What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 02:28
60~ How important is oral sex? Do you like receiving? Do you like giving?
49~ How many times have you been married? Why did they end?
36- Do you play video games? What is your favorite? Do you a least favorite?
92~ Everyone needs a “safe” word. What is yours?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Have you ever? Care to Share?
Why do men think I’m easy just by looking at me?
20- What’s your favorite candy? What’s your least favorite?
The Ice Breaker Questions
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What’s the best way to get over someone you love?
Would /have you ever given your partner a lap dance and Striptease?
1~ How old were you when you had your first kiss? Who? Care to Share?
34~ Do you like the lights on or off during sex?
What happens when you get sick in a country with universal healthcare? What's the process like?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
42~ What’s your biggest regret in life?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
That one or two things that made you go hmmmm, OMG or wow!
80~ Share your top three fantasies/desires. (Be detailed) 😊
Can you Deep Throat? Do you like the taste of yourself?
What can you do if someone makes a false accusation against you?
What would you say to prove to yourself that it was really you?
Do you like it when they show and tell you what they want?
9- What’s your favorite season and why? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
44~ Care to share something about yourself that no one else knows about you?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
What happened to The Simpsons deleted onscreen footage?
52~ What are your hobbies?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
19- What’s your favorite fairytale? What’s your least favorite?
How well do you know me? And some of your thoughts about me
What is your view on sex? Meaning, When/Where/ How often/
45~ How do you feel about me blindfolding you? How about blindfolding me?
How do you fight the push and pull (manipulation) tactic if you want to win him?
If you say it, I will stop, and we can talk about it when you are ready.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
22- What is your favorite childhood memory? What is your least favorite?
Is it right to visit any shrine or tomb in Islam?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
9~ How many times over your lifetime do you think you have had sex so far?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Can a Trump supporter explain what was wrong with what Bishop Budde said to Donald Trump?
I would allow you to do it… What would you do to me?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
76~ Have you had a threesome? Care to Share?
What do women talk about mostly(among themselves)?
26~ What side of the bed do you sleep on?
15- What bad habit do you wish you could quit? Do you have any addictions?
65~ Describe the best orgasm you’ve ever had? Care to share?
What are some photos of masturbation?
36~ What is your favorite time of day to have sex/make love?
51~ What tends to bring a smile to your face?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Why is the word "democracy" not in the preamble of the US Constitution?
38~ Share your most embarrassing sexual memory?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Get this wrong and this could mean the end… :-) some funny, some not…
19- Do/have you smoked? What do you prefer? How often?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
31- If given a chance to be immortal, would you take it? Why?
Family Relation Age Play
*** Questions About Me ***
32- What's your greatest talent? Can I see it right now?
19~ Who/when was your first “heartbreak”?
11- How about if they like a certain sports team? 12-How about drinking too much?
How old are you? Male or Female?
Repairman/Lonely Wife Virgin/Experienced
13~ Is there a difference between, making love, having sex, and fucking?
Any that are a turn off?
Would you read them together?
*** Deal Breaker Questions ***
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
*** Random Questions ***
If you win, what will you make them do?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
28- What are some things that people do that irritate you?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
84~ How do you feel about reading/listening to adult stories?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
83~ How do you feel about Porn?
3- What’s your favorite smell? Do you a least favorite?
92~ Have you ever had or have an STD? How many? What was it?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
5- Have you ever been hypnotized? Would you allow yourself to be?
12- What’s your favorite food? What’s your least favorite?
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,
70~ Would/do you have/like anal sex?
7- What are your thoughts on religion? Is there an afterlife?
10- What is your favorite family tradition? What’s your least favorite?
What do you dislike about me? I asked you to be 100% honest.
What is your favorite position? Why?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
33- If you could visit any time period, when would you pick? Please explain why?
* Give a rating for each one (0-100)
How about if they talk dirty and/or call you names?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
9- Is there something you’ve always wanted to ask me but you’re afraid?
13- How about having a certain hair cut/style?
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?
51~ Are you willing to play adult games with your partner?
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…
Please share Did you stop?
Will you cheat again? How can, you be sure? Define what cheating is to you.
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
21~ What was the best date you ever went on? What has been the worst?
28~ What are some things that turn on? What is your biggest turn on?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
15~ Have you ever been “in love”? Who? 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?
14- What's your favorite dessert? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
Nurse/Patient Celebrity/Fan
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Prisoner/Prison Guard Landlord/Tenant
13- What is the craziest/scariest thing you've ever done?
81~ Do you have any kinks and/or fetishes?
89~ Do you like taking showers together?
53~ How much can you tell me about the one thing you are most passionate about?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
71~ Would you give your partner a hand or foot job? Would you receive one?
Do you think this brought you closer together?
39~ What are your love languages?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Does the thought excite you? Care to share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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~ What would be your dream job and why?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
1- What was your first impression of me? Has it changed?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
(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…)
40~ What’s the weirdest place you’ve ever had sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
18- What’s your favorite way to relax after a long day? What’s your 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?
7-What do I do in bed that drives you wild? How about, what turns you off?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
25~ How do you feel about PDA? (Public Display of Affection)
Model/Photographer Police/Criminal
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)
12- What is the weirdest thing you've ever eaten?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Nothing too Serious
5~ When you first started having sex, was it what you thought it would be?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What have you learned about yourself that you did not before this?
You know that I will be 100% truthful, so ask.
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?
1- What’s your favorite animal? Do you a least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
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?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
50~ How many children do you have? What are their ages?
*** What’s Your Favorite…? ***
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
10- List 5 of your top pet peeves.
How many partners have you had oral sex with? Who? Care to Share?
Do you watch it? What is your favorite?
37- Do you like your name? If you could change it, what would you change it too?
67~ Do you like it when your partner moans and/or is vocal during sex?
13- What’s your favorite drink? What’s your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
11~ Have you ever been caught by your parents or children or others while having sex?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
11- List at least 5 things on your bucket list. Have you done any of them already?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
6- Do you have dreams? Can you remember them? What do you usually dream about?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
14- What is an embarrassing moment in your life? How about your most embarrassing?
How many times do you think you have “made love”?
10~ How many dates are necessary before you to have sex with someone?
17- Have you ever done drugs? Which ones? How often?
52~ Are you willing to make “those types” of bets with your partner?
If yes, what?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
29- How superstitious are you?
17- What’s your favorite holiday? What’s your least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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…
What is your favorite toy? Ever wanted to try a specific toy?
3- What Superhero or Superpower would you want to be/have?
15- What's your favorite saying? What word or phrase is your least favorite?
Any that are a turn off?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
33- Beach or Mountains? Or is there another place to like better?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
What have you learned about me that was new and/or surprising?
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?
4- For a pet, Cat, dog or other?
2- What’s your favorite color? Do you a least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you have a favorite? Is it ok if your partner does?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
7- What if a person smells a certain way? 8- How about smoking?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
62~ Have you used adult toys?
29~ What are some things that turn you off? What is your biggest turn off?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Master/Slave Boss/Maid
Doctor/Nurse Stripper/Client
*** Questions about Relationships/Past ***
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
21- What's your favorite way to spend a weekend or time off?
30~ What's something unexpected that turns you on?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Teacher/Student Stranger/One Night Stand
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Escort/Client Job Applicant/Hiring Manager
If NO, would you ever have one? Would it be with 2 men or 2 women?
8- What are your thoughts on politics?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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 clean every part of your body with my soapy hands and fingers?
61~ How willing would you be to try new sexual positions?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
What was the longest? What was the shortest?
23- What is your dream job? What was it as a child?
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?
9- If you could have three wishes, what would they be? Why?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Would you ever want to be woken up with oral and/or intercourse?
27- What was/ is nickname? Does it have a meaning behind it?
Over time has your thoughts on sex changed?
Would you mind if your partner watched it? How about together vs alone?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
18- How often do you drink alcohol? What is your favorite drink?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
48~ Do you have any siblings? Are you close to your family?
82~ Do you have any fantasies involving Role-Playing?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
18~ Who/when was your first “crush”?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.