What is the most interesting question you can ask to get to know someone?
Last Updated: 16.06.2025 13:04
Do you think this brought you closer together?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
12- What’s your favorite food? What’s your least favorite?
What is the most memorable thing that happened in your college days?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
47~ What would be your dream job and why?
That one or two things that made you go hmmmm, OMG or wow!
What happens psychologically to a man the first time he gets penetrated anally?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Nurse/Patient Celebrity/Fan
How do you help patients stop hearing voices?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
3- Should Pluto still be considered a planet? 4- How about smoking?
What are the pros and cons of living in Male, Maldives?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
30~ What's something unexpected that turns you on?
Does the thought excite you? Care to share?
Why did my ex move on so quickly?
65~ Describe the best orgasm you’ve ever had? Care to share?
Would /have you ever given your partner a lap dance and Striptease?
3- What Superhero or Superpower would you want to be/have?
Why after 50 years of being straight do I constantly desire to suck cock?
61~ How willing would you be to try new sexual positions?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Would you read them together?
13- What is the craziest/scariest thing you've ever done?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
83~ How do you feel about Porn?
Do you find Anushka Sen attractive?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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?
18- How often do you drink alcohol? What is your favorite drink?
What is the most inappropriate experience you have had with a friend's daughter?
10~ How many dates are necessary before you to have sex with someone?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
2- What’s your favorite color? Do you a least favorite?
Does the Hamas charter specifically call for the death of all Jews and the destruction of Israel?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? 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?
27- What was/ is nickname? Does it have a meaning behind it?
Have you experimented with bestiality?
What was the longest? What was the shortest?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
21- What's your favorite way to spend a weekend or time off?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
4- For a pet, Cat, dog or other?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
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?
Model/Photographer Police/Criminal
34- Ever been to a concert? What was your favorite? Who would you like to see?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
7- What are your thoughts on religion? Is there an afterlife?
1- What’s your favorite animal? Do you a least favorite?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
9- If you could have three wishes, what would they be? 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…
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
I would allow you to do it… What would you do to me?
82~ Do you have any fantasies involving Role-Playing?
What do you dislike about me? I asked you to be 100% honest.
26~ What side of the bed do you sleep on?
You know that I will be 100% truthful, so ask.
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Please share Did you stop?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Doctor/Nurse Stripper/Client
1- What was your first impression of me? Has it changed?
If yes, what?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
33- Beach or Mountains? Or is there another place to like better?
92~ Have you ever had or have an STD? How many? What was it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
How well do you know me? And some of your thoughts about me
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Escort/Client Job Applicant/Hiring Manager
The Ice Breaker Questions
34~ Do you like the lights on or off during sex?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Nothing too Serious
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
7- What if a person smells a certain way? 8- How about smoking?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Repairman/Lonely Wife Virgin/Experienced
89~ Do you like taking showers together?
*** Questions About Me ***
8- What's your favorite flavor of ice cream? Do you a least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How many partners have you had oral sex with? Who? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
40~ What’s the weirdest place you’ve ever had sex?
38~ Share your most embarrassing sexual memory?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Any that are a turn off?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
How many times do you think you have “made love”?
22- What is your favorite childhood memory? What is your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
15- What's your favorite saying? What word or phrase is your least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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,
Do you have a favorite? Is it ok if your partner does?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
*** Questions about Relationships/Past ***
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What have you learned about yourself that you did not before this?
What is your favorite position? Why?
36~ What is your favorite time of day to have sex/make love?
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?
51~ Are you willing to play adult games with your partner?
49~ How many times have you been married? Why did they end?
19- What’s your favorite fairytale? What’s your least favorite?
Would you mind if your partner watched it? How about together vs alone?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
11- How about if they like a certain sports team? 12-How about drinking too much?
37- Do you like your name? If you could change it, what would you change it too?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Do you watch it? What is your favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
9- Is there something you’ve always wanted to ask me but you’re afraid?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
14- What is an embarrassing moment in your life? How about your most embarrassing?
17- What’s your favorite holiday? What’s your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
How old are you? Male or Female?
Get this wrong and this could mean the end… :-) some funny, some not…
13~ Is there a difference between, making love, having sex, and fucking?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
11- What's your favorite restaurant? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
1~ How old were you when you had your first kiss? Who? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
18- What’s your favorite way to relax after a long day? What’s your least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
67~ Do you like it when your partner moans and/or is vocal during sex?
*** Deal Breaker Questions ***
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
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 do it again, and would you rather 2 females or 2 males?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
36- Do you play video games? What is your favorite? Do you a least favorite?
19- Do/have you smoked? What do you prefer? How often?
9- What’s your favorite season and why? What’s your least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
51~ What tends to bring a smile to your face?
*** Random Questions ***
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
5~ When you first started having sex, was it what you thought it would be?
15- What bad habit do you wish you could quit? Do you have any addictions?
42~ What’s your biggest regret in life?
Have you ever? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
10- What is your favorite family tradition? What’s your least favorite?
*** What’s Your Favorite…? ***
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
If NO, would you ever have one? Would it be with 2 men or 2 women?
70~ Would/do you have/like anal sex?
How about if they talk dirty and/or call you names?
What is your view on sex? Meaning, When/Where/ How often/
19~ Who/when was your first “heartbreak”?
13- How about having a certain hair cut/style?
Would you ever want to be woken up with oral and/or intercourse?
44~ Care to share something about yourself that no one else knows about you?
21~ What was the best date you ever went on? What has been the worst?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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?
60~ How important is oral sex? Do you like receiving? Do you like giving?
48~ Do you have any siblings? Are you close to your family?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
14- What's your favorite dessert? Do you a least favorite?
52~ What are your hobbies?
81~ Do you have any kinks and/or fetishes?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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?
76~ Have you had a threesome? Care to Share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
10- List 5 of your top pet peeves.
What have you learned about me that was new and/or surprising?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Over time has your thoughts on sex changed?
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…
48~ Have you ever paid or been paid for sex?
31- If given a chance to be immortal, would you take it? Why?
Master/Slave Boss/Maid
What’s the longest time you gone without having sex, after, having it? How much time between the others?
(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…)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
What would you say to prove to yourself that it was really you?
50~ How many children do you have? What are their ages?
32- What's your greatest talent? Can I see it right now?
45~ How do you feel about me blindfolding you? How about blindfolding me?
62~ Have you used adult toys?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Do you like it when they show and tell you what they want?
Can you Deep Throat? Do you like the taste of yourself?
Teacher/Student Stranger/One Night Stand
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
18~ Who/when was your first “crush”?
11- List at least 5 things on your bucket list. Have you done any of them already?
12- What is the weirdest thing you've ever eaten?
Prisoner/Prison Guard Landlord/Tenant
3- What’s your favorite smell? Do you a least favorite?
Family Relation Age Play
Any that are a turn off?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
29- How superstitious are you?
39~ What are your love languages?
11~ Have you ever been caught by your parents or children or others while having sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
* Give a rating for each one (0-100)
53~ How much can you tell me about the one thing you are most passionate about?
28- What are some things that people do that irritate you?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
23- What is your dream job? What was it as a child?
17- Have you ever done drugs? Which ones? How often?
52~ Are you willing to make “those types” of bets with your partner?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
If you win, what will you make them do?
33- If you could visit any time period, when would you pick? Please explain why?
What is your favorite toy? Ever wanted to try a specific toy?
29~ What are some things that turn you off? What is your biggest turn off?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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)
7-What do I do in bed that drives you wild? How about, what turns you off?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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?
8- What are your thoughts on politics?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
9~ How many times over your lifetime do you think you have had sex so far?