What is the most interesting question you can ask to get to know someone?
Last Updated: 16.06.2025 05:15
48~ Do you have any siblings? Are you close to your family?
Do you think this brought you closer together?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Do happily married husbands cheat?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What are some cool confidence hacks?
5- Have you ever been hypnotized? Would you allow yourself to be?
9- Is there something you’ve always wanted to ask me but you’re afraid?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
9~ How many times over your lifetime do you think you have had sex so far?
Nurse/Patient Celebrity/Fan
If YES, was it with 2 men or 2 women? Did you enjoy it?
21- What's your favorite way to spend a weekend or time off?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Over time has your thoughts on sex changed?
Is it recommended to leave a note in a lost wallet asking for it to be returned?
Any that are a turn off?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
14- What is an embarrassing moment in your life? How about your most embarrassing?
45~ How do you feel about me blindfolding you? How about blindfolding me?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Get this wrong and this could mean the end… :-) some funny, some not…
What made you feel disgusted today?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Would you ever want to be woken up with oral and/or intercourse?
Do you like the “69” position? Do you prefer to be on top or bottom?
First quantum-mechanical model of quasicrystals reveals why they exist - Phys.org
19~ Who/when was your first “heartbreak”?
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
What is the rudest/meanest thing a family member has said to you?
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)
76~ Have you had a threesome? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?
What’s the saddest thing you’ve seen at your job?
82~ Do you have any fantasies involving Role-Playing?
*** What’s Your Favorite…? ***
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
1- What was your first impression of me? Has it changed?
18- How often do you drink alcohol? What is your favorite drink?
Is it true that Jehovah's witnesses once thought the world would end in 1975?
92~ Everyone needs a “safe” word. What is yours?
61~ How willing would you be to try new sexual positions?
What would you say to prove to yourself that it was really you?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
21~ What was the best date you ever went on? What has been the worst?
*** Questions About Me ***
17- Have you ever done drugs? Which ones? How often?
36- Do you play video games? What is your favorite? Do you a least favorite?
28- What are some things that people do that irritate you?
11- List at least 5 things on your bucket list. Have you done any of them already?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
51~ What tends to bring a smile to your face?
8- What's your favorite flavor of ice cream? Do you a least favorite?
31- If given a chance to be immortal, would you take it? Why?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
44~ Care to share something about yourself that no one else knows about you?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
7- What are your thoughts on religion? Is there an afterlife?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
I would allow you to do it… What would you do to me?
(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…)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
7- What if a person smells a certain way? 8- How about smoking?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
29~ What are some things that turn you off? What is your biggest turn off?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
84~ How do you feel about reading/listening to adult stories?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Nothing too Serious
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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…
5~ When you first started having sex, was it what you thought it would be?
10- List 5 of your top pet peeves.
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?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
36~ What is your favorite time of day to have sex/make love?
81~ Do you have any kinks and/or fetishes?
12- What is the weirdest thing you've ever eaten?
67~ Do you like it when your partner moans and/or is vocal during sex?
How well do you know me? And some of your thoughts about me
13- What is the craziest/scariest thing you've ever done?
Prisoner/Prison Guard Landlord/Tenant
28~ What are some things that turn on? What is your biggest turn on?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you watch it? What is your favorite?
62~ Have you used adult toys?
26~ What side of the bed do you sleep on?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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 position? Why?
52~ Are you willing to make “those types” of bets with your partner?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
38~ Share your most embarrassing sexual memory?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
* Give a rating for each one (0-100)
33- If you could visit any time period, when would you pick? Please explain why?
That one or two things that made you go hmmmm, OMG or wow!
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…
50~ How many children do you have? What are their ages?
If you say it, I will stop, and we can talk about it when you are ready.
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
If NO, would you ever have one? Would it be with 2 men or 2 women?
70~ Would/do you have/like anal sex?
Repairman/Lonely Wife Virgin/Experienced
83~ How do you feel about Porn?
7-What do I do in bed that drives you wild? How about, what turns you off?
11- How about if they like a certain sports team? 12-How about drinking too much?
48~ Have you ever paid or been paid for sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
What is your favorite toy? Ever wanted to try a specific toy?
9- What’s your favorite season and why? What’s your least favorite?
47~ What would be your dream job and why?
8- What are your thoughts on politics?
3- What Superhero or Superpower would you want to be/have?
If you win, what will you make them do?
Please share Did you stop?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
49~ How many times have you been married? Why did they end?
Any that are a turn off?
The Ice Breaker Questions
42~ What’s your biggest regret in life?
92~ Have you ever had or have an STD? How many? What was it?
What have you learned about me that was new and/or surprising?
52~ What are your hobbies?
You know that I will be 100% truthful, so ask.
3- What’s your favorite smell? Do you a least favorite?
What have you learned about yourself that you did not before this?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
*** Deal Breaker Questions ***
What was the longest? What was the shortest?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
18~ Who/when was your first “crush”?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
19- Do/have you smoked? What do you prefer? How often?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Master/Slave Boss/Maid
What do you dislike about me? I asked you to be 100% honest.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
89~ Do you like taking showers together?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
How old are you? Male or Female?
22- What is your favorite childhood memory? What is your least favorite?
Have you ever? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
*** Questions about Relationships/Past ***
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
29- How superstitious are you?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
6- Do you have dreams? Can you remember them? What do you usually dream about?
25~ How do you feel about PDA? (Public Display of Affection)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Family Relation Age Play
22~ What is the best pickup line anyone has ever used on you? What was the worst?
80~ Share your top three fantasies/desires. (Be detailed) 😊
14- What's your favorite dessert? Do you a least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
22- Do you have any birth marks? How about scars? Care to share how you got them?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
How many times do you think you have “made love”?
13~ Is there a difference between, making love, having sex, and fucking?
What is your view on sex? Meaning, When/Where/ How often/
Would you read them together?
23- What is your dream job? What was it as a child?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Does the thought excite you? Care to share?
65~ Describe the best orgasm you’ve ever had? Care to share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would /have you ever given your partner a lap dance and Striptease?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
51~ Are you willing to play adult games with your partner?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Would you do it again, and would you rather 2 females or 2 males?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Doctor/Nurse Stripper/Client
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
10~ How many dates are necessary before you to have sex with someone?
Escort/Client Job Applicant/Hiring Manager
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
12- What’s your favorite food? What’s your least favorite?
Would you mind if your partner watched it? How about together vs alone?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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?
39~ What are your love languages?
32- What's your greatest talent? Can I see it right now?
1~ How old were you when you had your first kiss? Who? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
71~ Would you give your partner a hand or foot job? Would you receive one?
17- What’s your favorite holiday? What’s your least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
4- For a pet, Cat, dog or other?
37- Do you like your name? If you could change it, what would you change it too?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
13- How about having a certain hair cut/style?
1- What’s your favorite animal? Do you a least favorite?
34~ Do you like the lights on or off during sex?
Model/Photographer Police/Criminal
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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,
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
20- Do you have any tattoos? 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?
13- What’s your favorite drink? What’s your least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
10- What is your favorite family tradition? What’s your least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
2- What’s your favorite color? Do you a least favorite?
Teacher/Student Stranger/One Night Stand
9- If you could have three wishes, what would they be? Why?
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?
27- What was/ is nickname? Does it have a meaning behind it?
30~ What's something unexpected that turns you on?
Do you like it when they show and tell you what they want?
Would you allow me to clean every part of your body with my soapy hands and fingers?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
20- What’s your favorite candy? What’s your least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
If yes, what?
How many partners have you had oral sex with? Who? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Will you cheat again? How can, you be sure? Define what cheating is to you.
33- Beach or Mountains? Or is there another place to like better?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
How about if they talk dirty and/or call you names?
*** Random Questions ***
11- What's your favorite restaurant? What’s your least favorite?