What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 07:02
Do you like it when they show and tell you what they want?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
48~ Have you ever paid or been paid for sex?
Advice for trying GLP-1 drugs for weight loss from a doctor who's been there - NPR
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Do you think this brought you closer together?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Why do I sweat (mostly on face) when I eat usually spicy food?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
3- Should Pluto still be considered a planet? 4- How about smoking?
What caused the decline of the Soprano crew?
Would you allow me to clean every part of your body with my soapy hands and fingers?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
12- What’s your favorite food? What’s your least favorite?
Can you name an example of bad parenting?
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?
37- Do you like your name? If you could change it, what would you change it too?
The Aging Brain: 6 Things You Should Be Doing to Slow Cognitive Decline - CNET
1- What was your first impression of me? Has it changed?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
* Give a rating for each one (0-100)
What did someone say to you that instantly made you realize their life was in danger?
What is your favorite position? Why?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
What do you dislike about me? I asked you to be 100% honest.
Can someone write me a sex story?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Can the Beckham brand survive reports of family feud? - BBC
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Is there anything you did that you regret? If so, what is it, and why?
18- How often do you drink alcohol? What is your favorite drink?
Do you watch it? What is your favorite?
40~ What’s the weirdest place you’ve ever had sex?
What is your review of X-Men '97 season 1?
Nothing too Serious
22- What is your favorite childhood memory? What is 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,
Why cant I stop thinking about counsellor between sessions?
11~ Have you ever been caught by your parents or children or others while having sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Why are white women so hard to date?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
27- What was/ is nickname? Does it have a meaning behind it?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
(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 are your thoughts on politics?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
1~ How old were you when you had your first kiss? Who? Care to Share?
12- What is the weirdest thing you've ever eaten?
62~ Have you used adult toys?
38~ Share your most embarrassing sexual memory?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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…
34~ Do you like the lights on or off during sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
11- List at least 5 things on your bucket list. Have you done any of them already?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
84~ How do you feel about reading/listening to adult stories?
Nurse/Patient Celebrity/Fan
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
31- If given a chance to be immortal, would you take it? Why?
14- What is an embarrassing moment in your life? How about your most embarrassing?
What have you learned about yourself that you did not before this?
If yes, what?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Any that are a turn off?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Have you ever? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
5~ When you first started having sex, was it what you thought it would be?
That one or two things that made you go hmmmm, OMG or wow!
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
13- What is the craziest/scariest thing you've ever done?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
21~ What was the best date you ever went on? What has been the worst?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
*** Random Questions ***
Over time has your thoughts on sex changed?
Teacher/Student Stranger/One Night Stand
82~ Do you have any fantasies involving Role-Playing?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
60~ How important is oral sex? Do you like receiving? Do you like giving?
39~ What are your love languages?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
15~ Have you ever been “in love”? Who? Care to Share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
19~ Who/when was your first “heartbreak”?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would you mind if your partner watched it? How about together vs alone?
7-What do I do in bed that drives you wild? How about, what turns you off?
If YES, was it with 2 men or 2 women? Did you enjoy it?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
21- What's your favorite way to spend a weekend or time off?
47~ What would be your dream job and why?
Does the thought excite you? Care to share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
9- Is there something you’ve always wanted to ask me but you’re afraid?
23- What is your dream job? What was it as a child?
Model/Photographer Police/Criminal
52~ What are your hobbies?
Will you cheat again? How can, you be sure? Define what cheating is to you.
13- What’s your favorite drink? 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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
What was the longest? What was the shortest?
92~ Have you ever had or have an STD? How many? What was it?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
3- What’s your favorite smell? Do you a least favorite?
92~ Everyone needs a “safe” word. What is yours?
Escort/Client Job Applicant/Hiring Manager
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
80~ Share your top three fantasies/desires. (Be detailed) 😊
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
If you say it, I will stop, and we can talk about it when you are ready.
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?
How many times do you think you have “made love”?
Doctor/Nurse Stripper/Client
15- What's your favorite saying? What word or phrase is your least favorite?
19- Do/have you smoked? What do you prefer? How often?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
28~ What are some things that turn on? What is your biggest turn on?
44~ Care to share something about yourself that no one else knows about you?
83~ How do you feel about Porn?
10- List 5 of your top pet peeves.
Can you Deep Throat? Do you like the taste of yourself?
36~ What is your favorite time of day to have sex/make love?
13- How about having a certain hair cut/style?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Would you read them together?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Repairman/Lonely Wife Virgin/Experienced
5- Have you ever been hypnotized? Would you allow yourself to be?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
67~ Do you like it when your partner moans and/or is vocal during sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Get this wrong and this could mean the end… :-) some funny, some not…
70~ Would/do you have/like anal sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Prisoner/Prison Guard Landlord/Tenant
*** Deal Breaker Questions ***
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
20- What’s your favorite candy? What’s your least favorite?
18~ Who/when was your first “crush”?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
51~ Are you willing to play adult games with your partner?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
You know that I will be 100% truthful, so ask.
32- What's your greatest talent? Can I see it right now?
28- What are some things that people do that irritate you?
What is your favorite toy? Ever wanted to try a specific toy?
How well do you know me? And some of your thoughts about me
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If you win, what will you make them do?
Any that are a turn off?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
How old are you? Male or Female?
61~ How willing would you be to try new sexual positions?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
33- If you could visit any time period, when would you pick? Please explain why?
26~ What side of the bed do you sleep on?
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…
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?
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?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
1- What’s your favorite animal? Do you a least favorite?
What is your view on sex? Meaning, When/Where/ How often/
3- What Superhero or Superpower would you want to be/have?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? 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.
7- What are your thoughts on religion? Is there an afterlife?
9- What’s your favorite season and why? 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?
11- How about if they like a certain sports team? 12-How about drinking too much?
50~ How many children do you have? What are their ages?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Would you do it again, and would you rather 2 females or 2 males?
4- For a pet, Cat, dog or other?
25~ How do you feel about PDA? (Public Display of Affection)
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?
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?
Master/Slave Boss/Maid
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?
2- What’s your favorite color? Do you a least favorite?
89~ Do you like taking showers together?
*** What’s Your Favorite…? ***
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
*** Questions About Me ***
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
29- How superstitious are you?
81~ Do you have any kinks and/or fetishes?
7- What if a person smells a certain way? 8- How about smoking?
10~ How many dates are necessary before you to have sex with someone?
Would you ever want to be woken up with oral and/or intercourse?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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?
33- Beach or Mountains? Or is there another place to like better?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
9- If you could have three wishes, what would they be? Why?
15- What bad habit do you wish you could quit? Do you have any addictions?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
76~ Have you had a threesome? Care to Share?
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)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
17- Have you ever done drugs? Which ones? How often?
29~ What are some things that turn you off? What is your biggest turn off?
What have you learned about me that was new and/or surprising?
The Ice Breaker Questions
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
13~ Is there a difference between, making love, having sex, and fucking?
Do you have a favorite? Is it ok if your partner does?
14- What's your favorite dessert? Do you a least favorite?
*** Questions about Relationships/Past ***
49~ How many times have you been married? Why did they end?
10- What is your favorite family tradition? What’s your least favorite?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
30~ What's something unexpected that turns you on?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
65~ Describe the best orgasm you’ve ever had? Care to share?
9~ How many times over your lifetime do you think you have had sex so far?
51~ What tends to bring a smile to your face?
48~ Do you have any siblings? Are you close to your family?
What would you say to prove to yourself that it was really you?
I would allow you to do it… What would you do to me?
Please share Did you stop?
Family Relation Age Play
How many partners have you had oral sex with? Who? Care to Share?
42~ What’s your biggest regret in life?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
Do you like the “69” position? Do you prefer to be on top or bottom?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?