What is the most interesting question you can ask to get to know someone?
09.06.2025 01:33
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…
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Do you watch it? What is your favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Circle IPO Is Said to Price Above Range to Raise $1.1 Billion - Bloomberg
36- Do you play video games? What is your favorite? Do you a least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Bethenny Frankel Reveals Her Teenage Daughter Bryn's Reaction to Her SI Swimsuit Look - People.com
If you say it, I will stop, and we can talk about it when you are ready.
What would you say to prove to yourself that it was really you?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
Family Relation Age Play
30~ What's something unexpected that turns you on?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
47~ What would be your dream job and why?
Subway owner buys popular chicken chain in $1 billion deal - PennLive.com
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?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
33- Beach or Mountains? Or is there another place to like better?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
33- If you could visit any time period, when would you pick? Please explain why?
Senators get ready to roll out a new crypto bill - Politico
51~ Are you willing to play adult games with your partner?
What is your favorite position? Why?
If yes, what?
44~ Care to share something about yourself that no one else knows about you?
5~ When you first started having sex, was it what you thought it would be?
31- If given a chance to be immortal, would you take it? Why?
Who is Meghan Markle and why is she so controversial on the Internet?
50~ How many children do you have? What are their ages?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
53~ How much can you tell me about the one thing you are most passionate about?
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80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
12- What is the weirdest thing you've ever eaten?
Can supporters of gun control explain the purpose behind a gun registry?
3- What Superhero or Superpower would you want to be/have?
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
What is the correct way to say "my pleasure" in French in the context of having given a gift?
62~ Have you used adult toys?
Would you allow me to clean every part of your body with my soapy hands and fingers?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Are evolutionists giving evolution a bad name by claiming humans started off as shrews?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Please share Did you stop?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
* Give a rating for each one (0-100)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
23- What is your dream job? What was it as a child?
39~ What are your love languages?
19- Do/have you smoked? What do you prefer? How often?
8- What are your thoughts on politics?
36~ What is your favorite time of day to have sex/make love?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
17- Have you ever done drugs? Which ones? How often?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
What do you dislike about me? I asked you to be 100% honest.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
7- What if a person smells a certain way? 8- How about smoking?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
11- List at least 5 things on your bucket list. Have you done any of them already?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
8- What's your favorite flavor of ice cream? Do you a least favorite?
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?
17- What’s your favorite holiday? What’s your least favorite?
34~ Do you like the lights on or off during sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
1~ How old were you when you had your first kiss? Who? Care to Share?
Master/Slave Boss/Maid
11~ Have you ever been caught by your parents or children or others while having sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
20- What’s your favorite candy? What’s your least favorite?
28- What are some things that people do that irritate you?
How well do you know me? And some of your thoughts about me
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
10- List 5 of your top pet peeves.
Would you read them together?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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?
What is your view on sex? Meaning, When/Where/ How often/
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,
Would you mind if your partner watched it? How about together vs alone?
28~ What are some things that turn on? What is your biggest turn on?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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…
13- What is the craziest/scariest thing you've ever done?
How about if they talk dirty and/or call you names?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
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)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
3- What’s your favorite smell? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
How many times do you think you have “made love”?
Repairman/Lonely Wife Virgin/Experienced
34- Ever been to a concert? What was your favorite? Who would you like to see?
*** Questions about Relationships/Past ***
18- How often do you drink alcohol? What is your favorite drink?
81~ Do you have any kinks and/or fetishes?
48~ Have you ever paid or been paid for sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
How old are you? Male or Female?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Model/Photographer Police/Criminal
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
*** What’s Your Favorite…? ***
5- Have you ever been hypnotized? Would you allow yourself to be?
29- How superstitious are you?
Doctor/Nurse Stripper/Client
27- What was/ is nickname? Does it have a meaning behind it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Over time has your thoughts on sex changed?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Get this wrong and this could mean the end… :-) some funny, some not…
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
18~ Who/when was your first “crush”?
13- What’s your favorite drink? What’s your least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Prisoner/Prison Guard Landlord/Tenant
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
40~ What’s the weirdest place you’ve ever had sex?
38~ Share your most embarrassing sexual memory?
76~ Have you had a threesome? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
83~ How do you feel about Porn?
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?
What have you learned about me that was new and/or surprising?
What is your favorite toy? Ever wanted to try a specific toy?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
13- How about having a certain hair cut/style?
25~ How do you feel about PDA? (Public Display of Affection)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
7- What are your thoughts on religion? Is there an afterlife?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
4- For a pet, Cat, dog or other?
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?
21~ What was the best date you ever went on? What has been the worst?
26~ What side of the bed do you sleep on?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
89~ Do you like taking showers together?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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?
11- What's your favorite restaurant? What’s your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
37- Do you like your name? If you could change it, what would you change it too?
9- If you could have three wishes, what would they be? Why?
What was the longest? What was the shortest?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
9~ How many times over your lifetime do you think you have had sex so far?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
67~ Do you like it when your partner moans and/or is vocal during sex?
61~ How willing would you be to try new sexual positions?
If NO, would you ever have one? Would it be with 2 men or 2 women?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you have a favorite? Is it ok if your partner does?
*** Deal Breaker Questions ***
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
10~ How many dates are necessary before you to have sex with someone?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
70~ Would/do you have/like anal sex?
I would allow you to do it… What would you do to me?
Would you ever want to be woken up with oral and/or intercourse?
How many partners have you had oral sex with? Who? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Do you think this brought you closer together?
19~ Who/when was your first “heartbreak”?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
(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…)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Do you like it when they show and tell you what they want?
49~ How many times have you been married? Why did they end?
65~ Describe the best orgasm you’ve ever had? Care to share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
51~ What tends to bring a smile to your face?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
2- What’s your favorite color? Do you a least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
You know that I will be 100% truthful, so ask.
Do you like the “69” position? Do you prefer to be on top or bottom?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Does the thought excite you? Care to share?
Escort/Client Job Applicant/Hiring Manager
3- Should Pluto still be considered a planet? 4- How about smoking?
19- What’s your favorite fairytale? What’s your least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
*** Questions About Me ***
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
3- What was the most surprising thing you’ve learned about me throughout our relationship?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
If you win, what will you make them do?
Can you Deep Throat? Do you like the taste of yourself?
11- How about if they like a certain sports team? 12-How about drinking too much?
9- What’s your favorite season and why? What’s your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Any that are a turn off?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
10- What is your favorite family tradition? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
Have you ever? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
52~ Are you willing to make “those types” of bets with your partner?
1- What’s your favorite animal? 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?
42~ What’s your biggest regret in life?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Nothing too Serious
22- What is your favorite childhood memory? What is your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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?
*** Random Questions ***
22~ What is the best pickup line anyone has ever used on you? What was the worst?
12- What’s your favorite food? What’s your least favorite?
What have you learned about yourself that you did not before this?
60~ How important is oral sex? Do you like receiving? Do you like giving?
48~ Do you have any siblings? Are you close to your family?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
82~ Do you have any fantasies involving Role-Playing?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Teacher/Student Stranger/One Night Stand
Would /have you ever given your partner a lap dance and Striptease?
1- What was your first impression of me? Has it changed?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
The Ice Breaker Questions
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
13~ Is there a difference between, making love, having sex, and fucking?
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!
Would you do it again, and would you rather 2 females or 2 males?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Nurse/Patient Celebrity/Fan
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
52~ What are your hobbies?
92~ Have you ever had or have an STD? How many? What was it?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
15~ Have you ever been “in love”? Who? Care to Share?
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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?