What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 02:38
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
28- What are some things that people do that irritate you?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What are your thoughts on RM's new album "Right Place, Wrong Person"?
How about if they talk dirty and/or call you names?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
82~ Do you have any fantasies involving Role-Playing?
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64~ When was your very first orgasm? When was your first from having sex? Care to share?
71~ Would you give your partner a hand or foot job? Would you receive one?
33- If you could visit any time period, when would you pick? Please explain why?
What is Rejuran treatment, and how does it benefit the skin?
7- What if a person smells a certain way? 8- How about smoking?
13- What’s your favorite drink? What’s your least favorite?
29- How superstitious are you?
Is the Las Vegas Grand Prix considered one of the "premier events on the Formula 1 calendar?"
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
92~ Everyone needs a “safe” word. What is yours?
Doctor/Nurse Stripper/Client
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12- What’s your favorite food? What’s your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Possible GPD Win 5 spotted running AMD Ryzen AI Max+ 395 'Strix Halo' APU - Notebookcheck
26~ What side of the bed do you sleep on?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
Cher’s son Elijah Blue Allman hospitalized after drug overdose: report - Page Six
If NO, would you ever have one? Would it be with 2 men or 2 women?
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?
19- What’s your favorite fairytale? What’s your least favorite?
‘Stronger’ and ‘On Muscle’: What Goes to Work When We Work Out - WSJ
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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…
65~ Describe the best orgasm you’ve ever had? Care to share?
‘Gas station heroin’ is technically illegal and widely available. Here are the facts - WANE 15
What was the longest? What was the shortest?
Teacher/Student Stranger/One Night Stand
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Your TRICARE Checklist for Moving - TRICARE Newsroom (.mil)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Repairman/Lonely Wife Virgin/Experienced
11- What's your favorite restaurant? What’s your least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
4- For a pet, Cat, dog or other?
Why do narcissists avoid talking about the real issues?
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?
You know that I will be 100% truthful, so ask.
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
15- What bad habit do you wish you could quit? Do you have any addictions?
42~ What’s your biggest regret in life?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
19- Do/have you smoked? What do you prefer? How often?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
49~ How many times have you been married? Why did they end?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
9- Is there something you’ve always wanted to ask me but you’re afraid?
8- What are your thoughts on politics?
20- What’s your favorite candy? What’s your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
How many times do you think you have “made love”?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
76~ Have you had a threesome? Care to Share?
62~ Have you used adult toys?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
84~ How do you feel about reading/listening to adult stories?
18- How often do you drink alcohol? What is your favorite drink?
Over time has your thoughts on sex changed?
10- What is your favorite family tradition? What’s your least favorite?
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,
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
9~ How many times over your lifetime do you think you have had sex so far?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
What have you learned about yourself that you did not before this?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
48~ Do you have any siblings? Are you close to your family?
21~ What was the best date you ever went on? What has been the worst?
(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…)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
17- What’s your favorite holiday? What’s your least favorite?
I would allow you to do it… What would you do to me?
Can you Deep Throat? Do you like the taste of yourself?
* Give a rating for each one (0-100)
What have you learned about me that was new and/or surprising?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
13- What is the craziest/scariest thing you've ever done?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
32- What's your greatest talent? Can I see it right now?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
3- What’s your favorite smell? Do you a least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
27- What was/ is nickname? Does it have a meaning behind it?
5- Have you ever been hypnotized? Would you allow yourself to be?
How old are you? Male or Female?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Model/Photographer Police/Criminal
1- What’s your favorite animal? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
50~ How many children do you have? What are their ages?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Get this wrong and this could mean the end… :-) some funny, some not…
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Any that are a turn off?
28~ What are some things that turn on? What is your biggest turn on?
70~ Would/do you have/like anal sex?
Would you ever want to be woken up with oral and/or intercourse?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
That one or two things that made you go hmmmm, OMG or wow!
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…
Please share Did you stop?
12- What is the weirdest thing you've ever eaten?
7- What are your thoughts on religion? Is there an afterlife?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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?
*** Questions about Relationships/Past ***
10- List 5 of your top pet peeves.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
3- Should Pluto still be considered a planet? 4- How about smoking?
3- What Superhero or Superpower would you want to be/have?
2- What’s your favorite color? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Any that are a turn off?
15- What's your favorite saying? What word or phrase is your least favorite?
Prisoner/Prison Guard Landlord/Tenant
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
*** What’s Your Favorite…? ***
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
40~ What’s the weirdest place you’ve ever had sex?
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?
25~ How do you feel about PDA? (Public Display of Affection)
31- If given a chance to be immortal, would you take it? Why?
If you say it, I will stop, and we can talk about it when you are ready.
52~ What are your hobbies?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
52~ Are you willing to make “those types” of bets with your partner?
22- What is your favorite childhood memory? What is your least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
14- What is an embarrassing moment in your life? How about your most embarrassing?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If YES, was it with 2 men or 2 women? Did you enjoy it?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you watch it? What is your favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
Nothing too Serious
Escort/Client Job Applicant/Hiring Manager
The Ice Breaker Questions
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Do you like the “69” position? Do you prefer to be on top or bottom?
Have you ever? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
What is your favorite position? Why?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
18~ Who/when was your first “crush”?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Does the thought excite you? Care to share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
9- If you could have three wishes, what would they be? Why?
17- Have you ever done drugs? Which ones? How often?
11- List at least 5 things on your bucket list. Have you done any of them already?
How many partners have you had oral sex with? Who? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Master/Slave Boss/Maid
24~ What are your expectations in a relationship? (I know a very big question, take your time)
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
29~ What are some things that turn you off? What is your biggest turn 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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
11- How about if they like a certain sports team? 12-How about drinking too much?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
If you win, what will you make them do?
Will you cheat again? How can, you be sure? Define what cheating is to you.
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
15~ Have you ever been “in love”? Who? Care to Share?
47~ What would be your dream job and why?
19~ Who/when was your first “heartbreak”?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
61~ How willing would you be to try new sexual positions?
*** Questions About Me ***
38~ Share your most embarrassing sexual memory?
81~ Do you have any kinks and/or fetishes?
44~ Care to share something about yourself that no one else knows about you?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you mind if your partner watched it? How about together vs alone?
23- What is your dream job? What was it as a child?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
14- What's your favorite dessert? Do you a least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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…
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
39~ What are your love languages?
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?
*** Deal Breaker Questions ***
36~ What is your favorite time of day to have sex/make love?
7-What do I do in bed that drives you wild? How about, what turns you off?
34~ Do you like the lights on or off during sex?
51~ Are you willing to play adult games with your partner?
What do you dislike about me? I asked you to be 100% honest.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Do you think this brought you closer together?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Family Relation Age Play
22- Do you have any birth marks? How about scars? Care to share how you got them?
Do you have a favorite? Is it ok if your partner does?
48~ Have you ever paid or been paid for sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
How well do you know me? And some of your thoughts about me
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?
37- Do you like your name? If you could change it, what would you change it too?
21- What's your favorite way to spend a weekend or time off?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
83~ How do you feel about Porn?
Would you do it again, and would you rather 2 females or 2 males?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
11~ Have you ever been caught by your parents or children or others while having sex?
13~ Is there a difference between, making love, having sex, and fucking?
89~ Do you like taking showers together?
13- How about having a certain hair cut/style?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Do you like it when they show and tell you what they want?
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?
Would /have you ever given your partner a lap dance and Striptease?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
51~ What tends to bring a smile to your face?
Nurse/Patient Celebrity/Fan
If yes, what?
What would you say to prove to yourself that it was really you?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
10~ How many dates are necessary before you to have sex with someone?
8- What's your favorite flavor of ice cream? Do you a least favorite?
What is your view on sex? Meaning, When/Where/ How often/
6- Do you have dreams? Can you remember them? What do you usually dream about?
*** Random Questions ***
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
1- What was your first impression of me? Has it changed?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
30~ What's something unexpected that turns you on?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Would you read them together?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
16~ Do you believe in “soulmates”? Have you found yours? Who? 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?