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