What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 05:27
*** Questions About Me ***
The Ice Breaker Questions
33- If you could visit any time period, when would you pick? Please explain why?
Nutritionists Rank The Best (And Worst) Packaged Deli Meats For Your Health - HuffPost
31- If given a chance to be immortal, would you take it? Why?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
How many partners have you had oral sex with? Who? Care to Share?
What's wrong with white women?
3- What’s your favorite smell? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Would you read them together?
26~ What side of the bed do you sleep on?
(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…)
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
What's the biggest myth about illegal immigrants?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
83~ How do you feel about Porn?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
I am glad you enjoyed my pictures. Do you have any photos to share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
How about if they talk dirty and/or call you names?
You know that I will be 100% truthful, so ask.
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?
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Over time has your thoughts on sex changed?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
When do you start "growing old"?
Model/Photographer Police/Criminal
44~ Care to share something about yourself that no one else knows about you?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
After 70 years of the crappiest computers ever made, why does IBM exist?
Repairman/Lonely Wife Virgin/Experienced
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
36~ What is your favorite time of day to have sex/make love?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
70~ Would/do you have/like anal sex?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
How do I identify fake friends in life?
13- What’s your favorite drink? What’s your least favorite?
17- Have you ever done drugs? Which ones? How often?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Jonas Brothers cancel and move upcoming concerts, including one in North Texas - WFAA
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
30~ What's something unexpected that turns you on?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Is it just me, or do we all hate Sasuke from Naruto?
Do you think this brought you closer together?
32- What's your greatest talent? Can I see it right now?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
36- Do you play video games? What is your favorite? Do you a least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
14- What's your favorite dessert? Do you a least favorite?
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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
25~ How do you feel about PDA? (Public Display of Affection)
53~ How much can you tell me about the one thing you are most passionate about?
84~ How do you feel about reading/listening to adult stories?
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
*** Deal Breaker Questions ***
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
89~ Do you like taking showers together?
4- For a pet, Cat, dog or other?
18~ Who/when was your first “crush”?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
3- What Superhero or Superpower would you want to be/have?
*** Questions about Relationships/Past ***
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
*** Random Questions ***
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
92~ Everyone needs a “safe” word. What is yours?
11- What's your favorite restaurant? What’s your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
Can you Deep Throat? Do you like the taste of yourself?
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?
17- What’s your favorite holiday? What’s your least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
13- How about having a certain hair cut/style?
15~ Have you ever been “in love”? Who? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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?
12- What is the weirdest thing you've ever eaten?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7- What if a person smells a certain way? 8- How about smoking?
What is your favorite position? Why?
39~ What are your love languages?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
21- What's your favorite way to spend a weekend or time off?
61~ How willing would you be to try new sexual positions?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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 prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
42~ What’s your biggest regret in life?
Have you ever? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Would you allow me to clean every part of your body with my soapy hands and fingers?
71~ Would you give your partner a hand or foot job? Would you receive one?
Do you like it when they show and tell you what they want?
28- What are some things that people do that irritate you?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Escort/Client Job Applicant/Hiring Manager
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Teacher/Student Stranger/One Night Stand
47~ What would be your dream job and why?
65~ Describe the best orgasm you’ve ever had? Care to share?
12- What’s your favorite food? What’s your least favorite?
Any that are a turn off?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
That one or two things that made you go hmmmm, OMG or wow!
Prisoner/Prison Guard Landlord/Tenant
92~ Have you ever had or have an STD? How many? What was it?
40~ What’s the weirdest place you’ve ever had sex?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
How many times do you think you have “made love”?
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- What was the most surprising thing you’ve learned about me throughout our relationship?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Please share Did you stop?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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…
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
8- What's your favorite flavor of ice cream? Do you a least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
1- What was your first impression of me? Has it changed?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Master/Slave Boss/Maid
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Doctor/Nurse Stripper/Client
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Will you cheat again? How can, you be sure? Define what cheating is to you.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
9~ How many times over your lifetime do you think you have had sex so far?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
10~ How many dates are necessary before you to have sex with someone?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
20- Do you have any tattoos? 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?
76~ Have you had a threesome? Care to Share?
29- How superstitious are you?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3- Should Pluto still be considered a planet? 4- How about smoking?
20- What’s your favorite candy? What’s your least favorite?
21~ What was the best date you ever went on? What has been the worst?
Do you like the “69” position? Do you prefer to be on top or bottom?
48~ Do you have any siblings? Are you close to your family?
How old are you? Male or Female?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
15- What's your favorite saying? What word or phrase is your least favorite?
Would /have you ever given your partner a lap dance and Striptease?
48~ Have you ever paid or been paid for sex?
What have you learned about yourself that you did not before this?
* Give a rating for each one (0-100)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
82~ Do you have any fantasies involving Role-Playing?
22- Do you have any birth marks? How about scars? Care to share how you got them?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
37- Do you like your name? If you could change it, what would you change it too?
29~ What are some things that turn you off? What is your biggest turn off?
38~ Share your most embarrassing sexual memory?
What have you learned about me that was new and/or surprising?
If yes, what?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
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?
52~ Are you willing to make “those types” of bets with your partner?
13~ Is there a difference between, making love, having sex, and fucking?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Would you do it again, and would you rather 2 females or 2 males?
33- Beach or Mountains? Or is there another place to like better?
1~ How old were you when you had your first kiss? Who? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
19- Do/have you smoked? What do you prefer? How often?
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…? ***
9- What’s your favorite season and why? What’s your least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
23- What is your dream job? What was it as a child?
What would you say to prove to yourself that it was really you?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
51~ What tends to bring a smile to your face?
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Does the thought excite you? Care to share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
8- What are your thoughts on politics?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Would you ever want to be woken up with oral and/or intercourse?
18- How often do you drink alcohol? What is your favorite drink?
10- What is your favorite family tradition? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
62~ Have you used adult toys?
How well do you know me? And some of your thoughts about me
Family Relation Age Play
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
2- What’s your favorite color? Do you a least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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,
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
49~ How many times have you been married? Why did they end?
81~ Do you have any kinks and/or fetishes?
51~ Are you willing to play adult games with your partner?
45~ How do you feel about me blindfolding you? How about blindfolding me?
7-What do I do in bed that drives you wild? How about, what turns you off?
7- What are your thoughts on religion? Is there an afterlife?
Would you mind if your partner watched it? How about together vs alone?
If NO, would you ever have one? Would it be with 2 men or 2 women?
What is your view on sex? Meaning, When/Where/ How often/
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Any that are a turn off?
Nothing too Serious
I would allow you to do it… What would you do to me?
If YES, was it with 2 men or 2 women? Did you enjoy it?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you have a favorite? Is it ok if your partner does?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Nurse/Patient Celebrity/Fan
9- Is there something you’ve always wanted to ask me but you’re afraid?
11- How about if they like a certain sports team? 12-How about drinking too much?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
52~ What are your hobbies?
What do you dislike about me? I asked you to be 100% honest.
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
If you win, what will you make them do?
19~ Who/when was your first “heartbreak”?
5~ When you first started having sex, was it what you thought it would be?
11~ Have you ever been caught by your parents or children or others while having sex?
50~ How many children do you have? What are their ages?
28~ What are some things that turn on? What is your biggest turn on?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
34~ Do you like the lights on or off during sex?
Do you watch it? What is your favorite?
10- List 5 of your top pet peeves.
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
13- What is the craziest/scariest thing you've ever done?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What was the longest? What was the shortest?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Get this wrong and this could mean the end… :-) some funny, some not…
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
6- Do you have dreams? Can you remember them? What do you usually dream about?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
9- If you could have three wishes, what would they be? Why?
What is your favorite toy? Ever wanted to try a specific toy?