What is the most interesting question you can ask to get to know someone?
08.06.2025 01:23
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Will you cheat again? How can, you be sure? Define what cheating is to you.
How many partners have you had oral sex with? Who? Care to Share?
‘The Life of Chuck’: Never Mind the Apocalypse, Watch Tom Hiddleston Dance! - Rolling Stone
2- What’s your favorite color? Do you a least favorite?
*** Random Questions ***
24~ What are your expectations in a relationship? (I know a very big question, take your time)
What do men find attractive in an older woman?
52~ What are your hobbies?
67~ Do you like it when your partner moans and/or is vocal during sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Man thought he was 'tired from work' before brain tumour diagnosis - BBC
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
What do you think of Andrew Tate?
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?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
If you were president, how would you make America "great again?"
45~ How do you feel about me blindfolding you? How about blindfolding me?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
37- Do you like your name? If you could change it, what would you change it too?
Liberals, why don't you like Conservatives?
Model/Photographer Police/Criminal
What do you dislike about me? I asked you to be 100% honest.
Would you read them together?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
If YES, was it with 2 men or 2 women? Did you enjoy it?
Do you watch it? What is your favorite?
*** Questions about Relationships/Past ***
48~ Do you have any siblings? Are you close to your family?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
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?
38~ Share your most embarrassing sexual memory?
92~ Have you ever had or have an STD? How many? What was it?
Would you ever want to be woken up with oral and/or intercourse?
Physicists observe a new form of magnetism for the first time - Phys.org
How about if they talk dirty and/or call you names?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
13- How about having a certain hair cut/style?
2025 NCAA baseball bracket: Men's College World Series scores, schedule - NCAA.com
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
3- What’s your favorite smell? Do you a least favorite?
82~ Do you have any fantasies involving Role-Playing?
52~ Are you willing to make “those types” of bets with your partner?
34- Ever been to a concert? What was your favorite? Who would you like to see?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Watch BETA Technologies’ electric aircraft fly into NYC with passengers onboard [Video] - Electrek
36- Do you play video games? What is your favorite? Do you a least favorite?
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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
61~ How willing would you be to try new sexual positions?
Prisoner/Prison Guard Landlord/Tenant
33- If you could visit any time period, when would you pick? Please explain why?
17- Have you ever done drugs? Which ones? How often?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
40~ What’s the weirdest place you’ve ever had sex?
19- Do/have you smoked? What do you prefer? How often?
26~ What side of the bed do you sleep on?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
22~ What is the best pickup line anyone has ever used on you? What was the worst?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
The Ice Breaker Questions
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
33- Beach or Mountains? Or is there another place to like better?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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?
27- What was/ is nickname? Does it have a meaning behind it?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Any that are a turn off?
If you say it, I will stop, and we can talk about it when you are ready.
1~ How old were you when you had your first kiss? Who? Care to Share?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
19- What’s your favorite fairytale? What’s your least favorite?
Do you have a favorite? Is it ok if your partner does?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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- Do you have dreams? Can you remember them? What do you usually dream about?
84~ How do you feel about reading/listening to adult stories?
20- What’s your favorite candy? What’s your least favorite?
49~ How many times have you been married? Why did they end?
70~ Would/do you have/like anal sex?
51~ What tends to bring a smile to your face?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
1- What’s your favorite animal? Do you a least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
What is your favorite toy? Ever wanted to try a specific toy?
28- What are some things that people do that irritate you?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
32- What's your greatest talent? Can I see it right now?
9- What’s your favorite season and why? What’s your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
5- Have you ever been hypnotized? Would you allow yourself to be?
If NO, would you ever have one? Would it be with 2 men or 2 women?
15- What bad habit do you wish you could quit? Do you have any addictions?
50~ How many children do you have? What are their ages?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Doctor/Nurse Stripper/Client
29- How superstitious are you?
How old are you? Male or Female?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
21- What's your favorite way to spend a weekend or time off?
29~ What are some things that turn you off? What is your biggest turn off?
89~ Do you like taking showers together?
What was the longest? What was the shortest?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
13- What’s your favorite drink? What’s your least favorite?
18- How often do you drink alcohol? What is your favorite drink?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
10- What is your favorite family tradition? What’s your least favorite?
Please share Did you stop?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
25~ How do you feel about PDA? (Public Display of Affection)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
39~ What are your love languages?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
81~ Do you have any kinks and/or fetishes?
Would you mind if your partner watched it? How about together vs alone?
Any that are a turn off?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
23- What is your dream job? What was it as a child?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
36~ What is your favorite time of day to have sex/make love?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
How well do you know me? And some of your thoughts about me
51~ Are you willing to play adult games with your partner?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Do you think this brought you closer together?
11- How about if they like a certain sports team? 12-How about drinking too much?
Nothing too Serious
Can you Deep Throat? Do you like the taste of yourself?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Nurse/Patient Celebrity/Fan
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
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,
28~ What are some things that turn on? What is your biggest turn on?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
92~ Everyone needs a “safe” word. What is yours?
7- What are your thoughts on religion? Is there an afterlife?
13- What is the craziest/scariest thing you've ever done?
71~ Would you give your partner a hand or foot job? Would you receive one?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
83~ How do you feel about Porn?
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
22- Do you have any birth marks? How about scars? Care to share how you got them?
48~ Have you ever paid or been paid for sex?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
47~ What would be your dream job and why?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
31- If given a chance to be immortal, would you take it? Why?
15- What's your favorite saying? What word or phrase is your least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
You know that I will be 100% truthful, so ask.
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Have you ever? Care to Share?
4- For a pet, Cat, dog or other?
Family Relation Age Play
What have you learned about me that was new and/or surprising?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
14- What is an embarrassing moment in your life? How about your most embarrassing?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Would you do it again, and would you rather 2 females or 2 males?
(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…)
62~ Have you used adult toys?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
What is your favorite position? Why?
1- What was your first impression of me? Has it changed?
15~ Have you ever been “in love”? Who? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Would you allow me to clean every part of your body with my soapy hands and fingers?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
30~ What's something unexpected that turns you on?
7- What if a person smells a certain way? 8- How about smoking?
What would you say to prove to yourself that it was really you?
76~ Have you had a threesome? Care to Share?
Does the thought excite you? Care to share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Do you like it when they show and tell you what they want?
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?
If you win, what will you make them do?
3- What Superhero or Superpower would you want to be/have?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
14- What's your favorite dessert? Do you a least favorite?
What have you learned about yourself that you did not before this?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Escort/Client Job Applicant/Hiring Manager
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…
12- What’s your favorite food? What’s your least favorite?
18~ Who/when was your first “crush”?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
*** Questions About Me ***
3- Should Pluto still be considered a planet? 4- How about smoking?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
10~ How many dates are necessary before you to have sex with someone?
Would /have you ever given your partner a lap dance and Striptease?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How many times do you think you have “made love”?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
42~ What’s your biggest regret in life?
13~ Is there a difference between, making love, having sex, and fucking?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
I would allow you to do it… What would you do to me?
21~ What was the best date you ever went on? What has been the worst?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
17- What’s your favorite holiday? What’s your least favorite?
*** Deal Breaker Questions ***
Over time has your thoughts on sex changed?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
5~ When you first started having sex, was it what you thought it would be?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
22- What is your favorite childhood memory? What is your least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
If yes, what?
65~ Describe the best orgasm you’ve ever had? Care to share?
9~ How many times over your lifetime do you think you have had sex so far?
11~ Have you ever been caught by your parents or children or others while having sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
9- If you could have three wishes, what would they be? Why?
* Give a rating for each one (0-100)
10- List 5 of your top pet peeves.
That one or two things that made you go hmmmm, OMG or wow!
34~ Do you like the lights on or off during sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
Master/Slave Boss/Maid
8- What are your thoughts on politics?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
12- What is the weirdest thing you've ever eaten?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Teacher/Student Stranger/One Night Stand
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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~ Who/when was your first “heartbreak”?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Do you like the “69” position? Do you prefer to be on top or bottom?
80~ Share your top three fantasies/desires. (Be detailed) 😊
44~ Care to share something about yourself that no one else knows about you?
*** What’s Your Favorite…? ***