What is the most interesting question you can ask to get to know someone?
10.06.2025 00:31
Teacher/Student Stranger/One Night Stand
4- For a pet, Cat, dog or other?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
What are some reasons why men may not want to date a woman who can pay her own bills?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Do you watch it? What is your favorite?
92~ Have you ever had or have an STD? How many? What was it?
Why are daughters mean to their mothers?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
65~ Describe the best orgasm you’ve ever had? Care to share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Why does a straight man like anal penetration?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
I would allow you to do it… What would you do to me?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
WWDC 2025: What to Expect From macOS 26 Tahoe - MacRumors
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
11- What's your favorite restaurant? What’s your least favorite?
How do you get a girl to like you?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
10- List 5 of your top pet peeves.
Have you ever? Care to Share?
Who is the greatest light welterweight boxer of all time?
83~ How do you feel about Porn?
7- What are your thoughts on religion? Is there an afterlife?
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?
What was it like being spanked as a kid?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What would you say to prove to yourself that it was really you?
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?
Gina Ortiz Jones, a Progressive, Is Elected San Antonio’s Mayor - The New York Times
12- What’s your favorite food? What’s your least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
71~ Would you give your partner a hand or foot job? Would you receive one?
(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…)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
8- What are your thoughts on politics?
Have you ever gone to a porn theater with your wife?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
9- If you could have three wishes, what would they be? Why?
14- What is an embarrassing moment in your life? How about your most embarrassing?
8- What's your favorite flavor of ice cream? Do you a least favorite?
40~ What’s the weirdest place you’ve ever had sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
67~ Do you like it when your partner moans and/or is vocal during sex?
How many times do you think you have “made love”?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
48~ Have you ever paid or been paid for sex?
18~ Who/when was your first “crush”?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Would you ever want to be woken up with oral and/or intercourse?
47~ What would be your dream job and why?
If you win, what will you make them do?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
80~ Share your top three fantasies/desires. (Be detailed) 😊
What is your favorite toy? Ever wanted to try a specific toy?
Please share Did you stop?
Do you like the “69” position? Do you prefer to be on top or bottom?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
26~ What side of the bed do you sleep on?
Escort/Client Job Applicant/Hiring Manager
Nurse/Patient Celebrity/Fan
37- Do you like your name? If you could change it, what would you change it too?
30~ What's something unexpected that turns you on?
Any that are a turn off?
5~ When you first started having sex, was it what you thought it would be?
50~ How many children do you have? What are their ages?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
15- What's your favorite saying? What word or phrase is your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
33- If you could visit any time period, when would you pick? Please explain why?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Nothing too Serious
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
How about if they talk dirty and/or call you names?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
1- What was your first impression of me? Has it changed?
45~ How do you feel about me blindfolding you? How about blindfolding me?
21~ What was the best date you ever went on? What has been the worst?
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…
3- What Superhero or Superpower would you want to be/have?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
23- What is your dream job? What was it as a child?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Will you cheat again? How can, you be sure? Define what cheating is to you.
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
13- What is the craziest/scariest thing you've ever done?
31- If given a chance to be immortal, would you take it? Why?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
34~ Do you like the lights on or off during sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
15~ Have you ever been “in love”? Who? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
What have you learned about me that was new and/or surprising?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
10- What is your favorite family tradition? What’s your least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
7- What if a person smells a certain way? 8- How about smoking?
Would /have you ever given your partner a lap dance and Striptease?
What was the longest? What was the shortest?
70~ Would/do you have/like anal sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
11- List at least 5 things on your bucket list. Have you done any of them already?
36- Do you play video games? What is your favorite? Do you a least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
25~ How do you feel about PDA? (Public Display of Affection)
7- What’s your favorite book? Do you have a favorite genre? 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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
*** Deal Breaker Questions ***
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
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 allow me to clean every part of your body with my soapy hands and fingers?
84~ How do you feel about reading/listening to adult stories?
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?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
*** Questions about Relationships/Past ***
52~ What are your hobbies?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
39~ What are your love languages?
*** Questions About Me ***
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What is your view on sex? Meaning, When/Where/ How often/
28- What are some things that people do that irritate you?
6- Do you have dreams? Can you remember them? What do you usually dream about?
20- What’s your favorite candy? What’s your least favorite?
19- Do/have you smoked? What do you prefer? How often?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
12- What is the weirdest thing you've ever eaten?
Doctor/Nurse Stripper/Client
61~ How willing would you be to try new sexual positions?
44~ Care to share something about yourself that no one else knows about you?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Family Relation Age Play
*** What’s Your Favorite…? ***
5- Have you ever been hypnotized? Would you allow yourself to be?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Would you do it again, and would you rather 2 females or 2 males?
* Give a rating for each one (0-100)
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
What is your favorite position? Why?
What do you dislike about me? I asked you to be 100% honest.
1~ How old were you when you had your first kiss? Who? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
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…
Do you shave/trim your pubic hair? For you guys do you shave your balls?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
51~ What tends to bring a smile to your face?
10~ How many dates are necessary before you to have sex with someone?
60~ How important is oral sex? Do you like receiving? Do you like giving?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
17- Have you ever done drugs? Which ones? How often?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Master/Slave Boss/Maid
Would you read them together?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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?
How many partners have you had oral sex with? Who? Care to Share?
49~ How many times have you been married? Why did they end?
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…
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)
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
62~ Have you used adult toys?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Can you Deep Throat? Do you like the taste of yourself?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
*** Random Questions ***
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
38~ Share your most embarrassing sexual memory?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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?
You know that I will be 100% truthful, so ask.
92~ Everyone needs a “safe” word. What is yours?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
48~ Do you have any siblings? Are you close to your family?
11~ Have you ever been caught by your parents or children or others while having sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
If NO, would you ever have one? Would it be with 2 men or 2 women?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Any that are a turn off?
27- What was/ is nickname? Does it have a meaning behind 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?
82~ Do you have any fantasies involving Role-Playing?
3- Should Pluto still be considered a planet? 4- How about smoking?
18- How often do you drink alcohol? What is your favorite drink?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
9~ How many times over your lifetime do you think you have had sex so far?
13- How about having a certain hair cut/style?
22- What is your favorite childhood memory? What is your least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
That one or two things that made you go hmmmm, OMG or wow!
Over time has your thoughts on sex changed?
Do you have a favorite? Is it ok if your partner does?
If yes, what?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
13~ Is there a difference between, making love, having sex, and fucking?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
11- How about if they like a certain sports team? 12-How about drinking too much?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
53~ How much can you tell me about the one thing you are most passionate about?
3- What’s your favorite smell? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
36~ What is your favorite time of day to have sex/make love?
33- Beach or Mountains? Or is there another place to like better?
76~ Have you had a threesome? Care to Share?
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,
32- What's your greatest talent? Can I see it right now?
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?
How well do you know me? And some of your thoughts about me
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
What have you learned about yourself that you did not before this?
28~ What are some things that turn on? What is your biggest turn on?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Does the thought excite you? Care to share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Would you mind if your partner watched it? How about together vs alone?
Do you think this brought you closer together?
52~ Are you willing to make “those types” of bets with your partner?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
89~ Do you like taking showers together?
81~ Do you have any kinks and/or fetishes?
Do you like it when they show and tell you what they want?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
7-What do I do in bed that drives you wild? How about, what turns you off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
How old are you? Male or Female?
29- How superstitious are you?
If you say it, I will stop, and we can talk about it when you are ready.
1- What’s your favorite animal? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
2- What’s your favorite color? Do you a least favorite?
21- What's your favorite way to spend a weekend or time off?
34- Ever been to a concert? What was your favorite? Who would you like to see?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
17- What’s your favorite holiday? What’s your least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
The Ice Breaker Questions
42~ What’s your biggest regret in life?
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
51~ Are you willing to play adult games with your partner?
Model/Photographer Police/Criminal
19~ Who/when was your first “heartbreak”?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?