What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 02:42
21~ What was the best date you ever went on? What has been the worst?
44~ Care to share something about yourself that no one else knows about you?
If you say it, I will stop, and we can talk about it when you are ready.
29- How superstitious are you?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Binge Eating Disorder: Plea for specialist services in Northern Ireland - BBC
2- What’s your favorite color? Do you a least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Mariska Hargitay will reveal past secrets, new family at 'My Mom Jayne' premiere - USA Today
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
19- What’s your favorite fairytale? What’s your least favorite?
🌿🌻Why are Meghan and Harry not treated like royalty in the United States anymore?
You know that I will be 100% truthful, so ask.
How about if they talk dirty and/or call you names?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Why do women have sex with dogs?
62~ Have you used adult toys?
19~ Who/when was your first “heartbreak”?
Nothing too Serious
53~ How much can you tell me about the one thing you are most passionate about?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
83~ How do you feel about Porn?
Methane-eating sea spiders discovered off Southern California coast - SFGATE
Does the thought excite you? Care to share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What is your favorite position? Why?
Apple still has some unannounced iOS 26 features in the pipeline: report - 9to5Mac
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
Resilience spacecraft’s status after moon-landing attempt is unknown - CNN
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…
33- If you could visit any time period, when would you pick? Please explain why?
Do you like it when they show and tell you what they want?
Satellites keep breaking up in space, insurance won't cover them. - Space
Please share Did you stop?
89~ Do you like taking showers together?
15~ Have you ever been “in love”? Who? Care to Share?
Milky Way has 50-50 chance of colliding with neighbor galaxy - NewsNation
Would you mind if your partner watched it? How about together vs alone?
Would /have you ever given your partner a lap dance and Striptease?
10~ How many dates are necessary before you to have sex with someone?
Will you cheat again? How can, you be sure? Define what cheating is to you.
* Give a rating for each one (0-100)
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?
As Cannabis Users Age, Health Risks Appear To Grow - KFF Health News
What is your favorite toy? Ever wanted to try a specific toy?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
Anycubic has yet another sale happening, and the 3D printer I own is $200 off - Creative Bloq
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?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
70~ Would/do you have/like anal sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Repairman/Lonely Wife Virgin/Experienced
If YES, was it with 2 men or 2 women? Did you enjoy it?
7- What are your thoughts on religion? Is there an afterlife?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Any that are a turn off?
What have you learned about me that was new and/or surprising?
What do you dislike about me? I asked you to be 100% honest.
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
48~ Do you have any siblings? Are you close to your family?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
30~ What's something unexpected that turns you on?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If yes, what?
29~ What are some things that turn you off? What is your biggest turn off?
3- Should Pluto still be considered a planet? 4- How about smoking?
38~ Share your most embarrassing sexual memory?
52~ What are your hobbies?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Do you think this brought you closer together?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Would you ever want to be woken up with oral and/or intercourse?
1- What’s your favorite animal? Do you a least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
12- What’s your favorite food? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
9- Is there something you’ve always wanted to ask me but you’re afraid?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
42~ What’s your biggest regret in life?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
15- What's your favorite saying? What word or phrase is your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
5- Have you ever been hypnotized? Would you allow yourself to be?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How old are you? Male or Female?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
80~ Share your top three fantasies/desires. (Be detailed) 😊
46~ Have you ever used furniture, or other types of things to aid you while having sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
37- Do you like your name? If you could change it, what would you change it too?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What would you say to prove to yourself that it was really you?
28~ What are some things that turn on? What is your biggest turn on?
34~ Do you like the lights on or off during sex?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
61~ How willing would you be to try new sexual positions?
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
21- What's your favorite way to spend a weekend or time off?
*** Random Questions ***
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
The Ice Breaker Questions
92~ Have you ever had or have an STD? How many? What was it?
*** What’s Your Favorite…? ***
If NO, would you ever have one? Would it be with 2 men or 2 women?
*** Questions about Relationships/Past ***
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Over time has your thoughts on sex changed?
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?
8- What are your thoughts on politics?
92~ Everyone needs a “safe” word. What is yours?
How many times do you think you have “made love”?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
36- Do you play video games? What is your favorite? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
11~ Have you ever been caught by your parents or children or others while having sex?
I would allow you to do it… What would you do to me?
84~ How do you feel about reading/listening to adult stories?
How many partners have you had oral sex with? Who? Care to Share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
7- What if a person smells a certain way? 8- How about smoking?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
3- What’s your favorite smell? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
18- How often do you drink alcohol? What is your favorite drink?
19- Do/have you smoked? What do you prefer? How often?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
Do you have a favorite? Is it ok if your partner does?
What have you learned about yourself that you did not before this?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
1~ How old were you when you had your first kiss? Who? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
12- What is the weirdest thing you've ever eaten?
Family Relation Age Play
51~ What tends to bring a smile to your face?
How well do you know me? And some of your thoughts about me
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
13- What is the craziest/scariest thing you've ever done?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
18~ Who/when was your first “crush”?
4- For a pet, Cat, dog or other?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
81~ Do you have any kinks and/or fetishes?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
6- Do you have dreams? Can you remember them? What do you usually dream about?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
*** Deal Breaker Questions ***
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
13- How about having a certain hair cut/style?
Do you watch it? What is your favorite?
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
25~ How do you feel about PDA? (Public Display of Affection)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Have you ever? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Would you do it again, and would you rather 2 females or 2 males?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Model/Photographer Police/Criminal
What was the longest? What was the shortest?
Prisoner/Prison Guard Landlord/Tenant
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…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
82~ Do you have any fantasies involving Role-Playing?
11- List at least 5 things on your bucket list. Have you done any of them already?
47~ What would be your dream job and why?
(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…)
13~ Is there a difference between, making love, having sex, and fucking?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
15- What bad habit do you wish you could quit? Do you have any addictions?
What is your view on sex? Meaning, When/Where/ How often/
13- What’s your favorite drink? What’s your least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Escort/Client Job Applicant/Hiring Manager
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
22- What is your favorite childhood memory? What is your least favorite?
39~ What are your love languages?
10- List 5 of your top pet peeves.
31- If given a chance to be immortal, would you take it? Why?
Would you read them together?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Master/Slave Boss/Maid
8- What's your favorite flavor of ice cream? Do you a least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
17- Have you ever done drugs? Which ones? How often?
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,
28- What are some things that people do that irritate you?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
*** Questions About 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?
3- What Superhero or Superpower would you want to be/have?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Any that are a turn off?
48~ Have you ever paid or been paid for sex?
That one or two things that made you go hmmmm, OMG or wow!
23- What is your dream job? What was it as a child?
51~ Are you willing to play adult games with your partner?
9- If you could have three wishes, what would they be? Why?
Doctor/Nurse Stripper/Client
49~ How many times have you been married? Why did they end?
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
40~ What’s the weirdest place you’ve ever had sex?
50~ How many children do you have? What are their ages?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
1- What was your first impression of me? Has it changed?
Nurse/Patient Celebrity/Fan
22- Do you have any birth marks? How about scars? Care to share how you got them?
Do you like the “69” position? Do you prefer to be on top or bottom?
26~ What side of the bed do you sleep on?
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?
5~ When you first started having sex, was it what you thought it would be?
76~ Have you had a threesome? Care to Share?
32- What's your greatest talent? Can I see it right now?
7-What do I do in bed that drives you wild? How about, what turns you off?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
14- What's your favorite dessert? Do you a least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
11- What's your favorite restaurant? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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)
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?
If you win, what will you make them do?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
52~ Are you willing to make “those types” of bets with your partner?