What is the most interesting question you can ask to get to know someone?
12.06.2025 01:46
49~ How many times have you been married? Why did they end?
42~ What’s your biggest regret in life?
What is your favorite toy? Ever wanted to try a specific toy?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
5~ When you first started having sex, was it what you thought it would be?
I tested Apple’s 11th-gen iPad for a week, and it’s still the best tablet - CNN
82~ Do you have any fantasies involving Role-Playing?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
33- If you could visit any time period, when would you pick? Please explain why?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
36- Do you play video games? What is your favorite? 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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Teacher/Student Stranger/One Night Stand
Nothing too Serious
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
*** Questions about Relationships/Past ***
13- What’s your favorite drink? What’s your least favorite?
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…
8- What are your thoughts on politics?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Knicks' Decision to Fire Tom Thibodeau Was Brewing For 'Months' - Sports Illustrated
76~ Have you had a threesome? Care to Share?
13- What is the craziest/scariest thing you've ever done?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Are you afraid of being alone?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
13- How about having a certain hair cut/style?
22- What is your favorite childhood memory? What is your least favorite?
How to protect yourself from wildfire smoke and poor air quality - The Washington Post
24~ What are your expectations in a relationship? (I know a very big question, take your time)
How about if they talk dirty and/or call you names?
How well do you know me? And some of your thoughts about me
Power Rankings: RBC Canadian Open - PGA Tour
That one or two things that made you go hmmmm, OMG or wow!
92~ Everyone needs a “safe” word. What is yours?
3- What Superhero or Superpower would you want to be/have?
What do you think is the most powerful line in the song "Non, Je Ne Regrette Rien" by Édith Piaf?
What was the longest? What was the shortest?
38~ Share your most embarrassing sexual memory?
12- What’s your favorite food? What’s your least favorite?
What are some creepy bestiality-promoting questions obviously asked for sexual gratification?
15- What bad habit do you wish you could quit? Do you have any addictions?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
51~ What tends to bring a smile to your face?
Would you mind if your partner watched it? How about together vs alone?
How many partners have you had oral sex with? Who? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
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?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
11- How about if they like a certain sports team? 12-How about drinking too much?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
26~ What side of the bed do you sleep on?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
What is your favorite position? Why?
47~ What would be your dream job and why?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
*** Questions About Me ***
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What do you dislike about me? I asked you to be 100% honest.
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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,
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Repairman/Lonely Wife Virgin/Experienced
Would you read them together?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
If you win, what will you make them do?
17- Have you ever done drugs? Which ones? How often?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
18- How often do you drink alcohol? What is your favorite drink?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Would you ever want to be woken up with oral and/or intercourse?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
4- For a pet, Cat, dog or other?
What have you learned about me that was new and/or surprising?
19- What’s your favorite fairytale? What’s your least favorite?
29- How superstitious are you?
Would you do it again, and would you rather 2 females or 2 males?
What is your view on sex? Meaning, When/Where/ How often/
25~ How do you feel about PDA? (Public Display of Affection)
80~ Share your top three fantasies/desires. (Be detailed) 😊
I would allow you to do it… What would you do to me?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Do you have a favorite? Is it ok if your partner does?
9- What’s your favorite season and why? What’s your least favorite?
How many times do you think you have “made love”?
50~ How many children do you have? What are their ages?
2- What’s your favorite color? Do you a least favorite?
*** Random Questions ***
17- What’s your favorite holiday? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
21- What's your favorite way to spend a weekend or time off?
Will you cheat again? How can, you be sure? Define what cheating is to you.
12- What is the weirdest thing you've ever eaten?
13~ Is there a difference between, making love, having sex, and fucking?
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?
Do you watch it? What is your favorite?
Have you ever? Care to Share?
The Ice Breaker Questions
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
83~ How do you feel about Porn?
10~ How many dates are necessary before you to have sex with someone?
9~ How many times over your lifetime do you think you have had sex so far?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
10- What is your favorite family tradition? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a 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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
89~ Do you like taking showers together?
Model/Photographer Police/Criminal
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
34~ Do you like the lights on or off during sex?
Can you Deep Throat? Do you like the taste of yourself?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
Master/Slave Boss/Maid
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
32- What's your greatest talent? Can I see it right now?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Do you think this brought you closer together?
7- What if a person smells a certain way? 8- How about smoking?
52~ Are you willing to make “those types” of bets with your partner?
19- Do/have you smoked? What do you prefer? How often?
31- If given a chance to be immortal, would you take it? Why?
11~ Have you ever been caught by your parents or children or others while having sex?
6- Do you have dreams? Can you remember them? What do you usually dream about?
9- If you could have three wishes, what would they be? Why?
3- Should Pluto still be considered a planet? 4- How about smoking?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
30~ What's something unexpected that turns you on?
(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…)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
53~ How much can you tell me about the one thing you are most passionate about?
51~ Are you willing to play adult games with your partner?
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?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
29~ What are some things that turn you off? What is your biggest turn off?
Family Relation Age Play
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Doctor/Nurse Stripper/Client
62~ Have you used adult toys?
27- What was/ is nickname? Does it have a meaning behind it?
70~ Would/do you have/like anal sex?
How old are you? Male or Female?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
39~ What are your love languages?
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)
81~ Do you have any kinks and/or fetishes?
36~ What is your favorite time of day to have sex/make love?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
23- What is your dream job? What was it as a child?
71~ Would you give your partner a hand or foot job? Would you receive one?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Do you like the “69” position? Do you prefer to be on top or bottom?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
61~ How willing would you be to try new sexual positions?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
You know that I will be 100% truthful, so ask.
5- Have you ever been hypnotized? Would you allow yourself to be?
Do you like it when they show and tell you what they want?
* Give a rating for each one (0-100)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
28- What are some things that people do that irritate you?
1~ How old were you when you had your first kiss? Who? Care to Share?
11- List at least 5 things on your bucket list. Have you done any of them already?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
18~ Who/when was your first “crush”?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Any that are a turn off?
45~ How do you feel about me blindfolding you? How about blindfolding me?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
52~ What are your hobbies?
Nurse/Patient Celebrity/Fan
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Please share Did you stop?
7- What are your thoughts on religion? Is there an afterlife?
48~ Have you ever paid or been paid for sex?
28~ What are some things that turn on? What is your biggest turn on?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Any that are a turn off?
65~ Describe the best orgasm you’ve ever had? Care to share?
3- What’s your favorite smell? Do you a least favorite?
21~ What was the best date you ever went on? What has been the worst?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Escort/Client Job Applicant/Hiring Manager
9- Is there something you’ve always wanted to ask me but you’re afraid?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
14- What's your favorite dessert? Do you a least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
What would you say to prove to yourself that it was really you?
*** Deal Breaker Questions ***
10- List 5 of your top pet peeves.
*** What’s Your Favorite…? ***
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…
If you say it, I will stop, and we can talk about it when you are ready.
41~ Are there moments in your past that you would want to change? Please share 3 of them.
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
1- What was your first impression of me? Has it changed?
67~ Do you like it when your partner moans and/or is vocal during sex?
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?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
14- What is an embarrassing moment in your life? How about your most embarrassing?
44~ Care to share something about yourself that no one else knows about you?
11- What's your favorite restaurant? What’s your least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
37- Do you like your name? If you could change it, what would you change it too?
92~ Have you ever had or have an STD? How many? What was it?
Would /have you ever given your partner a lap dance and Striptease?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
If yes, what?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
19~ Who/when was your first “heartbreak”?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
1- What’s your favorite animal? Do you a least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Over time has your thoughts on sex changed?
Does the thought excite you? Care to share?
What have you learned about yourself that you did not before this?
34- Ever been to a concert? What was your favorite? Who would you like to see?
15- What's your favorite saying? What word or phrase is your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
33- Beach or Mountains? Or is there another place to like better?