What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 00:55

80~ Share your top three fantasies/desires. (Be detailed) đ
Can you Deep Throat? Do you like the taste of yourself?
22- Do you have any birth marks? How about scars? Care to share how you got them?
What are the 10 things you regret doing in your life?
23- What is your dream job? What was it as a child?
What is your favorite toy? Ever wanted to try a specific toy?
Would you do it again, and would you rather 2 females or 2 males?
What is your worst experience in life?
48~ Have you ever paid or been paid for sex?
Take the short quiz here @ Discover Your Love LanguageÂź - The 5 Love LanguagesÂź
9~ How many times over your lifetime do you think you have had sex so far?
25~ How do you feel about PDA? (Public Display of Affection)
Do you watch it? What is your favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
15~ Have you ever been âin loveâ? Who? Care to Share?
Do you like it when they show and tell you what they want?
34~ Do you like the lights on or off during sex?
Do you have a favorite? Is it ok if your partner does?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What is a narcissist grandmother like, with her grandchild?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
11- What's your favorite restaurant? Whatâs your least favorite?
* Give a rating for each one (0-100)
Why won't my mom let me come home if I'm homeless?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
17- Whatâs your favorite holiday? Whatâs your least favorite?
9- Whatâs your favorite season and why? Whatâs your least favorite?
*** Random Questions ***
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
39~ What are your love languages?
42~ Whatâs your biggest regret in life?
21- What's your favorite way to spend a weekend or time off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
62~ Have you used adult toys?
76~ Have you had a threesome? Care to Share?
Stock futures fall as investors eye Israel-Iran conflict: Live updates - CNBC
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Have you ever? Care to Share?
Would you mind if your partner watched it? How about together vs alone?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŠ
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
If you get a chance to have sex with either Kajal Agarwal or Samantha, who would you choose and why?
How well do you know me? And some of your thoughts about me
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)
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
What do you do when your family doesnât care about you?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couplesâ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETCâŠ)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Whatâs the saddest thing youâve seen at your job?
Over time has your thoughts on sex changed?
33- Beach or Mountains? Or is there another place to like better?
If you win, what will you make them do?
12- Whatâs your favorite food? Whatâs your least favorite?
The Ice Breaker Questions
1- What was your first impression of me? Has it changed?
What is your view on sex? Meaning, When/Where/ How often/
Master/Slave Boss/Maid
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
81~ Do you have any kinks and/or fetishes?
50~ How many children do you have? What are their ages?
7- What if a person smells a certain way? 8- How about smoking?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
How about if they talk dirty and/or call you names?
26~ What side of the bed do you sleep on?
Get this wrong and this could mean the end⊠:-) some funny, some notâŠ
Doctor/Nurse Stripper/Client
13- Whatâs your favorite drink? Whatâs your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
21~ What was the best date you ever went on? What has been the worst?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
37- Do you like your name? If you could change it, what would you change it too?
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?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
7-What do I do in bed that drives you wild? How about, what turns you off?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
33- If you could visit any time period, when would you pick? Please explain why?
8- What are your thoughts on politics?
82~ Do you have any fantasies involving Role-Playing?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
8- What's your favorite flavor of ice cream? Do you a least favorite?
84~ How do you feel about reading/listening to adult stories?
7- What are your thoughts on religion? Is there an afterlife?
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
52~ Are you willing to make âthose typesâ of bets with your partner?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Any that are a turn off?
60~ How important is oral sex? Do you like receiving? Do you like giving?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
I would allow you to do it⊠What would you do to me?
Family Relation Age Play
4- For a pet, Cat, dog or other?
*** Questions about Relationships/Past ***
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!
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
What would you say to prove to yourself that it was really you?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Piecing, tattoo, color hair, dress up a certain way, it could be anything⊠Shave meâŠ
Do you think this brought you closer together?
Prisoner/Prison Guard Landlord/Tenant
3- Should Pluto still be considered a planet? 4- How about smoking?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Does the thought excite you? Care to share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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 you read them together?
36~ What is your favorite time of day to have sex/make love?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
12- What is the weirdest thing you've ever eaten?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
If YES, was it with 2 men or 2 women? Did you enjoy it?
11- How about if they like a certain sports team? 12-How about drinking too much?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Will you cheat again? How can, you be sure? Define what cheating is to you.
Model/Photographer Police/Criminal
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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?
1~ How old were you when you had your first kiss? Who? Care to Share?
51~ Are you willing to play adult games with your partner?
Nurse/Patient Celebrity/Fan
27- What was/ is nickname? Does it have a meaning behind it?
10- What is your favorite family tradition? Whatâs your least 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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
11- List at least 5 things on your bucket list. Have you done any of them already?
18~ Who/when was your first âcrushâ?
20- Whatâs your favorite candy? Whatâs your least favorite?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
31- If given a chance to be immortal, would you take it? Why?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŠ
10- List 5 of your top pet peeves.
Do you like the â69â position? Do you prefer to be on top or bottom?
61~ How willing would you be to try new sexual positions?
*** Whatâs Your FavoriteâŠ? ***
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
13~ Is there a difference between, making love, having sex, and fucking?
You know that I will be 100% truthful, so ask.
29- How superstitious are you?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
38~ Share your most embarrassing sexual memory?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
49~ How many times have you been married? Why did they end?
30~ What's something unexpected that turns you on?
If you say it, I will stop, and we can talk about it when you are ready.
85~ If I gave you a âFree Passâ for you to do anything to me for one hour, knowing that no matter what you did,
51~ What tends to bring a smile to your face?
If NO, would you ever have one? Would it be with 2 men or 2 women?
14- Do you have a âDeal Breakerâ, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
22- What is your favorite childhood memory? What is your least favorite?
19~ Who/when was your first âheartbreakâ?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
19- Do/have you smoked? What do you prefer? How often?
36- Do you play video games? What is your favorite? Do you a least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Would you allow me to clean every part of your body with my soapy hands and fingers?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
17- Have you ever done drugs? Which ones? How often?
2- Whatâs your favorite color? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
70~ Would/do you have/like anal sex?
9- Is there something youâve always wanted to ask me but youâre afraid?
34- Ever been to a concert? What was your favorite? Who would you like to see?
92~ Everyone needs a âsafeâ word. What is yours?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
44~ Care to share something about yourself that no one else knows about you?
13- What is the craziest/scariest thing you've ever done?
If yes, what?
*** Deal Breaker Questions ***
Repairman/Lonely Wife Virgin/Experienced
5- Have you ever been hypnotized? Would you allow yourself to be?
9- If you could have three wishes, what would they be? Why?
65~ Describe the best orgasm youâve ever had? Care to share?
1- Whatâs your favorite animal? Do you a least favorite?
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
48~ Do you have any siblings? Are you close to your family?
32- What's your greatest talent? Can I see it right now?
3- What was the most surprising thing youâve learned about me throughout our relationship?
What was the longest? What was the shortest?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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 togetherâŠ
92~ Have you ever had or have an STD? How many? What was it?
28~ What are some things that turn on? What is your biggest turn on?
3- Whatâs your favorite smell? Do you a 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?
How old are you? Male or Female?
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
*** Questions About Me ***
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
What have you learned about me that was new and/or surprising?
71~ Would you give your partner a hand or foot job? Would you receive one?
40~ Whatâs the weirdest place youâve ever had sex?
How many partners have you had oral sex with? Who? Care to Share?
What is your favorite position? Why?
52~ What are your hobbies?
5~ When you first started having sex, was it what you thought it would be?
14- What's your favorite dessert? Do you a least favorite?
83~ How do you feel about Porn?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
85~ If you gave me a âfree Passâ to have me do anything for one hour, what would you want me to do to you?
89~ Do you like taking showers together?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Teacher/Student Stranger/One Night Stand
15- What bad habit do you wish you could quit? Do you have any addictions?
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, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
13- How about having a certain hair cut/style?
28- What are some things that people do that irritate you?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
29~ What are some things that turn you off? What is your biggest turn off?
Escort/Client Job Applicant/Hiring Manager
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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?
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
3- What Superhero or Superpower would you want to be/have?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Any that are a turn off?
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 âPASSâ 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 yourselfâŠ
11~ Have you ever been caught by your parents or children or others while having sex?
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Please share Did you stop?
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
What have you learned about yourself that you did not before this?
Would /have you ever given your partner a lap dance and Striptease?
19- Whatâs your favorite fairytale? Whatâs your least favorite?
10~ How many dates are necessary before you to have sex with someone?
47~ What would be your dream job and why?
14 â Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
18- How often do you drink alcohol? What is your favorite drink?
How many times do you think you have âmade loveâ?
Nothing too Serious