What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 06:08
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Which one is better to guys, boobs or butt?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Have you ever forcibly sucked someone’s dick?
29- How superstitious are you?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
How could Trump, with his deplorable garbage supporters, manage to win an election?
36~ What is your favorite time of day to have sex/make love?
11- List at least 5 things on your bucket list. Have you done any of them already?
15- What's your favorite saying? What word or phrase is your least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
21- What's your favorite way to spend a weekend or time off?
That one or two things that made you go hmmmm, OMG or wow!
How do you get a girl to like you?
42~ What’s your biggest regret in life?
22- Do you have any birth marks? How about scars? Care to share how you got them?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Why is Taylor Swift re-recording her albums?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
7- What are your thoughts on religion? Is there an afterlife?
40~ What’s the weirdest place you’ve ever had sex?
Can a Trump supporter explain what was wrong with what Bishop Budde said to Donald Trump?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Why don't we hear our own snoring?
Any that are a turn off?
If yes, what?
Nurse/Patient Celebrity/Fan
If gays can get married, why can't I marry my dog or a cheeseburger?
31- If given a chance to be immortal, would you take it? Why?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Can you Deep Throat? Do you like the taste of yourself?
Why should we share our wife with others?
*** Random Questions ***
28- What are some things that people do that irritate you?
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?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
5- Have you ever been hypnotized? Would you allow yourself to be?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Have you ever dealt with a Christian narcissist?
10- What is your favorite family tradition? What’s your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Please share Did you stop?
5 Simple Walking Tricks That Burn Fat and Build Muscle, According to a Trainer - Eat This Not That
62~ Have you used adult toys?
81~ Do you have any kinks and/or fetishes?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
How do I become an intelligent man?
What have you learned about me that was new and/or surprising?
32- What's your greatest talent? Can I see it right now?
If you say it, I will stop, and we can talk about it when you are ready.
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…
36- Do you play video games? What is your favorite? Do you a least favorite?
Doctor/Nurse Stripper/Client
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
*** Deal Breaker Questions ***
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
(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…)
Would you do it again, and would you rather 2 females or 2 males?
Get this wrong and this could mean the end… :-) some funny, some not…
26~ What side of the bed do you sleep on?
Do you have a favorite? Is it ok if your partner does?
*** What’s Your Favorite…? ***
11~ Have you ever been caught by your parents or children or others while having sex?
52~ What are your hobbies?
18~ Who/when was your first “crush”?
19~ Who/when was your first “heartbreak”?
47~ What would be your dream job and why?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
22- What is your favorite childhood memory? What is your least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Nothing too Serious
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What is your view on sex? Meaning, When/Where/ How often/
5~ When you first started having sex, was it what you thought it would be?
44~ Care to share something about yourself that no one else knows about you?
Teacher/Student Stranger/One Night Stand
Will you cheat again? How can, you be sure? Define what cheating is to you.
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
2- What’s your favorite color? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
34~ Do you like the lights on or off during sex?
1- What’s your favorite animal? Do you a least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
What do you dislike about me? I asked you to be 100% honest.
45~ How do you feel about me blindfolding you? How about blindfolding me?
13~ Is there a difference between, making love, having sex, and fucking?
33- If you could visit any time period, when would you pick? Please explain why?
27- What was/ is nickname? Does it have a meaning behind it?
25~ How do you feel about PDA? (Public Display of Affection)
Model/Photographer Police/Criminal
48~ Have you ever paid or been paid for sex?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
83~ How do you feel about Porn?
8- What are your thoughts on politics?
Would you mind if your partner watched it? How about together vs alone?
39~ What are your love languages?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
What was the longest? What was the shortest?
11- How about if they like a certain sports team? 12-How about drinking too much?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
19- What’s your favorite fairytale? What’s your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
12- What’s your favorite food? What’s your least favorite?
9- If you could have three wishes, what would they be? Why?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
53~ How much can you tell me about the one thing you are most passionate about?
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?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Have you ever? Care to Share?
If you win, what will you make them do?
4- For a pet, Cat, dog or other?
15~ Have you ever been “in love”? Who? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
How about if they talk dirty and/or call you names?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Do you like it when they show and tell you what they want?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
10~ How many dates are necessary before you to have sex with someone?
7- What if a person smells a certain way? 8- How about smoking?
* Give a rating for each one (0-100)
49~ How many times have you been married? Why did they end?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
9- What’s your favorite season and why? What’s your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
3- What’s your favorite smell? Do you a least favorite?
51~ What tends to bring a smile to your face?
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?
19- Do/have you smoked? What do you prefer? How often?
Repairman/Lonely Wife Virgin/Experienced
How well do you know me? And some of your thoughts about me
92~ Have you ever had or have an STD? How many? What was it?
15- What bad habit do you wish you could quit? Do you have any addictions?
20- What’s your favorite candy? What’s your least favorite?
11- What's your favorite restaurant? What’s your least favorite?
What is your favorite position? Why?
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…
If you lose, are you willing to be their sex slave for a day, (anything goes)?
33- Beach or Mountains? Or is there another place to like better?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How many times do you think you have “made love”?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
65~ Describe the best orgasm you’ve ever had? Care to share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
21~ What was the best date you ever went on? What has been the worst?
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
76~ Have you had a threesome? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Do you watch it? What is your favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What is your favorite toy? Ever wanted to try a specific toy?
92~ Everyone needs a “safe” word. What is yours?
1~ How old were you when you had your first kiss? Who? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
14- What's your favorite dessert? Do you a least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
8- What's your favorite flavor of ice cream? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
Over time has your thoughts on sex changed?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
30~ What's something unexpected that turns you on?
61~ How willing would you be to try new sexual positions?
How many partners have you had oral sex with? Who? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
6- Do you have dreams? Can you remember them? What do you usually dream about?
I would allow you to do it… What would you do to me?
Family Relation Age Play
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
17- Have you ever done drugs? Which ones? How often?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
17- What’s your favorite holiday? What’s your least favorite?
What would you say to prove to yourself that it was really you?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
51~ Are you willing to play adult games with your partner?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3- What Superhero or Superpower would you want to be/have?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
23- What is your dream job? What was it as a child?
13- What is the craziest/scariest thing you've ever done?
*** Questions About Me ***
Do you think this brought you closer together?
You know that I will be 100% truthful, so ask.
13- How about having a certain hair cut/style?
1- What was your first impression of me? Has it changed?
14- What is an embarrassing moment in your life? How about your most embarrassing?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
18- How often do you drink alcohol? What is your favorite drink?
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?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
89~ Do you like taking showers together?
82~ Do you have any fantasies involving Role-Playing?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
10- List 5 of your top pet peeves.
If NO, would you ever have one? Would it be with 2 men or 2 women?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
29~ What are some things that turn you off? What is your biggest turn off?
Does the thought excite you? Care to share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
7-What do I do in bed that drives you wild? How about, what turns you off?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How old are you? Male or Female?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
12- What is the weirdest thing you've ever eaten?
Master/Slave Boss/Maid
70~ Would/do you have/like anal sex?
67~ Do you like it when your partner moans and/or is vocal during sex?
*** Questions about Relationships/Past ***
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)
38~ Share your most embarrassing sexual memory?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
34- Ever been to a concert? What was your favorite? Who would you like to see?
Would /have you ever given your partner a lap dance and Striptease?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Would you read them together?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
48~ Do you have any siblings? Are you close to your family?
The Ice Breaker Questions
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Prisoner/Prison Guard Landlord/Tenant
64~ When was your very first orgasm? When was your first from having sex? Care to share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Any that are a turn off?
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,
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What have you learned about yourself that you did not before this?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
50~ How many children do you have? What are their ages?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
3- Should Pluto still be considered a planet? 4- How about smoking?
28~ What are some things that turn on? What is your biggest turn on?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
13- What’s your favorite drink? What’s your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would you ever want to be woken up with oral and/or intercourse?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Escort/Client Job Applicant/Hiring Manager