stranger/One Night Stand
Would you do it again, and would you rather 2 females or 2 males?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
10~ How many dates are necessary before you to have sex with someone?
82~ Do you have any fantasies involving Role-Playing?
11~ Have you ever been caught by your parents or children or others while having sex?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
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?
If you win, what will you make them do?
6- Do you have dreams? Can you remember them? What do you usually dream about?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
52~ What are your hobbies?
Prisoner/Prison Guard Landlord/Tenant
34~ Do you like the lights on or off during sex?
* Give a rating for each one (0-100)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
11- How about if they like a certain sports team? 12-How about drinking too much?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What is your favorite toy? Ever wanted to try a specific toy?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
31- If given a chance to be immortal, would you take it? Why?
52~ Are you willing to make “those types” of bets with your partner?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
8- What's your favorite flavor of ice cream? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
84~ How do you feel about reading/listening to adult stories?
13- What is the craziest/scariest thing you've ever done?
How many times do you think you have “made love”?
Any that are a turn off?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
65~ Describe the best orgasm you’ve ever had? Care to share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
71~ Would you give your partner a hand or foot job? Would you receive one?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
18- How often do you drink alcohol? What is your favorite drink?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
92~ Have you ever had or have an STD? How many? What was it?
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?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
If NO, would you ever have one? Would it be with 2 men or 2 women?
33- Beach or Mountains? Or is there another place to like better?
15~ Have you ever been “in love”? Who? Care to Share?
9- If you could have three wishes, what would they be? Why?
44~ Care to share something about yourself that no one else knows about you?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
What have you learned about me that was new and/or surprising?
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…
23- What is your dream job? What was it as a child?
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?
The Ice Breaker Questions
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
42~ What’s your biggest regret in life?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
25~ How do you feel about PDA? (Public Display of Affection)
9~ How many times over your lifetime do you think you have had sex so far?
Master/Slave Boss/Maid
34- Ever been to a concert? What was your favorite? Who would you like to see?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
What is your view on sex? Meaning, When/Where/ How often/
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
22- Do you have any birth marks? How about scars? Care to share how you got them?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
5- Have you ever been hypnotized? Would you allow yourself to be?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
47~ What would be your dream job and why?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
You know that I will be 100% truthful, so ask.
Do you think this brought you closer together?
29~ What are some things that turn you off? What is your biggest turn off?
29- How superstitious are you?
12- What is the weirdest thing you've ever eaten?
What was the longest? What was the shortest?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
70~ Would/do you have/like anal sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
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?
3- What Superhero or Superpower would you want to be/have?
Model/Photographer Police/Criminal
19- Do/have you smoked? What do you prefer? How often?
48~ Do you have any siblings? Are you close to your family?
Escort/Client Job Applicant/Hiring Manager
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
32- What's your greatest talent? Can I see it right now?
10- What is your favorite family tradition? What’s your least favorite?
61~ How willing would you be to try new sexual positions?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Would you mind if your partner watched it? How about together vs alone?
7- What are your thoughts on religion? Is there an afterlife?
*** Questions About Me ***
48~ Have you ever paid or been paid for sex?
Do you like it when they show and tell you what they want?
Will you cheat again? How can, you be sure? Define what cheating is to you.
80~ Share your top three fantasies/desires. (Be detailed) 😊
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
62~ Have you used adult toys?
What would you say to prove to yourself that it was really you?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
92~ Everyone needs a “safe” word. What is yours?
56~ Would you ever go to a strip club 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?
10- List 5 of your top pet peeves.
1- What’s your favorite animal? Do you a least favorite?
Doctor/Nurse Stripper/Client
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
21- What's your favorite way to spend a weekend or time off?
11- What's your favorite restaurant? What’s your least favorite?
30~ What's something unexpected that turns you on?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
22- What is your favorite childhood memory? What is your least favorite?
3- What’s your favorite smell? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
I would allow you to do it… What would you do to me?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?