What is the most interesting question you can ask to get to know someone?
Last Updated: 27.06.2025 23:56
52~ Are you willing to make “those types” of bets with your partner?
18- How often do you drink alcohol? What is your favorite drink?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
How about if they talk dirty and/or call you names?
Do you think this brought you closer together?
8- What's your favorite flavor of ice cream? Do you a least favorite?
BlackRock removed from Texas blacklist after climate policy rollback - Financial Times
(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…)
19- What’s your favorite fairytale? What’s your least favorite?
I would allow you to do it… What would you do to me?
Elly De La Cruz throws out Javier Baez with mind-boggling 98 mph throw - New York Post
25~ How do you feel about PDA? (Public Display of Affection)
22- Do you have any birth marks? How about scars? Care to share how you got them?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
36~ What is your favorite time of day to have sex/make love?
Have you ever? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
Knicks-Pacers: 5 takeaways as Indiana eliminates New York, advances to 2025 Finals - NBA
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
Flipping two atoms in LSD turned it into a powerful treatment for damaged brain circuits - PsyPost
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
If yes, what?
Which services sell most on Fiverr?
13- What is the craziest/scariest thing you've ever done?
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?
NBA Draft will have tons of international talent, which is to be expected - NBA
17- Have you ever done drugs? Which ones? How often?
3- Should Pluto still be considered a planet? 4- How about smoking?
71~ Would you give your partner a hand or foot job? Would you receive one?
Speech by Governor Kugler on the economic outlook and monetary policy - Federal Reserve Board (.gov)
12- What’s your favorite food? What’s your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
89~ Do you like taking showers together?
Laudantium rerum sunt ipsa minima corporis exercitationem cupiditate.
Model/Photographer Police/Criminal
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Major supermarket chain workers start strike across 4 cities - TheStreet
Any that are a turn off?
83~ How do you feel about Porn?
9~ How many times over your lifetime do you think you have had sex so far?
92~ Have you ever had or have an STD? How many? What was it?
9- If you could have three wishes, what would they be? Why?
33- Beach or Mountains? Or is there another place to like better?
Who are the most underrated and under-appreciated Hollywood actors/actresses?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What would you say to prove to yourself that it was really you?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
62~ Have you used adult toys?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
60~ How important is oral sex? Do you like receiving? Do you like giving?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
What have you learned about me that was new and/or surprising?
Does the thought excite you? Care to share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
If YES, was it with 2 men or 2 women? Did you enjoy it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Please share Did you stop?
Over time has your thoughts on sex changed?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How many times do you think you have “made love”?
13- What’s your favorite drink? What’s your least favorite?
26~ What side of the bed do you sleep on?
4- For a pet, Cat, dog or other?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Do you like it when they show and tell you what they want?
If NO, would you ever have one? Would it be with 2 men or 2 women?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
33- If you could visit any time period, when would you pick? Please explain why?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
11- List at least 5 things on your bucket list. Have you done any of them already?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
47~ What would be your dream job and why?
22- What is your favorite childhood memory? What is your least favorite?
*** What’s Your Favorite…? ***
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
29- How superstitious are you?
49~ How many times have you been married? Why did they end?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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…
*** Questions about Relationships/Past ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
*** Deal Breaker Questions ***
Would you mind if your partner watched it? How about together vs alone?
Prisoner/Prison Guard Landlord/Tenant
5~ When you first started having sex, was it what you thought it would be?
13~ Is there a difference between, making love, having sex, and fucking?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What do you dislike about me? I asked you to be 100% honest.
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Doctor/Nurse Stripper/Client
21- What's your favorite way to spend a weekend or time off?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
50~ How many children do you have? What are their ages?
10- List 5 of your top pet peeves.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
8- What are your thoughts on politics?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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?
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,
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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?
9- What’s your favorite season and why? What’s your least favorite?
1- What’s your favorite animal? Do you a least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Do you like the “69” position? Do you prefer to be on top or bottom?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
81~ Do you have any kinks and/or fetishes?
51~ What tends to bring a smile to your face?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
2- What’s your favorite color? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
53~ How much can you tell me about the one thing you are most passionate about?
Do you watch it? What is your favorite?
How well do you know me? And some of your thoughts about me
48~ Do you have any siblings? Are you close to your family?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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)
Can you Deep Throat? Do you like the taste of yourself?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
The Ice Breaker Questions
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
15~ Have you ever been “in love”? Who? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
27- What was/ is nickname? Does it have a meaning behind it?
What is your favorite position? Why?
Get this wrong and this could mean the end… :-) some funny, some not…
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Nurse/Patient Celebrity/Fan
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
42~ What’s your biggest regret in life?
Any that are a turn off?
48~ Have you ever paid or been paid for sex?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Would you do it again, and would you rather 2 females or 2 males?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
84~ How do you feel about reading/listening to adult stories?
Master/Slave Boss/Maid
70~ Would/do you have/like anal sex?
18~ Who/when was your first “crush”?
32- What's your greatest talent? Can I see it right now?
How old are you? Male or Female?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
What is your view on sex? Meaning, When/Where/ How often/
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…
19~ Who/when was your first “heartbreak”?
76~ Have you had a threesome? Care to Share?
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…
15- What bad habit do you wish you could quit? Do you have any addictions?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Do you have a favorite? Is it ok if your partner does?
13- How about having a certain hair cut/style?
37- Do you like your name? If you could change it, what would you change it too?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
51~ Are you willing to play adult games with your partner?
10~ How many dates are necessary before you to have sex with someone?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
21~ What was the best date you ever went on? What has been the worst?
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?
11- How about if they like a certain sports team? 12-How about drinking too much?
10- What is your favorite family tradition? What’s your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
If you win, what will you make them do?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
*** Questions About Me ***
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
40~ What’s the weirdest place you’ve ever had sex?
Family Relation Age Play
7-What do I do in bed that drives you wild? How about, what turns you off?
3- What Superhero or Superpower would you want to be/have?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
How many partners have you had oral sex with? Who? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
6- Do you have dreams? Can you remember them? What do you usually dream about?
28~ What are some things that turn on? What is your biggest turn on?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Would /have you ever given your partner a lap dance and Striptease?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
You know that I will be 100% truthful, so ask.
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
34- Ever been to a concert? What was your favorite? Who would you like to see?
11~ Have you ever been caught by your parents or children or others while having sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What have you learned about yourself that you did not before this?
If you say it, I will stop, and we can talk about it when you are ready.
15- What's your favorite saying? What word or phrase is your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
3- What’s your favorite smell? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
*** Random Questions ***
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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?
44~ Care to share something about yourself that no one else knows about you?
* Give a rating for each one (0-100)
7- What if a person smells a certain way? 8- How about smoking?
Would you allow me to clean every part of your body with my soapy hands and fingers?
28- What are some things that people do that irritate you?
45~ How do you feel about me blindfolding you? How about blindfolding me?
31- If given a chance to be immortal, would you take it? Why?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
7- What are your thoughts on religion? Is there an afterlife?
19- Do/have you smoked? What do you prefer? How often?
12- What is the weirdest thing you've ever eaten?
39~ What are your love languages?
1~ How old were you when you had your first kiss? Who? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
52~ What are your hobbies?
30~ What's something unexpected that turns you 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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
38~ Share your most embarrassing sexual memory?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
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~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
What was the longest? What was the shortest?
5- Have you ever been hypnotized? Would you allow yourself to be?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
That one or two things that made you go hmmmm, OMG or wow!
9- Is there something you’ve always wanted to ask me but you’re afraid?
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)
29~ What are some things that turn you off? What is your biggest turn off?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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?
20- What’s your favorite candy? What’s your least favorite?
Would you read them together?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Teacher/Student Stranger/One Night Stand
92~ Everyone needs a “safe” word. What is yours?
Escort/Client Job Applicant/Hiring Manager
61~ How willing would you be to try new sexual positions?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
80~ Share your top three fantasies/desires. (Be detailed) 😊
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Nothing too Serious
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
36- Do you play video games? What is your favorite? Do you a least favorite?
34~ Do you like the lights on or off during sex?