What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 12:31
33- If you could visit any time period, when would you pick? Please explain why?
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?
Weed Could Be Wrecking Your Heart – Study Uncovers Dangers of Smoking and Edibles - SciTechDaily
50~ How many children do you have? What are their ages?
19~ Who/when was your first “heartbreak”?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Olfactory neurons use unexpected 'solid' clusters to achieve genetic precision - Phys.org
52~ Are you willing to make “those types” of bets with your partner?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
36~ What is your favorite time of day to have sex/make love?
Will you cheat again? How can, you be sure? Define what cheating is to you.
31- If given a chance to be immortal, would you take it? Why?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Woman banned for life from cruise after 'breaking rule' she shared on social media - LADbible
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Would you ever want to be woken up with oral and/or intercourse?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
IO Interactive Reveals 007 First Light, Full Trailer Out This Week - Game Informer
17- Have you ever done drugs? Which ones? How often?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Nurse/Patient Celebrity/Fan
Turns Out, AI Gobbles Up a Lot of Energy - Newser
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
29~ What are some things that turn you off? What is your biggest turn off?
(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…)
34~ Do you like the lights on or off during sex?
I just cannot wake up early, even if I sleep on time. What should I do?
Do you think this brought you closer together?
76~ Have you had a threesome? Care to Share?
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…
Xbox sale round-up June 24, 2025 - DLC - TrueAchievements
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Nothing too Serious
How old are you? Male or Female?
What is the cost of implementing synchronized traffic lights in a mid-sized city?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What baseball stories from the early days of the sport seem too bizarre to be true?
4- For a pet, Cat, dog or other?
33- Beach or Mountains? Or is there another place to like better?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
23- What is your dream job? What was it as a child?
10- List 5 of your top pet peeves.
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
3- What’s your favorite smell? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
52~ What are your hobbies?
Any that are a turn off?
34- Ever been to a concert? What was your favorite? Who would you like to see?
9- If you could have three wishes, what would they be? Why?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
5- Have you ever been hypnotized? Would you allow yourself to be?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
12- What’s your favorite food? What’s your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What do you dislike about me? I asked you to be 100% honest.
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
40~ What’s the weirdest place you’ve ever had sex?
Over time has your thoughts on sex changed?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
12- What is the weirdest thing you've ever eaten?
What have you learned about me that was new and/or surprising?
If YES, was it with 2 men or 2 women? Did you enjoy it?
If you win, what will you make them do?
Doctor/Nurse Stripper/Client
Would you allow me to clean every part of your body with my soapy hands and fingers?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
10- What is your favorite family tradition? What’s your least favorite?
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?
15~ Have you ever been “in love”? Who? Care to Share?
Do you have a favorite? Is it ok if your partner does?
5~ When you first started having sex, was it what you thought it would be?
Can you Deep Throat? Do you like the taste of yourself?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Escort/Client Job Applicant/Hiring Manager
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Repairman/Lonely Wife Virgin/Experienced
Would you mind if your partner watched it? How about together vs alone?
71~ Would you give your partner a hand or foot job? Would you receive one?
84~ How do you feel about reading/listening to adult stories?
17- What’s your favorite holiday? What’s your least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
Please share Did you stop?
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…
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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?
61~ How willing would you be to try new sexual positions?
13- What’s your favorite drink? What’s your least favorite?
* Give a rating for each one (0-100)
7- What if a person smells a certain way? 8- How about smoking?
Would you do it again, and would you rather 2 females or 2 males?
20- What’s your favorite candy? What’s your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
9- Is there something you’ve always wanted to ask me but you’re afraid?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
How well do you know me? And some of your thoughts about me
6- Do you have dreams? Can you remember them? What do you usually dream about?
What would you say to prove to yourself that it was really you?
21~ What was the best date you ever went on? What has been the worst?
8- What are your thoughts on politics?
51~ Are you willing to play adult games with your partner?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
60~ How important is oral sex? Do you like receiving? Do you like giving?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
22- What is your favorite childhood memory? What is your least favorite?
48~ Have you ever paid or been paid for sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
27- What was/ is nickname? Does it have a meaning behind it?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
89~ Do you like taking showers together?
Does the thought excite you? Care to share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
Family Relation Age Play
25~ How do you feel about PDA? (Public Display of Affection)
13- What is the craziest/scariest thing you've ever done?
11- How about if they like a certain sports team? 12-How about drinking too much?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
11~ Have you ever been caught by your parents or children or others while having sex?
How many partners have you had oral sex with? Who? Care to Share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
19- Do/have you smoked? What do you prefer? How often?
How many times do you think you have “made love”?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Would you read them together?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
44~ Care to share something about yourself that no one else knows about you?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
*** Questions About Me ***
15- What bad habit do you wish you could quit? Do you have any addictions?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
What is your favorite toy? Ever wanted to try a specific toy?
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?
39~ What are your love languages?
Teacher/Student Stranger/One Night Stand
37- Do you like your name? If you could change it, what would you change it too?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
I would allow you to do it… What would you do to me?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What is your view on sex? Meaning, When/Where/ How often/
You know that I will be 100% truthful, so ask.
29- How superstitious are you?
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?
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?
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
1- What’s your favorite animal? Do you a least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
9- What’s your favorite season and why? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
That one or two things that made you go hmmmm, OMG or wow!
Will you kiss after your partner has gone down on you? Swallow or spit semen?
3- What Superhero or Superpower would you want to be/have?
*** Questions about Relationships/Past ***
Do you like it when they show and tell you what they want?
*** Random Questions ***
10~ How many dates are necessary before you to have sex with someone?
92~ Everyone needs a “safe” word. What is yours?
15- What's your favorite saying? What word or phrase is your least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
Master/Slave Boss/Maid
Do you watch it? What is your favorite?
2- What’s your favorite color? Do you a least favorite?
What have you learned about yourself that you did not before this?
Would /have you ever given your partner a lap dance and Striptease?
47~ What would be your dream job and why?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
*** What’s Your Favorite…? ***
42~ What’s your biggest regret in life?
83~ How do you feel about Porn?
38~ Share your most embarrassing sexual memory?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
18- How often do you drink alcohol? What is your favorite drink?
82~ Do you have any fantasies involving Role-Playing?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
If yes, what?
62~ Have you used adult toys?
26~ What side of the bed do you sleep on?
Model/Photographer Police/Criminal
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
35- Do you like playing board or cards game? What is your favorite? 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?
14- What's your favorite dessert? 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…
1- What was your first impression of me? Has it changed?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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,
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
81~ Do you have any kinks and/or fetishes?
22- Do you have any birth marks? How about scars? Care to share how you got them?
30~ What's something unexpected that turns you on?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
The Ice Breaker Questions
92~ Have you ever had or have an STD? How many? What was it?
7- What are your thoughts on religion? Is there an afterlife?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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?
70~ Would/do you have/like anal sex?
18~ Who/when was your first “crush”?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
48~ Do you have any siblings? Are you close to your family?
Any that are a turn off?
32- What's your greatest talent? Can I see it right now?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Do you like the “69” position? Do you prefer to be on top or bottom?
*** Deal Breaker Questions ***
19- What’s your favorite fairytale? What’s your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
51~ What tends to bring a smile to your face?
14- What is an embarrassing moment in your life? How about your most embarrassing?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
28~ What are some things that turn on? What is your biggest turn on?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
8- What's your favorite flavor of ice cream? Do you a least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
1~ How old were you when you had your first kiss? Who? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
How about if they talk dirty and/or call you names?
49~ How many times have you been married? Why did they end?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
What was the longest? What was the shortest?
What is your favorite position? Why?
65~ Describe the best orgasm you’ve ever had? Care to share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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)