What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 01:32

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