What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 01:20
Over time has your thoughts on sex changed?
11- How about if they like a certain sports team? 12-How about drinking too much?
17- What’s your favorite holiday? What’s your least favorite?
What is the central theme of the entire Bible in one word (if possible)?
33- Beach or Mountains? Or is there another place to like better?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Get this wrong and this could mean the end… :-) some funny, some not…
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Would you read them together?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
1- What was your first impression of me? Has it changed?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Are you more of a butt guy or a boob guy?
What have you learned about yourself that you did not before this?
10~ How many dates are necessary before you to have sex with someone?
25~ How do you feel about PDA? (Public Display of Affection)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
If you win, what will you make them do?
If Jesus was crucified by Governor Pontius Pilate, why does the Quran deny his death?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
If you lose, are you willing to be their sex slave for a day, (anything goes)?
How about if they talk dirty and/or call you names?
What does it mean when someone is pretending to be me?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
Why do so many people like life?
48~ Have you ever paid or been paid for sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
7-What do I do in bed that drives you wild? How about, what turns you off?
Do Americans realize how much goodwill and credibility they've lost in the past two weeks?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
Do you think this brought you closer together?
Jonas Brothers cancel and move upcoming concerts, including one in North Texas - WFAA
1~ How old were you when you had your first kiss? Who? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Nothing too Serious
What was your most embarrassing wardrobe malfunction in public?
Can you Deep Throat? Do you like the taste of yourself?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
When gallery photos are deleted at the same time, why are Google photos also deleted?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
26~ What side of the bed do you sleep on?
Does the thought excite you? Care to share?
How conservative the Japanese people really is? And the government?
38~ Share your most embarrassing sexual memory?
Would /have you ever given your partner a lap dance and Striptease?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you respect the US with a woman as president?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
How many partners have you had oral sex with? Who? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Would you mind if your partner watched it? How about together vs alone?
44~ Care to share something about yourself that no one else knows about you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
30~ What's something unexpected that turns you on?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
13- What’s your favorite drink? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
76~ Have you had a threesome? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
37- Do you like your name? If you could change it, what would you change it too?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
52~ Are you willing to make “those types” of bets with your partner?
40~ What’s the weirdest place you’ve ever had sex?
11- List at least 5 things on your bucket list. Have you done any of them already?
92~ Have you ever had or have an STD? How many? What was it?
18~ Who/when was your first “crush”?
32- What's your greatest talent? Can I see it right now?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
62~ Have you used adult toys?
If yes, what?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
I would allow you to do it… What would you do to me?
18- How often do you drink alcohol? What is your favorite drink?
42~ What’s your biggest regret in life?
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?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
9- Is there something you’ve always wanted to ask me but you’re afraid?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Doctor/Nurse Stripper/Client
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
8- What's your favorite flavor of ice cream? Do you a least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
How many times do you think you have “made love”?
52~ What are your hobbies?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
You know that I will be 100% truthful, so ask.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
89~ Do you like taking showers together?
Model/Photographer Police/Criminal
15~ Have you ever been “in love”? Who? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Any that are a turn off?
(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…)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Would you do it again, and would you rather 2 females or 2 males?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What would you say to prove to yourself that it was really you?
4- For a pet, Cat, dog or other?
19- Do/have you smoked? What do you prefer? How often?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
5~ When you first started having sex, was it what you thought it would be?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
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?
7- What if a person smells a certain way? 8- How about smoking?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Any that are a turn off?
3- What Superhero or Superpower would you want to be/have?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
What is your favorite position? Why?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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…
19- What’s your favorite fairytale? What’s your least favorite?
*** Deal Breaker Questions ***
Nurse/Patient Celebrity/Fan
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
*** Questions about Relationships/Past ***
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
29~ What are some things that turn you off? What is your biggest turn off?
9~ How many times over your lifetime do you think you have had sex so far?
Do you watch it? What is your favorite?
51~ What tends to bring a smile to your face?
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?
36~ What is your favorite time of day to have sex/make love?
What do you dislike about me? I asked you to be 100% honest.
15- What's your favorite saying? What word or phrase is your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
67~ Do you like it when your partner moans and/or is vocal during sex?
10- List 5 of your top pet peeves.
Prisoner/Prison Guard Landlord/Tenant
41~ Are there moments in your past that you would want to change? Please share 3 of them.
84~ How do you feel about reading/listening to adult stories?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
45~ How do you feel about me blindfolding you? How about blindfolding me?
11- What's your favorite restaurant? What’s your least favorite?
13- What is the craziest/scariest thing you've ever done?
13- How about having a certain hair cut/style?
65~ Describe the best orgasm you’ve ever had? Care to share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
14- What is an embarrassing moment in your life? How about your most embarrassing?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
49~ How many times have you been married? Why did they end?
Have you ever? Care to Share?
21- What's your favorite way to spend a weekend or time off?
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 old are you? Male or Female?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
61~ How willing would you be to try new sexual positions?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
9- What’s your favorite season and why? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
23- What is your dream job? What was it as a child?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Will you cheat again? How can, you be sure? Define what cheating is to you.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
5- Have you ever been hypnotized? Would you allow yourself to be?
20- What’s your favorite candy? What’s your least favorite?
81~ Do you have any kinks and/or fetishes?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
29- How superstitious are you?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Repairman/Lonely Wife Virgin/Experienced
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
34~ Do you like the lights on or off during sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What have you learned about me that was new and/or surprising?
2- What’s your favorite color? Do you a least favorite?
28~ What are some things that turn on? What is your biggest turn on?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you have a favorite? Is it ok if your partner does?
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…
49~ If you could, would you want to be the opposite sex for a day, week, or year?
92~ Everyone needs a “safe” word. What is yours?
71~ Would you give your partner a hand or foot job? Would you receive one?
11~ Have you ever been caught by your parents or children or others while having sex?
*** Random Questions ***
22- What is your favorite childhood memory? What is your least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
70~ Would/do you have/like anal sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
13~ Is there a difference between, making love, having sex, and fucking?
Do you like it when they show and tell you what they want?
How well do you know me? And some of your thoughts about me
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
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?
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?
39~ What are your love languages?
What is your view on sex? Meaning, When/Where/ How often/
17- Have you ever done drugs? Which ones? How often?
What was the longest? What was the shortest?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
* Give a rating for each one (0-100)
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
3- What’s your favorite smell? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
50~ How many children do you have? What are their ages?
48~ Do you have any siblings? Are you close to your family?
19~ Who/when was your first “heartbreak”?
33- If you could visit any time period, when would you pick? Please explain why?
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?
*** Questions About Me ***
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
10- What is your favorite family tradition? What’s your least favorite?
Escort/Client Job Applicant/Hiring Manager
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
8- What are your thoughts on politics?
12- What’s your favorite food? What’s your least favorite?
9- If you could have three wishes, what would they be? Why?
83~ How do you feel about Porn?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
*** What’s Your Favorite…? ***
31- If given a chance to be immortal, would you take it? Why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
If you say it, I will stop, and we can talk about it when you are ready.
Family Relation Age Play
14- What's your favorite dessert? Do you a least favorite?
12- What is the weirdest thing you've ever eaten?
Please share Did you stop?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Master/Slave Boss/Maid
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would you allow me to clean every part of your body with my soapy hands and fingers?
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,
The Ice Breaker Questions
35- Do you like playing board or cards game? 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?
47~ What would be your dream job and why?
51~ Are you willing to play adult games with your partner?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
15- What bad habit do you wish you could quit? Do you have any addictions?