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