What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 07:13
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
What is your favorite position? Why?
*** Random Questions ***
Costco opens a whole new kind of store - TheStreet
25~ How do you feel about PDA? (Public Display of Affection)
37- Do you like your name? If you could change it, what would you change it too?
23- What is your dream job? What was it as a child?
What have you learned about me that was new and/or surprising?
14- What's your favorite dessert? Do you a least favorite?
2- What’s your favorite color? Do you a least favorite?
Kuorans, what are some things unique to your country?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
36~ What is your favorite time of day to have sex/make love?
51~ What tends to bring a smile to your face?
What are some tips for balancing chores, work, and family life as an adult with children?
1- What’s your favorite animal? Do you a least favorite?
(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…)
You know that I will be 100% truthful, so ask.
Why are women attracted to ugly guys?
28- What are some things that people do that irritate you?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Would you read them together?
Who would win in this boxing matchup between these two, Dillian Whyte or Samuel Peter?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Get this wrong and this could mean the end… :-) some funny, some not…
Teacher/Student Stranger/One Night Stand
What are some mind-blowing facts about Michael Jackson?
9- What’s your favorite season and why? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Are Americans really as uneducated and ignorant as portrayed in the media?
48~ Have you ever paid or been paid for sex?
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 watch it? What is your favorite?
Why does a narcissist act like it's nothing when they hurt you?
Repairman/Lonely Wife Virgin/Experienced
31- If given a chance to be immortal, would you take it? Why?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Why are so many young teenage boys misogynistic? Where do they get these attitudes from?
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?
7- What’s your favorite book? Do you have a favorite genre? 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.
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Will you cheat again? How can, you be sure? Define what cheating is to you.
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
52~ Are you willing to make “those types” of bets with your partner?
If you say it, I will stop, and we can talk about it when you are ready.
*** Questions About Me ***
If YES, was it with 2 men or 2 women? Did you enjoy it?
What is your view on sex? Meaning, When/Where/ How often/
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
42~ What’s your biggest regret in life?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
62~ Have you used adult toys?
29- How superstitious are you?
Would you mind if your partner watched it? How about together vs alone?
10~ How many dates are necessary before you to have sex with someone?
Prisoner/Prison Guard Landlord/Tenant
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
19- Do/have you smoked? What do you prefer? How often?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a 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?
3- Should Pluto still be considered a planet? 4- How about smoking?
How about if they talk dirty and/or call you names?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Over time has your thoughts on sex changed?
11~ Have you ever been caught by your parents or children or others while having sex?
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…
* Give a rating for each one (0-100)
1- What was your first impression of me? Has it changed?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
The Ice Breaker Questions
Any that are a turn off?
27- What was/ is nickname? Does it have a meaning behind it?
34~ Do you like the lights on or off during sex?
If you win, what will you make them do?
What do you dislike about me? I asked you to be 100% honest.
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
38~ Share your most embarrassing sexual memory?
50~ How many children do you have? What are their ages?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
19~ Who/when was your first “heartbreak”?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
45~ How do you feel about me blindfolding you? How about blindfolding me?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
How old are you? Male or Female?
39~ What are your love languages?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Have you ever? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you like it when they show and tell you what they want?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
3- What’s your favorite smell? Do you a least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
17- What’s your favorite holiday? 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?
21~ What was the best date you ever went on? What has been the worst?
33- If you could visit any time period, when would you pick? Please explain why?
Would /have you ever given your partner a lap dance and Striptease?
89~ Do you like taking showers together?
14- What is an embarrassing moment in your life? How about your most embarrassing?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
9- Is there something you’ve always wanted to ask me but you’re afraid?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Would you do it again, and would you rather 2 females or 2 males?
15- What's your favorite saying? What word or phrase is your least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If NO, would you ever have one? Would it be with 2 men or 2 women?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
44~ Care to share something about yourself that no one else knows about 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.
*** What’s Your Favorite…? ***
11- How about if they like a certain sports team? 12-How about drinking too much?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
53~ How much can you tell me about the one thing you are most passionate about?
80~ Share your top three fantasies/desires. (Be detailed) 😊
6- Do you have dreams? Can you remember them? What do you usually dream about?
51~ Are you willing to play adult games with your partner?
5~ When you first started having sex, was it what you thought it would be?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
How many partners have you had oral sex with? Who? Care to Share?
Escort/Client Job Applicant/Hiring Manager
7-What do I do in bed that drives you wild? How about, what turns you off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
19- What’s your favorite fairytale? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
How many times do you think you have “made love”?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Would you ever want to be woken up with oral and/or intercourse?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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?
92~ Everyone needs a “safe” word. What is yours?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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?
11- What's your favorite restaurant? 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,
92~ Have you ever had or have an STD? How many? What was it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Any that are a turn off?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
*** Questions about Relationships/Past ***
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Please share Did you stop?
Master/Slave Boss/Maid
What is your favorite toy? Ever wanted to try a specific toy?
8- What are your thoughts on politics?
13- How about having a certain hair cut/style?
21- What's your favorite way to spend a weekend or time off?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
67~ Do you like it when your partner moans and/or is vocal during sex?
81~ Do you have any kinks and/or fetishes?
I would allow you to do it… What would you do to me?
What would you say to prove to yourself that it was really you?
Nurse/Patient Celebrity/Fan
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
3- What Superhero or Superpower would you want to be/have?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
If yes, what?
28~ What are some things that turn on? What is your biggest turn on?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What was the longest? What was the shortest?
9- If you could have three wishes, what would they be? Why?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
11- List at least 5 things on your bucket list. Have you done any of them already?
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…
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
61~ How willing would you be to try new sexual positions?
48~ Do you have any siblings? Are you close to your family?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
*** Deal Breaker Questions ***
30~ What's something unexpected that turns you on?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
36- Do you play video games? What is your favorite? Do you a least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
70~ Would/do you have/like anal sex?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
How well do you know me? And some of your thoughts about me
83~ How do you feel about Porn?
33- Beach or Mountains? Or is there another place to like better?
7- What if a person smells a certain way? 8- How about smoking?
13- What is the craziest/scariest thing you've ever done?
13- What’s your favorite drink? What’s your least favorite?
82~ Do you have any fantasies involving Role-Playing?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
Doctor/Nurse Stripper/Client
20- What’s your favorite candy? What’s your least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
52~ What are your hobbies?
Can you Deep Throat? Do you like the taste of yourself?
40~ What’s the weirdest place you’ve ever had sex?
15- What bad habit do you wish you could quit? Do you have any addictions?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
26~ What side of the bed do you sleep on?
13~ Is there a difference between, making love, having sex, and fucking?
71~ Would you give your partner a hand or foot job? Would you receive one?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
64~ When was your very first orgasm? When was your first from having sex? Care to share?
17- Have you ever done drugs? Which ones? How often?
10- List 5 of your top pet peeves.
18~ Who/when was your first “crush”?
34- Ever been to a concert? What was your favorite? Who would you like to see?
What have you learned about yourself that you did not before this?
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?
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)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Family Relation Age Play
Does the thought excite you? Care to share?
12- What’s your favorite food? What’s your least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you think this brought you closer together?
32- What's your greatest talent? Can I see it right now?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Model/Photographer Police/Criminal
22- What is your favorite childhood memory? What is your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
9~ How many times over your lifetime do you think you have had sex so far?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
12- What is the weirdest thing you've ever eaten?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Nothing too Serious
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
49~ How many times have you been married? Why did they end?
18- How often do you drink alcohol? What is your favorite drink?
Do you have a favorite? Is it ok if your partner does?
15~ Have you ever been “in love”? Who? Care to Share?
4- For a pet, Cat, dog or other?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?