What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 09:01
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
27- What was/ is nickname? Does it have a meaning behind it?
Do women like watching men sucking men?
2- What’s your favorite color? Do you a least favorite?
1- What’s your favorite animal? Do you a least favorite?
*** Random Questions ***
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
39~ What are your love languages?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Do you agree with Kamala Harris that Donald Trump is dangerous?
83~ How do you feel about Porn?
44~ Care to share something about yourself that no one else knows about you?
15- What bad habit do you wish you could quit? Do you have any addictions?
What was your first trans experience like?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
92~ Have you ever had or have an STD? How many? What was it?
Get this wrong and this could mean the end… :-) some funny, some not…
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
What is your favorite position? Why?
7- What if a person smells a certain way? 8- How about smoking?
I dreamt my mother had died and I cried so much in my dream. What does it mean?
36- Do you play video games? What is your favorite? Do you a least favorite?
18- How often do you drink alcohol? What is your favorite drink?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
33- Beach or Mountains? Or is there another place to like better?
28~ What are some things that turn on? What is your biggest turn on?
Is it sinful for Christians to look at beautiful women?
49~ How many times have you been married? Why did they end?
71~ Would you give your partner a hand or foot job? Would you receive one?
Model/Photographer Police/Criminal
Why are Republicans such intolerant people?
19- What’s your favorite fairytale? What’s your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
What do you dislike about me? I asked you to be 100% honest.
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
The Ice Breaker Questions
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
9- What’s your favorite season and why? What’s your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
51~ What tends to bring a smile to your face?
62~ Have you used adult toys?
60~ How important is oral sex? Do you like receiving? Do you like giving?
81~ Do you have any kinks and/or fetishes?
14- What is an embarrassing moment in your life? How about your most embarrassing?
How many times do you think you have “made love”?
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?
Would you allow me to clean every part of your body with my soapy hands and fingers?
8- What are your thoughts on politics?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Nurse/Patient Celebrity/Fan
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What was the longest? What was the shortest?
37- Do you like your name? If you could change it, what would you change it too?
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?
53~ How much can you tell me about the one thing you are most passionate about?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
If you say it, I will stop, and we can talk about it when you are ready.
Repairman/Lonely Wife Virgin/Experienced
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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
18~ Who/when was your first “crush”?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
If YES, was it with 2 men or 2 women? Did you enjoy it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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…
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Do you watch it? What is your favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
67~ Do you like it when your partner moans and/or is vocal during sex?
61~ How willing would you be to try new sexual positions?
76~ Have you had a threesome? Care to Share?
Doctor/Nurse Stripper/Client
3- What Superhero or Superpower would you want to be/have?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
7-What do I do in bed that drives you wild? How about, what turns you off?
Does the thought excite you? Care to share?
Nothing too Serious
Over time has your thoughts on sex changed?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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)?
Would you mind if your partner watched it? How about together vs alone?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
That one or two things that made you go hmmmm, OMG or wow!
15~ Have you ever been “in love”? Who? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
10- List 5 of your top pet peeves.
5~ When you first started having sex, was it what you thought it would be?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Would you ever want to be woken up with oral and/or intercourse?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
42~ What’s your biggest regret in life?
What would you say to prove to yourself that it was really you?
10- What is your favorite family tradition? What’s your least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Master/Slave Boss/Maid
13~ Is there a difference between, making love, having sex, and fucking?
3- What’s your favorite smell? Do you a least favorite?
Teacher/Student Stranger/One Night Stand
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Have you ever? Care to Share?
5- Have you ever been hypnotized? Would you allow yourself to be?
92~ Everyone needs a “safe” word. What is yours?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
If you win, what will you make them do?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
21- What's your favorite way to spend a weekend or time off?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
47~ What would be your dream job and why?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
38~ Share your most embarrassing sexual memory?
15- What's your favorite saying? What word or phrase is your least favorite?
How old are you? Male or Female?
7- What are your thoughts on religion? Is there an afterlife?
84~ How do you feel about reading/listening to adult stories?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
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)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
13- How about having a certain hair cut/style?
Would you read them together?
19~ Who/when was your first “heartbreak”?
21~ What was the best date you ever went on? What has been the worst?
6- Do you have dreams? Can you remember them? What do you usually dream about?
11- List at least 5 things on your bucket list. Have you done any of them already?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
33- If you could visit any time period, when would you pick? Please explain why?
34~ Do you like the lights on or off during sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
13- What’s your favorite drink? What’s your least favorite?
(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…)
11- How about if they like a certain sports team? 12-How about drinking too much?
12- What’s your favorite food? What’s your least favorite?
How well do you know me? And some of your thoughts about me
36~ What is your favorite time of day to have sex/make love?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
1- What was your first impression of me? Has it changed?
Any that are a turn off?
What is your favorite toy? Ever wanted to try a specific toy?
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,
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
4- For a pet, Cat, dog or other?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
What have you learned about me that was new and/or surprising?
23- What is your dream job? What was it as a child?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
29- How superstitious are you?
48~ Do you have any siblings? Are you close to your family?
70~ Would/do you have/like anal sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
11- What's your favorite restaurant? What’s your least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
29~ What are some things that turn you off? What is your biggest turn off?
9- Is there something you’ve always wanted to ask me but you’re afraid?
*** Deal Breaker Questions ***
19- Do/have you smoked? What do you prefer? How often?
80~ Share your top three fantasies/desires. (Be detailed) 😊
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Any that are a turn off?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
12- What is the weirdest thing you've ever eaten?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What is your view on sex? Meaning, When/Where/ How often/
45~ How do you feel about me blindfolding you? How about blindfolding me?
If yes, what?
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 have you learned about yourself that you did not before this?
Family Relation Age Play
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
51~ Are you willing to play adult games with your partner?
How many partners have you had oral sex with? Who? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
25~ How do you feel about PDA? (Public Display of Affection)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
How about if they talk dirty and/or call you names?
26~ What side of the bed do you sleep on?
*** What’s Your Favorite…? ***
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Escort/Client Job Applicant/Hiring Manager
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?
13- What is the craziest/scariest thing you've ever done?
10~ How many dates are necessary before you to have sex with someone?
82~ Do you have any fantasies involving Role-Playing?
*** Questions About Me ***
If NO, would you ever have one? Would it be with 2 men or 2 women?
31- If given a chance to be immortal, would you take it? Why?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
*** Questions about Relationships/Past ***
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Please share Did you stop?
30~ What's something unexpected that turns you on?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Can you Deep Throat? Do you like the taste of yourself?
17- Have you ever done drugs? Which ones? How often?
Do you like it when they show and tell you what they want?
14- What's your favorite dessert? Do you a least favorite?
Do you think this brought you closer together?
You know that I will be 100% truthful, so ask.
48~ Have you ever paid or been paid for sex?
52~ What are your hobbies?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
* Give a rating for each one (0-100)
32- What's your greatest talent? Can I see it right now?
28- What are some things that people do that irritate you?
Would /have you ever given your partner a lap dance and Striptease?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Do you like the “69” position? Do you prefer to be on top or bottom?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
40~ What’s the weirdest place you’ve ever had sex?
9- If you could have three wishes, what would they be? Why?
17- What’s your favorite holiday? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
22- What is your favorite childhood memory? What is your least favorite?
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…
I would allow you to do it… What would you do to me?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
52~ Are you willing to make “those types” of bets with your partner?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
89~ Do you like taking showers together?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
50~ How many children do you have? What are their ages?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Prisoner/Prison Guard Landlord/Tenant
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Do you have a favorite? Is it ok if your partner does?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?