What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 11:51
15- What bad habit do you wish you could quit? Do you have any addictions?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
71~ Would you give your partner a hand or foot job? Would you receive one?
51~ Are you willing to play adult games with your partner?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
50~ How many children do you have? What are their ages?
Why are Republican politicians so afraid to oppose Trump?
How many times do you think you have “made love”?
29- How superstitious are you?
20- What’s your favorite candy? What’s your least favorite?
How short is too short for a skirt?
83~ How do you feel about Porn?
If yes, what?
92~ Have you ever had or have an STD? How many? What was it?
Why do some women squirt and some don't?
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?
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?
*** Random Questions ***
I'm pretty sure that my dog is transgender, how would I go about transitioning it?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
47~ What would be your dream job and why?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
*** Questions about Relationships/Past ***
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
9- If you could have three wishes, what would they be? Why?
Has your wife or girlfriend ever been felt up in public by a stranger?
What would you say to prove to yourself that it was really you?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
80~ Share your top three fantasies/desires. (Be detailed) 😊
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Prisoner/Prison Guard Landlord/Tenant
What’s the longest time you gone without having sex, after, having it? How much time between the others?
22- What is your favorite childhood memory? What is your least favorite?
1- What was your first impression of me? Has it changed?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Why are white women so overly emotional?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
Have you ever? Care to Share?
Why do narcissist move on so easily?
11- List at least 5 things on your bucket list. Have you done any of them already?
If NO, would you ever have one? Would it be with 2 men or 2 women?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Can you share something that captivates you, whether it's an idea, a discovery, or an invention?
40~ What’s the weirdest place you’ve ever had sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
‘Gas station heroin’ is technically illegal and widely available. Here are the facts - WANE 15
34~ Do you like the lights on or off during sex?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
That one or two things that made you go hmmmm, OMG or wow!
* Give a rating for each one (0-100)
Do you think this brought you closer together?
Would you mind if your partner watched it? How about together vs alone?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
4- For a pet, Cat, dog or other?
76~ Have you had a threesome? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
18~ Who/when was your first “crush”?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
19- What’s your favorite fairytale? What’s your least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
39~ What are your love languages?
Would you do it again, and would you rather 2 females or 2 males?
How about if they talk dirty and/or call you names?
Family Relation Age Play
7-What do I do in bed that drives you wild? How about, what turns you off?
Over time has your thoughts on sex changed?
Nothing too Serious
If YES, was it with 2 men or 2 women? Did you enjoy it?
12- What is the weirdest thing you've ever eaten?
17- What’s your favorite holiday? What’s your least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would you ever want to be woken up with oral and/or intercourse?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Would you read them together?
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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Do you have a favorite? Is it ok if your partner does?
5- Have you ever been hypnotized? Would you allow yourself to be?
18- How often do you drink alcohol? What is your favorite drink?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Any that are a turn off?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
48~ Have you ever paid or been paid for sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
10~ How many dates are necessary before you to have sex with someone?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
37- Do you like your name? If you could change it, what would you change it too?
Will you cheat again? How can, you be sure? Define what cheating is to you.
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
28- What are some things that people do that irritate you?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
Repairman/Lonely Wife Virgin/Experienced
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
5~ When you first started having sex, was it what you thought it would be?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
10- What is your favorite family tradition? What’s your least favorite?
1- What’s your favorite animal? Do you a least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
3- What Superhero or Superpower would you want to be/have?
23- What is your dream job? What was it as a child?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
45~ How do you feel about me blindfolding you? How about blindfolding me?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Doctor/Nurse Stripper/Client
Do you like the “69” position? Do you prefer to be on top or bottom?
84~ How do you feel about reading/listening to adult stories?
22- Do you have any birth marks? How about scars? Care to share how you got them?
8- What's your favorite flavor of ice cream? Do you a least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
9- What’s your favorite season and why? What’s your least favorite?
Model/Photographer Police/Criminal
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
19~ Who/when was your first “heartbreak”?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
7- What are your thoughts on religion? Is there an afterlife?
2- What’s your favorite color? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
33- Beach or Mountains? Or is there another place to like better?
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…
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What was the longest? What was the shortest?
13- What’s your favorite drink? What’s your least favorite?
What is your favorite position? Why?
51~ What tends to bring a smile to your face?
92~ Everyone needs a “safe” word. What is yours?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
82~ Do you have any fantasies involving Role-Playing?
What is your favorite toy? Ever wanted to try a specific toy?
38~ Share your most embarrassing sexual memory?
What have you learned about yourself that you did not before this?
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
11- What's your favorite restaurant? What’s your least favorite?
32- What's your greatest talent? Can I see it right now?
53~ How much can you tell me about the one thing you are most passionate about?
28~ What are some things that turn on? What is your biggest turn on?
Nurse/Patient Celebrity/Fan
14- What's your favorite dessert? Do you a least favorite?
12- What’s your favorite food? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
27- What was/ is nickname? Does it have a meaning behind it?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
(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…)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
8- What are your thoughts on politics?
1~ How old were you when you had your first kiss? Who? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How many partners have you had oral sex with? Who? Care to Share?
How well do you know me? And some of your thoughts about me
Do you watch it? What is your favorite?
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?
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?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
I would allow you to do it… What would you do to me?
7- What if a person smells a certain way? 8- How about smoking?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
65~ Describe the best orgasm you’ve ever had? Care to share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
You know that I will be 100% truthful, so ask.
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…
Can you Deep Throat? Do you like the taste of yourself?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What is your view on sex? Meaning, When/Where/ How often/
48~ Do you have any siblings? Are you close to your family?
Would you allow me to clean every part of your body with my soapy hands and fingers?
31- If given a chance to be immortal, would you take it? Why?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
62~ Have you used adult toys?
70~ Would/do you have/like anal sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Master/Slave Boss/Maid
60~ How important is oral sex? Do you like receiving? Do you like giving?
61~ How willing would you be to try new sexual positions?
Please share Did you stop?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
9~ How many times over your lifetime do you think you have had sex so far?
What do you dislike about me? I asked you to be 100% honest.
30~ What's something unexpected that turns you on?
3- What’s your favorite smell? Do you a least favorite?
42~ What’s your biggest regret in life?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
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,
3- What was the most surprising thing you’ve learned about me throughout our relationship?
25~ How do you feel about PDA? (Public Display of Affection)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Do you like it when they show and tell you what they want?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
67~ Do you like it when your partner moans and/or is vocal during sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
What have you learned about me that was new and/or surprising?
Escort/Client Job Applicant/Hiring Manager
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
89~ Do you like taking showers together?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
The Ice Breaker Questions
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
49~ How many times have you been married? Why did they end?
Get this wrong and this could mean the end… :-) some funny, some not…
52~ What are your hobbies?
17- Have you ever done drugs? Which ones? How often?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
If you say it, I will stop, and we can talk about it when you are ready.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
21~ What was the best date you ever went on? What has been the worst?
Does the thought excite you? Care to share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
3- Should Pluto still be considered a planet? 4- How about smoking?
81~ Do you have any kinks and/or fetishes?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
36~ What is your favorite time of day to have sex/make love?
13~ Is there a difference between, making love, having sex, and fucking?
Any that are a turn off?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Teacher/Student Stranger/One Night Stand
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
If you win, what will you make them do?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Would /have you ever given your partner a lap dance and Striptease?
*** What’s Your Favorite…? ***
13- What is the craziest/scariest thing you've ever done?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
10- List 5 of your top pet peeves.
44~ Care to share something about yourself that no one else knows about you?
13- How about having a certain hair cut/style?
*** Questions About Me ***
How old are you? Male or Female?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
33- If you could visit any time period, when would you pick? Please explain why?
*** Deal Breaker Questions ***
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
15- What's your favorite saying? What word or phrase is your least favorite?
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)
11- How about if they like a certain sports team? 12-How about drinking too much?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
15~ Have you ever been “in love”? Who? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
29~ What are some things that turn you off? What is your biggest turn off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?