What is the most interesting question you can ask to get to know someone?
Last Updated: 16.06.2025 02:45
12- What is the weirdest thing you've ever eaten?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Doctor/Nurse Stripper/Client
4- For a pet, Cat, dog or other?
What was the longest? What was the shortest?
What would you say to prove to yourself that it was really you?
How are you spending your best time?
92~ Everyone needs a “safe” word. What is yours?
45~ How do you feel about me blindfolding you? How about blindfolding me?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Which feels physically better for guys: vaginal sex or anal sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Get this wrong and this could mean the end… :-) some funny, some not…
7-What do I do in bed that drives you wild? How about, what turns you off?
Why do women consider 80% of men as unattractive?
9- If you could have three wishes, what would they be? Why?
1- What’s your favorite animal? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
How many partners have you had oral sex with? Who? Care to Share?
1- What was your first impression of me? Has it changed?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
What is your best forbidden sex story that felt so right?
If NO, would you ever have one? Would it be with 2 men or 2 women?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
92~ Have you ever had or have an STD? How many? What was it?
Can you name a female actress who has had bad timing or luck in her film career?
11- How about if they like a certain sports team? 12-How about drinking too much?
*** Deal Breaker Questions ***
*** Random Questions ***
Can people who have never met you tell if you are a covert narcissist?
How about if they talk dirty and/or call you names?
52~ What are your hobbies?
What have you learned about me that was new and/or surprising?
34- Ever been to a concert? What was your favorite? Who would you like to see?
18~ Who/when was your first “crush”?
Family Relation Age Play
I want to have anal sex, but my wife refuses. What do I do?
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
What is your favorite position? Why?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
34~ Do you like the lights on or off during sex?
How did Nickelback gain a large fan base despite criticism of their music?
Would you allow me to clean every part of your body with my soapy hands and fingers?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Why should the law care about what I do behind closed doors?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
81~ Do you have any kinks and/or fetishes?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
7- What if a person smells a certain way? 8- How about smoking?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Any that are a turn off?
12- What’s your favorite food? What’s your least favorite?
48~ Have you ever paid or been paid for sex?
83~ How do you feel about Porn?
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?
33- If you could visit any time period, when would you pick? Please explain why?
31- If given a chance to be immortal, would you take it? Why?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
52~ Are you willing to make “those types” of bets with your partner?
40~ What’s the weirdest place you’ve ever had sex?
10- What is your favorite family tradition? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Do you have a favorite? Is it ok if your partner does?
28- What are some things that people do that irritate you?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
30~ What's something unexpected that turns you on?
18- How often do you drink alcohol? What is your favorite drink?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
*** Questions About Me ***
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Any that are a turn off?
22- Do you have any birth marks? How about scars? Care to share how you got them?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
51~ What tends to bring a smile to your face?
15~ Have you ever been “in love”? Who? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
That one or two things that made you go hmmmm, OMG or wow!
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…
Do you shave/trim your pubic hair? For you guys do you shave your balls?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Over time has your thoughts on sex changed?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
* Give a rating for each one (0-100)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What do you dislike about me? I asked you to be 100% honest.
How many times do you think you have “made love”?
13~ Is there a difference between, making love, having sex, and fucking?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
82~ Do you have any fantasies involving Role-Playing?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
25~ How do you feel about PDA? (Public Display of Affection)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
29- How superstitious are you?
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?
42~ What’s your biggest regret in life?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
14- What is an embarrassing moment in your life? How about your most embarrassing?
9~ How many times over your lifetime do you think you have had sex so far?
13- What is the craziest/scariest thing you've ever done?
33- Beach or Mountains? Or is there another place to like better?
61~ How willing would you be to try new sexual positions?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
62~ Have you used adult toys?
If you win, what will you make them do?
44~ Care to share something about yourself that no one else knows about you?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
53~ How much can you tell me about the one thing you are most passionate about?
Would you read them together?
9- Is there something you’ve always wanted to ask me but you’re afraid?
If YES, was it with 2 men or 2 women? Did you enjoy it?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Repairman/Lonely Wife Virgin/Experienced
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
What is your view on sex? Meaning, When/Where/ How often/
11~ Have you ever been caught by your parents or children or others while having sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
5~ When you first started having sex, was it what you thought it would be?
21~ What was the best date you ever went on? What has been the worst?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
15- What bad habit do you wish you could quit? Do you have any addictions?
Teacher/Student Stranger/One Night Stand
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?
15- What's your favorite saying? What word or phrase is your least favorite?
Master/Slave Boss/Maid
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How well do you know me? And some of your thoughts about me
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Would you mind if your partner watched it? How about together vs alone?
Can you Deep Throat? Do you like the taste of yourself?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
11- What's your favorite restaurant? What’s your least favorite?
*** Questions about Relationships/Past ***
38~ Share your most embarrassing sexual memory?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Do you watch it? What is your favorite?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
29~ What are some things that turn you off? What is your biggest turn off?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Escort/Client Job Applicant/Hiring Manager
Prisoner/Prison Guard Landlord/Tenant
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
How old are you? Male or Female?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Do you think this brought you closer together?
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?
13- How about having a certain hair cut/style?
51~ Are you willing to play adult games with your partner?
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)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
36~ What is your favorite time of day to have sex/make love?
28~ What are some things that turn on? What is your biggest turn on?
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,
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Do you like it when they show and tell you what they want?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Will you cheat again? How can, you be sure? Define what cheating is to you.
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
49~ How many times have you been married? Why did they end?
26~ What side of the bed do you sleep on?
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?
Model/Photographer Police/Criminal
37- Do you like your name? If you could change it, what would you change it too?
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?
8- What are your thoughts on politics?
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
3- What’s your favorite smell? Do you a least favorite?
17- Have you ever done drugs? Which ones? How often?
You know that I will be 100% truthful, so ask.
8- What's your favorite flavor of ice cream? Do you a least favorite?
If yes, what?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
7- What are your thoughts on religion? Is there an afterlife?
70~ Would/do you have/like anal sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
2- What’s your favorite color? Do you a least favorite?
13- What’s your favorite drink? What’s your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
19~ Who/when was your first “heartbreak”?
Would /have you ever given your partner a lap dance and Striptease?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
67~ Do you like it when your partner moans and/or is vocal during sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What have you learned about yourself that you did not before this?
6- Do you have dreams? Can you remember them? What do you usually dream about?
65~ Describe the best orgasm you’ve ever had? Care to share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
39~ What are your love languages?
89~ Do you like taking showers together?
47~ What would be your dream job and why?
32- What's your greatest talent? Can I see it right now?
19- Do/have you smoked? What do you prefer? How often?
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…
21- What's your favorite way to spend a weekend or time off?
If you say it, I will stop, and we can talk about it when you are ready.
11- List at least 5 things on your bucket list. Have you done any of them already?
I would allow you to do it… What would you do to me?
76~ Have you had a threesome? Care to Share?
The Ice Breaker Questions
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Have you ever? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
10- List 5 of your top pet peeves.
84~ How do you feel about reading/listening to adult stories?
Nothing too Serious
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
71~ Would you give your partner a hand or foot job? Would you receive one?
*** What’s Your Favorite…? ***
48~ Do you have any siblings? Are you close to your family?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Does the thought excite you? Care to share?
50~ How many children do you have? What are their ages?
19- What’s your favorite fairytale? What’s your least favorite?
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?
(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…)
22- What is your favorite childhood memory? What is your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
80~ Share your top three fantasies/desires. (Be detailed) 😊
14- What's your favorite dessert? Do you a least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What is your favorite toy? Ever wanted to try a specific toy?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Please share Did you stop?
1~ How old were you when you had your first kiss? Who? Care to Share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
3- What Superhero or Superpower would you want to be/have?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
3- Should Pluto still be considered a planet? 4- How about smoking?
20- What’s your favorite candy? What’s your least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Nurse/Patient Celebrity/Fan