What is the most interesting question you can ask to get to know someone?
Last Updated: 16.06.2025 09:00
71~ Would you give your partner a hand or foot job? Would you receive one?
65~ Describe the best orgasm you’ve ever had? Care to share?
14- What's your favorite dessert? Do you a least favorite?
Phil Mickelson’s U.S. Open career likely ends with final bit of heartbreak - NBC Sports
Do you like the “69” position? Do you prefer to be on top or bottom?
18~ Who/when was your first “crush”?
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?
What's the biggest myth about illegal immigrants?
23- What is your dream job? What was it as a child?
Over time has your thoughts on sex changed?
89~ Do you like taking showers together?
Why do some men love sucking cocks?
The Ice Breaker Questions
How well do you know me? And some of your thoughts about me
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
How is it not psychopathic to use someone for sex, even if they agree?
Escort/Client Job Applicant/Hiring Manager
Will you cheat again? How can, you be sure? Define what cheating is to you.
10- List 5 of your top pet peeves.
Is Tinder the best dating app?
1~ How old were you when you had your first kiss? Who? Care to Share?
What is your view on sex? Meaning, When/Where/ 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…
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
9~ How many times over your lifetime do you think you have had sex so far?
Do you think this brought you closer together?
I have a bad reputation and need help. What should I do?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
1- What was your first impression of me? Has it changed?
7- What are your thoughts on religion? Is there an afterlife?
What is the cost of implementing synchronized traffic lights in a mid-sized city?
Any that are a turn off?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Have you ever? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
30~ What's something unexpected that turns you on?
Do you usually wear your panties over or under your pantyhose?
9- If you could have three wishes, what would they be? Why?
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,
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
11~ Have you ever been caught by your parents or children or others while having sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
*** What’s Your Favorite…? ***
What do you think is the most powerful line in the song "Non, Je Ne Regrette Rien" by Édith Piaf?
21- What's your favorite way to spend a weekend or time off?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
What is your favorite toy? Ever wanted to try a specific toy?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
If yes, what?
Do you have a favorite? Is it ok if your partner does?
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)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
3- What Superhero or Superpower would you want to be/have?
3- Should Pluto still be considered a planet? 4- How about smoking?
37- Do you like your name? If you could change it, what would you change it too?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Any that are a turn off?
5- Have you ever been hypnotized? Would you allow yourself to be?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
If you say it, I will stop, and we can talk about it when you are ready.
Doctor/Nurse Stripper/Client
If you win, what will you make them do?
10~ How many dates are necessary before you to have sex with someone?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What do you dislike about me? I asked you to be 100% honest.
Can you Deep Throat? Do you like the taste of yourself?
36- Do you play video games? What is your favorite? Do you a least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
Prisoner/Prison Guard Landlord/Tenant
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What have you learned about me that was new and/or surprising?
How old are you? Male or Female?
Do you like it when they show and tell you what they want?
Nothing too Serious
51~ What tends to bring a smile to your face?
11- List at least 5 things on your bucket list. Have you done any of them already?
44~ Care to share something about yourself that no one else knows about you?
13- What’s your favorite drink? What’s your least favorite?
12- What is the weirdest thing you've ever eaten?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
You know that I will be 100% truthful, so ask.
Would you do it again, and would you rather 2 females or 2 males?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
84~ How do you feel about reading/listening to adult stories?
60~ How important is oral sex? Do you like receiving? Do you like giving?
52~ Are you willing to make “those types” of bets with your partner?
Get this wrong and this could mean the end… :-) some funny, some not…
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Repairman/Lonely Wife Virgin/Experienced
2- What’s your favorite color? Do you a least favorite?
*** Random Questions ***
41~ Are there moments in your past that you would want to change? Please share 3 of them.
13~ Is there a difference between, making love, having sex, and fucking?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
6- Do you have dreams? Can you remember them? What do you usually dream about?
19- What’s your favorite fairytale? What’s your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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…
64~ When was your very first orgasm? When was your first from having sex? Care to share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
81~ Do you have any kinks and/or fetishes?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
25~ How do you feel about PDA? (Public Display of Affection)
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
9- What’s your favorite season and why? What’s your least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
How many partners have you had oral sex with? Who? Care to Share?
Please share Did you stop?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? 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…)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
52~ What are your hobbies?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would /have you ever given your partner a lap dance and Striptease?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
7-What do I do in bed that drives you wild? How about, what turns you off?
70~ Would/do you have/like anal sex?
83~ How do you feel about Porn?
33- Beach or Mountains? Or is there another place to like better?
*** Questions about Relationships/Past ***
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
29- How superstitious are you?
17- Have you ever done drugs? Which ones? How often?
22- Do you have any birth marks? How about scars? Care to share how you got them?
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?
26~ What side of the bed do you sleep 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?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Would you read them together?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
32- What's your greatest talent? Can I see it right now?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
51~ Are you willing to play adult games with your partner?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
21~ What was the best date you ever went on? What has been the worst?
How about if they talk dirty and/or call you names?
92~ Have you ever had or have an STD? How many? What was it?
Teacher/Student Stranger/One Night Stand
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!
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If YES, was it with 2 men or 2 women? Did you enjoy it?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
48~ Do you have any siblings? Are you close to your family?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
80~ Share your top three fantasies/desires. (Be detailed) 😊
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Does the thought excite you? Care to share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
28~ What are some things that turn on? What is your biggest turn on?
9- Is there something you’ve always wanted to ask me but you’re afraid?
31- If given a chance to be immortal, would you take it? Why?
* 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?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
12- What’s your favorite food? What’s your least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
53~ How much can you tell me about the one thing you are most passionate about?
38~ Share your most embarrassing sexual memory?
48~ Have you ever paid or been paid for sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
34- Ever been to a concert? What was your favorite? Who would you like to see?
19~ Who/when was your first “heartbreak”?
62~ Have you used adult toys?
Would you mind if your partner watched it? How about together vs alone?
What is your favorite position? Why?
Would you ever want to be woken up with oral and/or intercourse?
22- What is your favorite childhood memory? What is your least favorite?
19- Do/have you smoked? What do you prefer? How often?
11- What's your favorite restaurant? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
27- What was/ is nickname? Does it have a meaning behind it?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
39~ What are your love languages?
82~ Do you have any fantasies involving Role-Playing?
*** Deal Breaker Questions ***
3- What was the most surprising thing you’ve learned about me throughout our relationship?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
13- What is the craziest/scariest thing you've ever done?
15- What bad habit do you wish you could quit? Do you have any addictions?
7- What if a person smells a certain way? 8- How about smoking?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
42~ What’s your biggest regret in life?
4- For a pet, Cat, dog or other?
76~ Have you had a threesome? Care to Share?
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 would you say to prove to yourself that it was really you?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
How many times do you think you have “made love”?
29~ What are some things that turn you off? What is your biggest turn off?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
34~ Do you like the lights on or off during sex?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
18- How often do you drink alcohol? What is your favorite drink?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
61~ How willing would you be to try new sexual positions?
Master/Slave Boss/Maid
15~ Have you ever been “in love”? Who? Care to Share?
Nurse/Patient Celebrity/Fan
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
8- What are your thoughts on politics?
What was the longest? What was the shortest?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
49~ How many times have you been married? Why did they end?
Model/Photographer Police/Criminal
47~ What would be your dream job and why?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
If NO, would you ever have one? Would it be with 2 men or 2 women?
92~ Everyone needs a “safe” word. What is yours?
I would allow you to do it… What would you do to me?
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?
40~ What’s the weirdest place you’ve ever had sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
33- If you could visit any time period, when would you pick? Please explain why?
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?
1- What’s your favorite animal? Do you a least favorite?
13- How about having a certain hair cut/style?
Family Relation Age Play
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
28- What are some things that people do that irritate you?
11- How about if they like a certain sports team? 12-How about drinking too much?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
*** Questions About Me ***
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
10- What is your favorite family tradition? What’s your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Do you watch it? What is your favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
17- What’s your favorite holiday? What’s your least favorite?
50~ How many children do you have? What are their ages?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What have you learned about yourself that you did not before this?