What is the most interesting question you can ask to get to know someone?
Last Updated: 03.07.2025 04:05

49~ If you could, would you want to be the opposite sex for a day, week, or year?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
The Hemi V-8 Is Back: ‘We Screwed Up,' Says Ram CEO - Motor1.com
*** Random Questions ***
23- What is your dream job? What was it as a child?
How well do you know me? And some of your thoughts about me
The Best Tech Gifts for Father’s Day 2025 - Gizmodo
Do you have a favorite? Is it ok if your partner does?
Have you ever? Care to Share?
18~ Who/when was your first “crush”?
Broncos 2025 minicamp takeaways - Mile High Report
What have you learned about me that was new and/or surprising?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
The BEST exercise for heart health, according to top US cardiac surgeon - Times of India
3- What was the most surprising thing you’ve learned about me throughout our relationship?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
13- How about having a certain hair cut/style?
What did your sister do to you that you can never forget?
10- List 5 of your top pet peeves.
7-What do I do in bed that drives you wild? How about, what turns you off?
10- What is your favorite family tradition? What’s your least favorite?
Why do narcissists want to hurt your feelings, even after they discard you?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
US Steel workers see hope of job security in deal with Japan’s Nippon - Financial Times
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?
Get this wrong and this could mean the end… :-) some funny, some not…
61~ How willing would you be to try new sexual positions?
Stop Work Orders At NASA JPL - NASA Watch
1- What was your first impression of me? Has it changed?
7- What if a person smells a certain way? 8- How about smoking?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Are there many people here who suffer from schizophrenia?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Can you Deep Throat? Do you like the taste of yourself?
34- Ever been to a concert? What was your favorite? Who would you like to see?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
Bitcoin (BTC) Price Climbs After Trump Tells GOP Not to Worry About Deficit Spending - CoinDesk
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
11- List at least 5 things on your bucket list. Have you done any of them already?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
81~ Do you have any kinks and/or fetishes?
Prisoner/Prison Guard Landlord/Tenant
Do you shave/trim your pubic hair? For you guys do you shave your balls?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
42~ What’s your biggest regret in life?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
48~ Have you ever paid or been paid for sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
33- Beach or Mountains? Or is there another place to like better?
Would you mind if your partner watched it? How about together vs alone?
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?
70~ Would/do you have/like anal sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
*** Questions about Relationships/Past ***
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
53~ How much can you tell me about the one thing you are most passionate about?
47~ What would be your dream job and why?
*** What’s Your 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…
14- What's your favorite dessert? Do you a least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
40~ What’s the weirdest place you’ve ever had sex?
11~ Have you ever been caught by your parents or children or others while having sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
7- What are your thoughts on religion? Is there an afterlife?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
8- What's your favorite flavor of ice cream? Do you a least favorite?
If you win, what will you make them do?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What is your favorite toy? Ever wanted to try a specific toy?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
31- If given a chance to be immortal, would you take it? Why?
36- Do you play video games? What is your favorite? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
5~ When you first started having sex, was it what you thought it would be?
19- What’s your favorite fairytale? What’s your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
32- What's your greatest talent? Can I see it right now?
If yes, what?
20- What’s your favorite candy? What’s your least favorite?
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
21- What's your favorite way to spend a weekend or time off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
2- What’s your favorite color? Do you a least favorite?
22- What is your favorite childhood memory? What is your least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
89~ Do you like taking showers together?
92~ Have you ever had or have an STD? How many? What was it?
36~ What is your favorite time of day to have sex/make love?
11- How about if they like a certain sports team? 12-How about drinking too much?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Do you watch it? What is your favorite?
21~ What was the best date you ever went on? What has been the worst?
How many partners have you had oral sex with? Who? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
84~ How do you feel about reading/listening to adult stories?
5- Have you ever been hypnotized? Would you allow yourself to be?
How old are you? Male or Female?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
18- How often do you drink alcohol? What is your favorite drink?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would you allow me to clean every part of your body with my soapy hands and fingers?
44~ Care to share something about yourself that no one else knows about you?
Does the thought excite you? Care to share?
34~ Do you like the lights on or off during sex?
I would allow you to do it… What would you do to me?
45~ How do you feel about me blindfolding you? How about blindfolding me?
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,
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
If NO, would you ever have one? Would it be with 2 men or 2 women?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Family Relation Age Play
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)
10~ How many dates are necessary before you to have sex with someone?
62~ Have you used adult toys?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Escort/Client Job Applicant/Hiring Manager
51~ What tends to bring a smile to your face?
Repairman/Lonely Wife Virgin/Experienced
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
9- What’s your favorite season and why? What’s your least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
(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…)
83~ How do you feel about Porn?
9- If you could have three wishes, what would they be? Why?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you think this brought you closer together?
13- What’s your favorite drink? What’s your least favorite?
*** Questions About Me ***
52~ What are your hobbies?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
11- What's your favorite restaurant? What’s your least favorite?
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?
What would you say to prove to yourself that it was really you?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Model/Photographer Police/Criminal
The Ice Breaker Questions
52~ Are you willing to make “those types” of bets with your partner?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
Nothing too Serious
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Will you cheat again? How can, you be sure? Define what cheating is to you.
6- Do you have dreams? Can you remember them? What do you usually dream about?
67~ Do you like it when your partner moans and/or is vocal during sex?
Would you read them together?
How about if they talk dirty and/or call you names?
What was the longest? What was the shortest?
71~ Would you give your partner a hand or foot job? Would you receive one?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
26~ What side of the bed do you sleep on?
39~ What are your love languages?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
17- What’s your favorite holiday? What’s your 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…
If you say it, I will stop, and we can talk about it when you are ready.
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
29- How superstitious are you?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
1- What’s your favorite animal? Do you a least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
51~ Are you willing to play adult games with your partner?
15- What's your favorite saying? What word or phrase is your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
12- What’s your favorite food? What’s your least favorite?
Doctor/Nurse Stripper/Client
27- What was/ is nickname? Does it have a meaning behind it?
19- Do/have you smoked? What do you prefer? How often?
What is your view on sex? Meaning, When/Where/ How often/
Any that are a turn off?
Please share Did you stop?
You know that I will be 100% truthful, so ask.
82~ Do you have any fantasies involving Role-Playing?
37- Do you like your name? If you could change it, what would you change it too?
Do you like it when they show and tell you what they want?
Would you ever want to be woken up with oral and/or intercourse?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
*** Deal Breaker Questions ***
Do you like the “69” position? Do you prefer to be on top or bottom?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Any that are a turn off?
76~ Have you had a threesome? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
92~ Everyone needs a “safe” word. What is yours?
15- What bad habit do you wish you could quit? Do you have any addictions?
29~ What are some things that turn you off? What is your biggest turn off?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
* Give a rating for each one (0-100)
25~ How do you feel about PDA? (Public Display of Affection)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
28- What are some things that people do that irritate you?
17- Have you ever done drugs? Which ones? How often?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
50~ How many children do you have? What are their ages?
80~ Share your top three fantasies/desires. (Be detailed) 😊
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Over time has your thoughts on sex changed?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
3- What’s your favorite smell? Do you a least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
3- What Superhero or Superpower would you want to be/have?
That one or two things that made you go hmmmm, OMG or wow!
What is your favorite position? Why?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
8- What are your thoughts on politics?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
1~ How old were you when you had your first kiss? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
12- What is the weirdest thing you've ever eaten?
What have you learned about yourself that you did not before this?
What do you dislike about me? I asked you to be 100% honest.
If YES, was it with 2 men or 2 women? Did you enjoy it?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
48~ Do you have any siblings? Are you close to your family?
28~ What are some things that turn on? What is your biggest turn on?
30~ What's something unexpected that turns you on?
Would you do it again, and would you rather 2 females or 2 males?
Would /have you ever given your partner a lap dance and Striptease?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
13~ Is there a difference between, making love, having sex, and fucking?
Master/Slave Boss/Maid
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
13- What is the craziest/scariest thing you've ever done?
3- Should Pluto still be considered a planet? 4- How about smoking?
19~ Who/when was your first “heartbreak”?
38~ Share your most embarrassing sexual memory?
14- What is an embarrassing moment in your life? How about your most embarrassing?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
How many times do you think you have “made love”?
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?
Teacher/Student Stranger/One Night Stand
4- For a pet, Cat, dog or other?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
49~ How many times have you been married? Why did they end?
33- If you could visit any time period, when would you pick? Please explain why?
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?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?