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