What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 00:11
Any that are a turn off?
33- Beach or Mountains? Or is there another place to like better?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Why do companies cull employees during financial downturns without saying so?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What was the longest? What was the shortest?
11- What's your favorite restaurant? What’s your least favorite?
Why is Donald Trump criticized by so many people?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
28~ What are some things that turn on? What is your biggest turn on?
18- How often do you drink alcohol? What is your favorite drink?
Cher’s son Elijah Blue Allman hospitalized after drug overdose: report - Page Six
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?
67~ Do you like it when your partner moans and/or is vocal during sex?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What does it feel like to "lose your looks" to age?
What is your view on sex? Meaning, When/Where/ How often/
Any that are a turn off?
I would allow you to do it… What would you do to me?
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…
5~ When you first started having sex, was it what you thought it would be?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
21~ What was the best date you ever went on? What has been the worst?
44~ Care to share something about yourself that no one else knows about you?
Why didn't Taylor Swift do Taylor Swift (Taylors version)?
What would you say to prove to yourself that it was really you?
26~ What side of the bed do you sleep on?
70~ Would/do you have/like anal sex?
Which is a better option, a love marriage or an arranged marriage in India?
3- What’s your favorite smell? Do you a least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What is your favorite underrated movie and why? What makes it underrated? How did you find it?
9- If you could have three wishes, what would they be? Why?
60~ How important is oral sex? Do you like receiving? Do you like giving?
What have you learned about me that was new and/or surprising?
Red Dead Redemption's John Marston Actor Teases "Exciting News" Coming Soon - GameSpot
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
10- What is your favorite family tradition? What’s your least favorite?
Nothing too Serious
34~ Do you like the lights on or off during sex?
*** Questions about Relationships/Past ***
*** Deal Breaker Questions ***
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Please share Did you stop?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
38~ Share your most embarrassing sexual memory?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
23- What is your dream job? What was it as a child?
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?
2- What’s your favorite color? Do you a least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
20- What’s your favorite candy? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
*** Random Questions ***
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
42~ What’s your biggest regret in life?
10- List 5 of your top pet peeves.
9- What’s your favorite season and why? What’s your least favorite?
12- What’s your favorite food? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
7- What are your thoughts on religion? Is there an afterlife?
39~ What are your love languages?
49~ How many times have you been married? Why did they end?
How well do you know me? And some of your thoughts about me
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
How many times do you think you have “made love”?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Do you shave/trim your pubic hair? For you guys do you shave your balls?
What is your favorite toy? Ever wanted to try a specific toy?
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,
4- For a pet, Cat, dog or other?
25~ How do you feel about PDA? (Public Display of Affection)
6- Do you have dreams? Can you remember them? What do you usually dream about?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Family Relation Age Play
7- What if a person smells a certain way? 8- How about smoking?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
48~ Have you ever paid or been paid for sex?
If yes, what?
13~ Is there a difference between, making love, having sex, and fucking?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
* Give a rating for each one (0-100)
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
81~ Do you have any kinks and/or fetishes?
*** What’s Your Favorite…? ***
18~ Who/when was your first “crush”?
53~ How much can you tell me about the one thing you are most passionate about?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
48~ Do you have any siblings? Are you close to your family?
92~ Everyone needs a “safe” word. What is yours?
13- How about having a certain hair cut/style?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
If YES, was it with 2 men or 2 women? Did you enjoy it?
71~ Would you give your partner a hand or foot job? Would you receive one?
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…
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Prisoner/Prison Guard Landlord/Tenant
If you win, what will you make them do?
8- What's your favorite flavor of ice cream? Do you a least favorite?
8- What are your thoughts on politics?
15~ Have you ever been “in love”? Who? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
33- If you could visit any time period, when would you pick? Please explain why?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
12- What is the weirdest thing you've ever eaten?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
1- What’s your favorite animal? Do you a least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Nurse/Patient Celebrity/Fan
10~ How many dates are necessary before you to have sex with someone?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
(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…)
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?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
36~ What is your favorite time of day to have sex/make love?
19- What’s your favorite fairytale? What’s your least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Have you ever? Care to Share?
61~ How willing would you be to try new sexual positions?
Do you watch it? What is your favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
11~ Have you ever been caught by your parents or children or others while having sex?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
82~ Do you have any fantasies involving Role-Playing?
What is your favorite position? Why?
15- What's your favorite saying? What word or phrase is your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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)
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
40~ What’s the weirdest place you’ve ever had sex?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Escort/Client Job Applicant/Hiring Manager
9- Is there something you’ve always wanted to ask me but you’re afraid?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Does the thought excite you? Care to share?
30~ What's something unexpected that turns you on?
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?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Model/Photographer Police/Criminal
Repairman/Lonely Wife Virgin/Experienced
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How many partners have you had oral sex with? Who? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
27- What was/ is nickname? Does it have a meaning behind it?
14- What's your favorite dessert? Do you a least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you have a favorite? Is it ok if your partner does?
Would you allow me to clean every part of your body with my soapy hands and fingers?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
29- How superstitious are you?
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?
19~ Who/when was your first “heartbreak”?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
13- What is the craziest/scariest thing you've ever done?
52~ What are your hobbies?
Would you do it again, and would you rather 2 females or 2 males?
29~ What are some things that turn you off? What is your biggest turn off?
What have you learned about yourself that you did not before this?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
9~ How many times over your lifetime do you think you have had sex so far?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
You know that I will be 100% truthful, so ask.
What’s the longest time you gone without having sex, after, having it? How much time between the others?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
92~ Have you ever had or have an STD? How many? What was it?
Doctor/Nurse Stripper/Client
Would you mind if your partner watched it? How about together vs alone?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
51~ What tends to bring a smile to your face?
How old are you? Male or Female?
1- What was your first impression of me? Has it changed?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
52~ Are you willing to make “those types” of bets with your partner?
36- Do you play video games? What is your favorite? Do you a least favorite?
How about if they talk dirty and/or call you names?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
47~ What would be your dream job and why?
83~ How do you feel about Porn?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
11- How about if they like a certain sports team? 12-How about drinking too much?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
28- What are some things that people do that irritate you?
That one or two things that made you go hmmmm, OMG or wow!
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Do you like it when they show and tell you what they want?
22- What is your favorite childhood memory? What is your least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
19- Do/have you smoked? What do you prefer? How often?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
50~ How many children do you have? What are their ages?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
89~ Do you like taking showers together?
51~ Are you willing to play adult games with your partner?
Do you think this brought you closer together?
76~ Have you had a threesome? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Master/Slave Boss/Maid
7-What do I do in bed that drives you wild? How about, what turns you off?
Would you ever want to be woken up with oral and/or intercourse?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
37- Do you like your name? If you could change it, what would you change it too?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Teacher/Student Stranger/One Night Stand
Would /have you ever given your partner a lap dance and Striptease?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Will you cheat again? How can, you be sure? Define what cheating is to you.
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Would you read them together?
21- What's your favorite way to spend a weekend or time off?
3- Should Pluto still be considered a planet? 4- How about smoking?
32- What's your greatest talent? Can I see it right now?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
13- What’s your favorite drink? What’s your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
22- Do you have any birth marks? How about scars? Care to share how you got them?
45~ How do you feel about me blindfolding you? How about blindfolding me?
84~ How do you feel about reading/listening to adult stories?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
62~ Have you used adult toys?
5- Have you ever been hypnotized? Would you allow yourself to be?
The Ice Breaker Questions
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Over time has your thoughts on sex changed?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
3- What Superhero or Superpower would you want to be/have?
*** Questions About Me ***
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
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?
If you say it, I will stop, and we can talk about it when you are ready.
17- Have you ever done drugs? Which ones? How often?
31- If given a chance to be immortal, would you take it? Why?
17- What’s your favorite holiday? What’s your least favorite?