What is the most interesting question you can ask to get to know someone?
10.06.2025 08:15
What is your favorite toy? Ever wanted to try a specific toy?
How well do you know me? And some of your thoughts about me
Repairman/Lonely Wife Virgin/Experienced
How has your life changed since starting college?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Can being annoyed be a sign of getting angry?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
11- What's your favorite restaurant? What’s your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
How do people break a narcissist man's ego?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
PSA: You Probably Don't Need To Be Weighed At The Doctor's Office - HuffPost
14- What's your favorite dessert? Do you a least favorite?
Over time has your thoughts on sex changed?
17- Have you ever done drugs? Which ones? How often?
'Mission: Impossible 8': Inside How They Shot Underwater Submarine - IndieWire
4- For a pet, Cat, dog or other?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What is your favorite position? Why?
Derek Jeter Shares Brutal Reality for Yankees After Dodgers Loss - Sports Illustrated
If NO, would you ever have one? Would it be with 2 men or 2 women?
Will you cheat again? How can, you be sure? Define what cheating is to you.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
How do empaths destroy narcissists?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
90~ Have you ever had sex in a Pool or Hot Tub? Would 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,
2025 Stanley Cup Finals Preview: Can Connor McDavid Finally Do It? - The Ringer
31- If given a chance to be immortal, would you take it? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?
33- Beach or Mountains? Or is there another place to like better?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Enhanced Box Score: Cubs 2, Reds 0 – May 31, 2025 - Bleacher Nation
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Get this wrong and this could mean the end… :-) some funny, some not…
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Father’s Day 2025: 28 gifts dads will actually want - The Verge
Do you have a favorite? Is it ok if your partner does?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Model/Photographer Police/Criminal
62~ Have you used adult toys?
76~ Have you had a threesome? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How do you stop your balls from sweating?
Teacher/Student Stranger/One Night Stand
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
13- What’s your favorite drink? What’s your least favorite?
37- Do you like your name? If you could change it, what would you change it too?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
That one or two things that made you go hmmmm, OMG or wow!
92~ Everyone needs a “safe” word. What is yours?
How many times do you think you have “made love”?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
7- What are your thoughts on religion? Is there an afterlife?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
Do you watch it? What is your favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
15~ Have you ever been “in love”? Who? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
38~ Share your most embarrassing sexual memory?
19- Do/have you smoked? What do you prefer? How often?
23- What is your dream job? What was it as a child?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Would you do it again, and would you rather 2 females or 2 males?
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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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)
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?
13- How about having a certain hair cut/style?
9- What’s your favorite season and why? What’s your least favorite?
Any that are a turn off?
19~ Who/when was your first “heartbreak”?
2- What’s your favorite color? Do you a least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
28~ What are some things that turn on? What is your biggest turn on?
10- What is your favorite family tradition? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
Nurse/Patient Celebrity/Fan
What is your view on sex? Meaning, When/Where/ How often/
15- What's your favorite saying? What word or phrase is your least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
15- What bad habit do you wish you could quit? Do you have any addictions?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
*** What’s Your Favorite…? ***
What do you dislike about me? I asked you to be 100% honest.
Can you Deep Throat? Do you like the taste of yourself?
52~ What are your hobbies?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Would you ever want to be woken up with oral and/or intercourse?
8- What are your thoughts on politics?
3- Should Pluto still be considered a planet? 4- How about smoking?
(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…)
19- What’s your favorite fairytale? What’s your least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
I would allow you to do it… What would you do to me?
17- What’s your favorite holiday? What’s your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
*** Random Questions ***
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
51~ What tends to bring a smile to your face?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
50~ How many children do you have? What are their ages?
If yes, what?
18~ Who/when was your first “crush”?
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…
Do you like it when they show and tell you what they want?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Escort/Client Job Applicant/Hiring Manager
25~ How do you feel about PDA? (Public Display of Affection)
* Give a rating for each one (0-100)
53~ How much can you tell me about the one thing you are most passionate about?
34- Ever been to a concert? What was your favorite? Who would you like to see?
47~ What would be your dream job and why?
82~ Do you have any fantasies involving Role-Playing?
52~ Are you willing to make “those types” of bets with your partner?
If you win, what will you make them do?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
The Ice Breaker Questions
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?
1- What’s your favorite animal? Do you a least favorite?
Would you mind if your partner watched it? How about together vs alone?
How about if they talk dirty and/or call you names?
If you say it, I will stop, and we can talk about it when you are ready.
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
30~ What's something unexpected that turns you on?
13- What is the craziest/scariest thing you've ever done?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Do you think this brought you closer together?
84~ How do you feel about reading/listening to adult stories?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
20- What’s your favorite candy? What’s your least favorite?
48~ Have you ever paid or been paid for sex?
11~ Have you ever been caught by your parents or children or others while having sex?
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?
44~ Care to share something about yourself that no one else knows about you?
1- What was your first impression of me? Has it changed?
Please share Did you stop?
Master/Slave Boss/Maid
21~ What was the best date you ever went on? What has been the worst?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Would you allow me to clean every part of your body with my soapy hands and fingers?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
22- Do you have any birth marks? How about scars? Care to share how you got them?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
61~ How willing would you be to try new sexual positions?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
What have you learned about me that was new and/or surprising?
28- What are some things that people do that irritate you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Does the thought excite you? Care to share?
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?
89~ Do you like taking showers together?
How old are you? Male or Female?
9~ How many times over your lifetime do you think you have had sex so far?
36~ What is your favorite time of day to have sex/make love?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
11- List at least 5 things on your bucket list. Have you done any of them already?
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…
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
18- How often do you drink alcohol? What is your favorite drink?
32- What's your greatest talent? Can I see it right now?
Nothing too Serious
81~ Do you have any kinks and/or fetishes?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Would you read them together?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
29- How superstitious are you?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Any that are a turn off?
*** Deal Breaker Questions ***
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
29~ What are some things that turn you off? What is your biggest turn off?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
21- What's your favorite way to spend a weekend or time off?
45~ How do you feel about me blindfolding you? How about blindfolding me?
1~ How old were you when you had your first kiss? Who? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
7-What do I do in bed that drives you wild? How about, what turns you off?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
3- What’s your favorite smell? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
65~ Describe the best orgasm you’ve ever had? Care to share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
70~ Would/do you have/like anal sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Family Relation Age Play
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
27- What was/ is nickname? Does it have a meaning behind it?
51~ Are you willing to play adult games with your partner?
5- Have you ever been hypnotized? Would you allow yourself to be?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
9- If you could have three wishes, what would they be? Why?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
You know that I will be 100% truthful, so ask.
Prisoner/Prison Guard Landlord/Tenant
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
What have you learned about yourself that you did not before this?
Would /have you ever given your partner a lap dance and Striptease?
36- Do you play video games? What is your favorite? Do you a least favorite?
10- List 5 of your top pet peeves.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Have you ever? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
6- Do you have dreams? Can you remember them? What do you usually dream about?
26~ What side of the bed do you sleep on?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
3- What Superhero or Superpower would you want to be/have?
7- What if a person smells a certain way? 8- How about smoking?
*** Questions about Relationships/Past ***
5~ When you first started having sex, was it what you thought it would be?
34~ Do you like the lights on or off during sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
*** Questions About Me ***
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?
22- What is your favorite childhood memory? What is your least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
How many partners have you had oral sex with? Who? Care to Share?
12- What is the weirdest thing you've ever eaten?
What would you say to prove to yourself that it was really you?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
42~ What’s your biggest regret in life?
12- What’s your favorite food? What’s your least favorite?
39~ What are your love languages?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
11- How about if they like a certain sports team? 12-How about drinking too much?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
49~ How many times have you been married? Why did they end?
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?
48~ Do you have any siblings? Are you close to your family?
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?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
83~ How do you feel about Porn?
Doctor/Nurse Stripper/Client