What is the most interesting question you can ask to get to know someone?
12.06.2025 00:50
*** Deal Breaker Questions ***
33- Beach or Mountains? Or is there another place to like better?
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?
34~ Do you like the lights on or off during sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
9- If you could have three wishes, what would they be? Why?
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?
Get this wrong and this could mean the end… :-) some funny, some not…
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Any that are a turn off?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
Nurse/Patient Celebrity/Fan
'Mountainhead' Is Most-Watched HBO Original Film Since 'Bad Education' - Deadline
Family Relation Age Play
25~ How do you feel about PDA? (Public Display of Affection)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Super Again: UNC Storms Past Oklahoma in NCAA Regional Finale - 247Sports
6- Do you have dreams? Can you remember them? What do you usually dream about?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Rock Icon, 78, Hauled Off Stage in Jaw-Dropping Concert Farewell - Yahoo
37- Do you like your name? If you could change it, what would you change it too?
10~ How many dates are necessary before you to have sex with someone?
If yes, what?
Why does my ex boyfriend do this?
30~ What's something unexpected that turns you on?
11- How about if they like a certain sports team? 12-How about drinking too much?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Suspect in Boulder Molotov attack faces federal hate crime charge - Axios
Will you cheat again? How can, you be sure? Define what cheating is to you.
62~ Have you used adult toys?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
The Hemi V-8 Is Back: ‘We Screwed Up,' Says Ram CEO - Motor1.com
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
28- What are some things that people do that irritate you?
*** Random Questions ***
What is an easy way to get your driver's license?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
21~ What was the best date you ever went on? What has been the worst?
3- Should Pluto still be considered a planet? 4- How about smoking?
Alan Turing's iconic paper on a 'universal computing machine' goes up for auction - Live Science
11~ Have you ever been caught by your parents or children or others while having sex?
23- What is your dream job? What was it as a child?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
How do you weigh in on the Vance-couch conversation?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
The Ice Breaker Questions
13- How about having a certain hair cut/style?
22- What is your favorite childhood memory? What is your least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
18- How often do you drink alcohol? What is your favorite drink?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
18~ Who/when was your first “crush”?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
3- What’s your favorite smell? Do you a least favorite?
89~ Do you like taking showers together?
3- What Superhero or Superpower would you want to be/have?
39~ What are your love languages?
Teacher/Student Stranger/One Night Stand
15~ Have you ever been “in love”? Who? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Model/Photographer Police/Criminal
21- What's your favorite way to spend a weekend or time off?
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?
Prisoner/Prison Guard Landlord/Tenant
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
1- What’s your favorite animal? Do you a least 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…
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”?
49~ How many times have you been married? Why did they end?
If you win, what will you make them do?
45~ How do you feel about me blindfolding you? How about blindfolding me?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
14- What is an embarrassing moment in your life? How about your most embarrassing?
12- What is the weirdest thing you've ever eaten?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
67~ Do you like it when your partner moans and/or is vocal during sex?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
29~ What are some things that turn you off? What is your biggest turn off?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
36- Do you play video games? What is your favorite? Do you a least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
*** Questions About Me ***
83~ How do you feel about Porn?
Master/Slave Boss/Maid
If you say it, I will stop, and we can talk about it when you are ready.
22~ What is the best pickup line anyone has ever used on you? What was the worst?
28~ What are some things that turn on? What is your biggest turn on?
Any that are a turn off?
Would /have you ever given your partner a lap dance and Striptease?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Do you think this brought you closer together?
47~ What would be your dream job and why?
What do you dislike about me? I asked you to be 100% honest.
53~ How much can you tell me about the one thing you are most passionate about?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
5~ When you first started having sex, was it what you thought it would be?
40~ What’s the weirdest place you’ve ever had sex?
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…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
20- What’s your favorite candy? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
51~ What tends to bring a smile to your face?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
52~ What are your hobbies?
7- What if a person smells a certain way? 8- How about smoking?
1~ How old were you when you had your first kiss? Who? Care to Share?
Do you have a favorite? Is it ok if your partner does?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
15- What's your favorite saying? What word or phrase is your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Would you do it again, and would you rather 2 females or 2 males?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
82~ Do you have any fantasies involving Role-Playing?
17- What’s your favorite holiday? What’s your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Escort/Client Job Applicant/Hiring Manager
46~ Have you ever used furniture, or other types of things to aid you while having sex?
31- If given a chance to be immortal, would you take it? Why?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
80~ Share your top three fantasies/desires. (Be detailed) 😊
10- What is your favorite family tradition? What’s your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
5- Have you ever been hypnotized? Would you allow yourself to be?
* Give a rating for each one (0-100)
8- What's your favorite flavor of ice cream? Do you a least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
50~ How many children do you have? What are their ages?
Please share Did you stop?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
13- What’s your favorite drink? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
That one or two things that made you go hmmmm, OMG or wow!
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Would you read them together?
How old are you? Male or Female?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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?
48~ Do you have any siblings? Are you close to your family?
1- What was your first impression of me? Has it changed?
*** Questions about Relationships/Past ***
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
70~ Would/do you have/like anal sex?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
7- What are your thoughts on religion? Is there an afterlife?
9~ How many times over your lifetime do you think you have had sex so far?
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
42~ What’s your biggest regret in life?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
What is your favorite position? Why?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
4- For a pet, Cat, dog or other?
71~ Would you give your partner a hand or foot job? Would you receive one?
27- What was/ is nickname? Does it have a meaning behind it?
If YES, was it with 2 men or 2 women? Did you enjoy it?
11- List at least 5 things on your bucket list. Have you done any of them already?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Do you watch it? What is your favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
92~ Have you ever had or have an STD? How many? What was it?
14- What's your favorite dessert? Do you a least favorite?
How about if they talk dirty and/or call you names?
12- What’s your favorite food? What’s your least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
81~ Do you have any kinks and/or fetishes?
Do you like it when they show and tell you what they want?
Over time has your thoughts on sex changed?
You know that I will be 100% truthful, so ask.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
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,
84~ How do you feel about reading/listening to adult stories?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
10- List 5 of your top pet peeves.
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What have you learned about yourself that you did not before this?
How many partners have you had oral sex with? Who? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
Nothing too Serious
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
61~ How willing would you be to try new sexual positions?
51~ Are you willing to play adult games with your partner?
44~ Care to share something about yourself that no one else knows about you?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
36~ What is your favorite time of day to have sex/make love?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
8- What are your thoughts on politics?
What have you learned about me that was new and/or surprising?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Have you ever? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
19- Do/have you smoked? What do you prefer? How often?
What would you say to prove to yourself that it was really you?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
9- Is there something you’ve always wanted to ask me but you’re afraid?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
I would allow you to do it… What would you do to me?
Would you mind if your partner watched it? How about together vs alone?
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)
What is your favorite toy? Ever wanted to try a specific toy?
19- What’s your favorite fairytale? What’s your least favorite?
How many times do you think you have “made love”?
*** What’s Your Favorite…? ***
29- How superstitious are you?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
How well do you know me? And some of your thoughts about me
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?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Does the thought excite you? Care to share?
2- What’s your favorite color? Do you a least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
What is your view on sex? Meaning, When/Where/ How often/
What was the longest? What was the shortest?
Would you ever want to be woken up with oral and/or intercourse?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you like the “69” position? Do you prefer to be on top or bottom?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
52~ Are you willing to make “those types” of bets with your partner?
38~ Share your most embarrassing sexual memory?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? 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?
17- Have you ever done drugs? Which ones? How often?
34- Ever been to a concert? What was your favorite? Who would you like to see?
9- What’s your favorite season and why? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
13- What is the craziest/scariest thing you've ever done?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
76~ Have you had a threesome? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
32- What's your greatest talent? Can I see it right now?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Doctor/Nurse Stripper/Client
11- What's your favorite restaurant? What’s your least favorite?
(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…)