What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 02:43
10- List 5 of your top pet peeves.
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Why do some men like anal sex?
7- What are your thoughts on religion? Is there an afterlife?
Family Relation Age Play
44~ Care to share something about yourself that no one else knows about you?
Have you ever seen your wife being fucked?
The Ice Breaker Questions
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
What are some ballbusting stories?
29~ What are some things that turn you off? What is your biggest turn off?
13~ Is there a difference between, making love, having sex, and fucking?
10- What is your favorite family tradition? What’s your least favorite?
Is it because Trump is impulsive that he is never on time?
31- If given a chance to be immortal, would you take it? Why?
28~ What are some things that turn on? What is your biggest turn on?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
*** Questions About Me ***
Model/Photographer Police/Criminal
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
How do you fight the push and pull (manipulation) tactic if you want to win him?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What is your favorite toy? Ever wanted to try a specific toy?
40~ What’s the weirdest place you’ve ever had sex?
Why is social media so anti-fee speech, and have they become total BS?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Get this wrong and this could mean the end… :-) some funny, some not…
7- What if a person smells a certain way? 8- How about smoking?
How often do prisoners try to escape from jail/prison, and how many of them succeed?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
How old are you? Male or Female?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What is your view on sex? Meaning, When/Where/ How often/
80~ Share your top three fantasies/desires. (Be detailed) 😊
What 10 things have you stopped doing in your life?
Please share Did you stop?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
9- What’s your favorite season and why? What’s your least favorite?
How do you know how physically attractive you actually are?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you watch it? What is your favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Older Americans are happiest living in these 5 US states, study says — is yours one of them? - Yahoo
2- What’s your favorite color? Do you a least favorite?
Over time has your thoughts on sex changed?
17- Have you ever done drugs? Which ones? How often?
Master/Slave Boss/Maid
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Have you ever? Care to Share?
83~ How do you feel about Porn?
If NO, would you ever have one? Would it be with 2 men or 2 women?
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- Do you have dreams? Can you remember them? What do you usually dream about?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
9~ How many times over your lifetime do you think you have had sex so far?
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
67~ Do you like it when your partner moans and/or is vocal during sex?
Prisoner/Prison Guard Landlord/Tenant
* 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?
17- What’s your favorite holiday? What’s your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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…
*** Random Questions ***
3- What was the most surprising thing you’ve learned about me throughout our relationship?
13- What’s your favorite drink? What’s your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
You know that I will be 100% truthful, so ask.
30~ What's something unexpected that turns you on?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you think this brought you closer together?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
61~ How willing would you be to try new sexual positions?
Does the thought excite you? Care to share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
48~ Do you have any siblings? Are you close to your family?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Escort/Client Job Applicant/Hiring Manager
*** What’s Your Favorite…? ***
42~ What’s your biggest regret in life?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
1- What’s your favorite animal? Do you a least favorite?
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?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
Would /have you ever given your partner a lap dance and Striptease?
19- What’s your favorite fairytale? What’s your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
15~ Have you ever been “in love”? Who? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
48~ Have you ever paid or been paid for sex?
36~ What is your favorite time of day to have sex/make love?
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?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** Questions about Relationships/Past ***
If you win, what will you make them do?
28- What are some things that people do that irritate you?
26~ What side of the bed do you sleep on?
9- If you could have three wishes, what would they be? Why?
Nothing too Serious
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
47~ What would be your dream job and why?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
52~ What are your hobbies?
Would you ever want to be woken up with oral and/or intercourse?
51~ What tends to bring a smile to your face?
14- What's your favorite dessert? Do you a least favorite?
Any that are a turn off?
53~ How much can you tell me about the one thing you are most passionate about?
What have you learned about me that was new and/or surprising?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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?
That one or two things that made you go hmmmm, OMG or wow!
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
89~ Do you like taking showers together?
21~ What was the best date you ever went on? What has been the worst?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
11- What's your favorite restaurant? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
13- How about having a certain hair cut/style?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
19- Do/have you smoked? What do you prefer? How often?
Would you do it again, and would you rather 2 females or 2 males?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
36- Do you play video games? What is your favorite? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
11- List at least 5 things on your bucket list. Have you done any of them already?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
32- What's your greatest talent? Can I see it right now?
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?
How about if they talk dirty and/or call you names?
3- What’s your favorite smell? Do you a least favorite?
4- For a pet, Cat, dog or other?
How many partners have you had oral sex with? Who? Care to Share?
What was the longest? What was the shortest?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Doctor/Nurse Stripper/Client
52~ Are you willing to make “those types” of bets with your partner?
If YES, was it with 2 men or 2 women? Did you enjoy it?
18- How often do you drink alcohol? What is your favorite drink?
I would allow you to do it… What would you do to me?
76~ Have you had a threesome? Care to Share?
81~ Do you have any kinks and/or fetishes?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
29- How superstitious are you?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Any that are a turn off?
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,
38~ Share your most embarrassing sexual memory?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
What do you dislike about me? I asked you to be 100% honest.
51~ Are you willing to play adult games with your partner?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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)
13- What is the craziest/scariest thing you've ever done?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
18~ Who/when was your first “crush”?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
1~ How old were you when you had your first kiss? Who? Care to Share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
84~ How do you feel about reading/listening to adult stories?
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…
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
39~ What are your love languages?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
49~ How many times have you been married? Why did they end?
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Would you read them together?
5- Have you ever been hypnotized? Would you allow yourself to be?
27- What was/ is nickname? Does it have a meaning behind it?
If yes, what?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Teacher/Student Stranger/One Night Stand
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
23- What is your dream job? What was it as a child?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
How many times do you think you have “made love”?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What is your favorite position? Why?
15- What's your favorite saying? What word or phrase is your least favorite?
*** Deal Breaker Questions ***
92~ Have you ever had or have an STD? How many? What was it?
20- What’s your favorite candy? What’s your least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
62~ Have you used adult toys?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
11- How about if they like a certain sports team? 12-How about drinking too much?
15- What bad habit do you wish you could quit? Do you have any addictions?
3- What Superhero or Superpower would you want to be/have?
10~ How many dates are necessary before you to have sex with someone?
Would you mind if your partner watched it? How about together vs alone?
33- Beach or Mountains? Or is there another place to like better?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How well do you know me? And some of your thoughts about me
82~ Do you have any fantasies involving Role-Playing?
(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…)
50~ How many children do you have? What are their ages?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
22- What is your favorite childhood memory? What is your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
37- Do you like your name? If you could change it, what would you change it too?
Nurse/Patient Celebrity/Fan
22- Do you have any birth marks? How about scars? Care to share how you got them?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
34~ Do you like the lights on or off during sex?
11~ Have you ever been caught by your parents or children or others while having sex?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
What would you say to prove to yourself that it was really you?
21- What's your favorite way to spend a weekend or time off?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
12- What’s your favorite food? What’s your least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
7-What do I do in bed that drives you wild? How about, what turns you off?
3- Should Pluto still be considered a planet? 4- How about smoking?
5~ When you first started having sex, was it what you thought it would be?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
33- If you could visit any time period, when would you pick? Please explain why?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Do you like it when they show and tell you what they want?
34- Ever been to a concert? What was your favorite? Who would you like to see?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
1- What was your first impression of me? Has it changed?
8- What are your thoughts on politics?
Will you cheat again? How can, you be sure? Define what cheating is to you.
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
60~ How important is oral sex? Do you like receiving? Do you like giving?
8- What's your favorite flavor of ice cream? Do you a least favorite?
12- What is the weirdest thing you've ever eaten?
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?
What have you learned about yourself that you did not before this?
19~ Who/when was your first “heartbreak”?
70~ Would/do you have/like anal sex?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Repairman/Lonely Wife Virgin/Experienced
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?