What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 00:00
Teacher/Student Stranger/One Night Stand
51~ What tends to bring a smile to your face?
21~ What was the best date you ever went on? What has been the worst?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
How many times do you think you have “made love”?
28- What are some things that people do that irritate you?
Family Relation Age Play
12- What’s your favorite food? What’s your 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?
How can MeTV Toons compete with other national broadcast TV networks?
62~ Have you used adult toys?
7- What are your thoughts on religion? Is there an afterlife?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Why do so many 18 to 29-year-old men struggle in dating?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Have you ever? Care to Share?
42~ What’s your biggest regret in life?
Common herbal supplement used to beat stress linked to liver toxicity - Times of India
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
26~ What side of the bed do you sleep on?
3- What Superhero or Superpower would you want to be/have?
What are some of the most annoying movie clichés?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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)
51~ Are you willing to play adult games with your partner?
Why would Trump make conspiracy claims that Haitians are eating pets in Ohio?
Any that are a turn off?
Would you mind if your partner watched it? How about together vs alone?
84~ How do you feel about reading/listening to adult stories?
What does it mean to you to live a life that reflects biblical values?
48~ Do you have any siblings? Are you close to your family?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Is the Chinese economy currently collapsing? If not, what could potentially cause it to collapse?
Over time has your thoughts on sex changed?
36~ What is your favorite time of day to have sex/make love?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
3- What’s your favorite smell? 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…)
8- What's your favorite flavor of ice cream? Do you a least favorite?
How do women feel when they are in love?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
23- What is your dream job? What was it as a child?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
76~ Have you had a threesome? Care to Share?
70~ Would/do you have/like anal sex?
Do you think this brought you closer together?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
9- If you could have three wishes, what would they be? Why?
34- Ever been to a concert? What was your favorite? Who would you like to see?
9- What’s your favorite season and why? What’s your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
29~ What are some things that turn you off? What is your biggest turn off?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
7-What do I do in bed that drives you wild? How about, what turns you off?
13~ Is there a difference between, making love, having sex, and fucking?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
48~ Have you ever paid or been paid for sex?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
If NO, would you ever have one? Would it be with 2 men or 2 women?
10- List 5 of your top pet peeves.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
20- What’s your favorite candy? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
13- How about having a certain hair cut/style?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Master/Slave Boss/Maid
14- What's your favorite dessert? Do you a least favorite?
What do you dislike about me? I asked you to be 100% honest.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
*** Deal Breaker Questions ***
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
39~ What are your love languages?
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?
10- What is your favorite family tradition? What’s your least favorite?
4- For a pet, Cat, dog or other?
Do you have a favorite? Is it ok if your partner does?
Get this wrong and this could mean the end… :-) some funny, some not…
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
52~ What are your hobbies?
13- What is the craziest/scariest thing you've ever done?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
44~ Care to share something about yourself that no one else knows about you?
15- What's your favorite saying? What word or phrase is your least favorite?
50~ How many children do you have? What are their ages?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
*** Questions about Relationships/Past ***
11- List at least 5 things on your bucket list. Have you done any of them already?
83~ How do you feel about Porn?
Can you Deep Throat? Do you like the taste of yourself?
Do you like the “69” position? Do you prefer to be on top or bottom?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
71~ Would you give your partner a hand or foot job? Would you receive one?
49~ How many times have you been married? Why did they end?
67~ Do you like it when your partner moans and/or is vocal during sex?
34~ Do you like the lights on or off during sex?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
92~ Everyone needs a “safe” word. What is yours?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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/
Would you do it again, and would you rather 2 females or 2 males?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would you ever want to be woken up with oral and/or intercourse?
28~ What are some things that turn on? What is your biggest turn on?
1- What’s your favorite animal? Do you a least favorite?
18- How often do you drink alcohol? What is your favorite drink?
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
Nothing too Serious
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Would you read them together?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
12- What is the weirdest thing you've ever eaten?
What was the longest? What was the shortest?
The Ice Breaker Questions
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
You know that I will be 100% truthful, so ask.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
38~ Share your most embarrassing sexual memory?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
*** Questions About Me ***
47~ What would be your dream job and why?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
That one or two things that made you go hmmmm, OMG or wow!
How about if they talk dirty and/or call you names?
1- What was your first impression of me? Has it changed?
82~ Do you have any fantasies involving Role-Playing?
5- What do I do outside the bedroom that turns you on? 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?
17- What’s your favorite holiday? What’s your least favorite?
11- What's your favorite restaurant? What’s your least favorite?
Would /have you ever given your partner a lap dance and Striptease?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
30~ What's something unexpected that turns you on?
8- What are your thoughts on politics?
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,
7- What if a person smells a certain way? 8- How about smoking?
19- What’s your favorite fairytale? What’s your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
32- What's your greatest talent? Can I see it right now?
* Give a rating for each one (0-100)
If yes, what?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
*** What’s Your Favorite…? ***
If you win, what will you make them do?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Nurse/Patient Celebrity/Fan
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Doctor/Nurse Stripper/Client
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
52~ Are you willing to make “those types” of bets with your partner?
36- Do you play video games? What is your favorite? Do you a least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
81~ Do you have any kinks and/or fetishes?
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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
21- What's your favorite way to spend a weekend or time off?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Please share Did you stop?
Repairman/Lonely Wife Virgin/Experienced
Escort/Client Job Applicant/Hiring Manager
65~ Describe the best orgasm you’ve ever had? Care to share?
What have you learned about yourself that you did not before this?
9- Is there something you’ve always wanted to ask me but you’re afraid?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
*** Random Questions ***
18~ Who/when was your first “crush”?
22- What is your favorite childhood memory? What is your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
19- Do/have you smoked? What do you prefer? How often?
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…
11- How about if they like a certain sports team? 12-How about drinking too much?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
27- What was/ is nickname? Does it have a meaning behind it?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
25~ How do you feel about PDA? (Public Display of Affection)
Any that are a turn off?
What have you learned about me that was new and/or surprising?
33- Beach or Mountains? Or is there another place to like better?
40~ What’s the weirdest place you’ve ever had sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
15- What bad habit do you wish you could quit? Do you have any addictions?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Prisoner/Prison Guard Landlord/Tenant
11~ Have you ever been caught by your parents or children or others while having sex?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
17- Have you ever done drugs? Which ones? How often?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
I would allow you to do it… What would you do to me?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
3- Should Pluto still be considered a planet? 4- How about smoking?
Do you like it when they show and tell you what they want?
9~ How many times over your lifetime do you think you have had sex so far?
10~ How many dates are necessary before you to have sex with someone?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
33- If you could visit any time period, when would you pick? Please explain why?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
61~ How willing would you be to try new sexual positions?
Model/Photographer Police/Criminal
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
60~ How important is oral sex? Do you like receiving? Do you like giving?
How many partners have you had oral sex with? Who? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?
2- What’s your favorite color? Do you a least favorite?
Does the thought excite you? Care to share?
What is your favorite position? Why?
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…
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
19~ Who/when was your first “heartbreak”?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
89~ Do you like taking showers together?
13- What’s your favorite drink? What’s your least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
31- If given a chance to be immortal, would you take it? Why?
53~ How much can you tell me about the one thing you are most passionate about?
If you say it, I will stop, and we can talk about it when you are ready.
29- How superstitious are you?
What would you say to prove to yourself that it was really you?
Do you watch it? What is your favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
92~ Have you ever had or have an STD? How many? What was it?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
How old are you? Male or Female?