What is the most interesting question you can ask to get to know someone?
15.06.2025 13:11
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
The Ice Breaker Questions
What firsthand information do you have on prisoner-on-prisoner sexual abuse/rape?
What have you learned about yourself that you did not before this?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
29~ What are some things that turn you off? What is your biggest turn off?
30~ What's something unexpected that turns you on?
48~ Do you have any siblings? Are you close to your family?
9- What’s your favorite season and why? What’s your least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Any that are a turn off?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
34- Ever been to a concert? What was your favorite? Who would you like to see?
PSA: Splatoon 3 On Switch Has Made Some Cuts To Keep Pace With Switch 2 - Nintendo Life
36~ What is your favorite time of day to have sex/make love?
44~ Care to share something about yourself that no one else knows about you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Why is my ex still keeping in touch with me even though she dumped me?
13- What is the craziest/scariest thing you've ever done?
1- What’s your favorite animal? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
If you win, what will you make them do?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
What is the best reply if your boyfriend asks you,"why do you love me?"
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
What would you do if you were lost at sea in the Florida Keys?
92~ Have you ever had or have an STD? How many? What was it?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
62~ Have you used adult toys?
What are some cool confidence hacks?
How many partners have you had oral sex with? Who? Care to Share?
49~ How many times have you been married? Why did they end?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
61~ How willing would you be to try new sexual positions?
12- What’s your favorite food? What’s your least favorite?
How well do you know me? And some of your thoughts about me
If NO, would you ever have one? Would it be with 2 men or 2 women?
47~ What would be your dream job and why?
What is one fantasy you have never told anyone about but really want to do?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
3- What Superhero or Superpower would you want to be/have?
29- How superstitious are you?
Is love natural, or is it somehow created?
Do you like it when they show and tell you what they want?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
25~ How do you feel about PDA? (Public Display of Affection)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
42~ What’s your biggest regret in life?
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?
81~ Do you have any kinks and/or fetishes?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
76~ Have you had a threesome? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
28- What are some things that people do that irritate you?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
52~ What are your hobbies?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
4- For a pet, Cat, dog or other?
3- Should Pluto still be considered a planet? 4- How about smoking?
5- Have you ever been hypnotized? Would you allow yourself to be?
14- What is an embarrassing moment in your life? How about your most embarrassing?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Would you read them together?
28~ What are some things that turn on? What is your biggest turn on?
Nothing too Serious
9- Is there something you’ve always wanted to ask me but you’re afraid?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What was the longest? What was the shortest?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
7-What do I do in bed that drives you wild? How about, what turns you off?
Would you ever want to be woken up with oral and/or intercourse?
Do you think this brought you closer together?
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?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
22- What is your favorite childhood memory? What is your least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
Please share Did you stop?
13- What’s your favorite drink? What’s your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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…
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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,
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
50~ How many children do you have? What are their ages?
Over time has your thoughts on sex changed?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
52~ Are you willing to make “those types” of bets with your partner?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
(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…)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Nurse/Patient Celebrity/Fan
Will you kiss after your partner has gone down on you? Swallow or spit semen?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Would you do it again, and would you rather 2 females or 2 males?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What is your favorite toy? Ever wanted to try a specific toy?
Do you like the “69” position? Do you prefer to be on top or bottom?
Would you allow me to clean every part of your body with my soapy hands and fingers?
33- Beach or Mountains? Or is there another place to like better?
How about if they talk dirty and/or call you names?
51~ What tends to bring a smile to your face?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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…
10~ How many dates are necessary before you to have sex with someone?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
15- What bad habit do you wish you could quit? Do you have any addictions?
How many times do you think you have “made love”?
70~ Would/do you have/like anal sex?
36- Do you play video games? What is your favorite? Do you a least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What is your view on sex? Meaning, When/Where/ How often/
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
34~ Do you like the lights on or off during sex?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
89~ Do you like taking showers together?
11- What's your favorite restaurant? What’s your least favorite?
Family Relation Age Play
Does the thought excite you? Care to share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
What have you learned about me that was new and/or surprising?
*** Deal Breaker Questions ***
67~ Do you like it when your partner moans and/or is vocal during sex?
1- What was your first impression of me? Has it changed?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
65~ Describe the best orgasm you’ve ever had? Care to share?
8- What are your thoughts on politics?
I would allow you to do it… What would you do to me?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Would /have you ever given your partner a lap dance and Striptease?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
*** Random Questions ***
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
*** Questions about Relationships/Past ***
71~ Would you give your partner a hand or foot job? Would you receive one?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
11- List at least 5 things on your bucket list. Have you done any of them already?
7- What if a person smells a certain way? 8- How about smoking?
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?
19~ Who/when was your first “heartbreak”?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Do you watch it? What is your favorite?
What is your favorite position? Why?
15- What's your favorite saying? What word or phrase is your least favorite?
How old are you? Male or Female?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Do you have a favorite? Is it ok if your partner does?
27- What was/ is nickname? Does it have a meaning behind it?
20- What’s your favorite candy? What’s your least favorite?
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)
21- What's your favorite way to spend a weekend or time off?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
15~ Have you ever been “in love”? Who? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
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?
You know that I will be 100% truthful, so ask.
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
That one or two things that made you go hmmmm, OMG or wow!
*** What’s Your Favorite…? ***
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Master/Slave Boss/Maid
9- If you could have three wishes, what would they be? Why?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Would you mind if your partner watched it? How about together vs alone?
37- Do you like your name? If you could change it, what would you change it too?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
10- List 5 of your top pet peeves.
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Can you Deep Throat? Do you like the taste of yourself?
84~ How do you feel about reading/listening to adult stories?
2- What’s your favorite color? Do you a least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
45~ How do you feel about me blindfolding you? How about blindfolding me?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
12- What is the weirdest thing you've ever eaten?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Have you ever? Care to Share?
If yes, what?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
7- What are your thoughts on religion? Is there an afterlife?
21~ What was the best date you ever went on? What has been the worst?
19- Do/have you smoked? What do you prefer? How often?
19- What’s your favorite fairytale? What’s your least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
48~ Have you ever paid or been paid for sex?
11- How about if they like a certain sports team? 12-How about drinking too much?
53~ How much can you tell me about the one thing you are most passionate about?
83~ How do you feel about Porn?
18- How often do you drink alcohol? What is your favorite drink?
What would you say to prove to yourself that it was really you?
3- What’s your favorite smell? Do you a least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Doctor/Nurse Stripper/Client
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Prisoner/Prison Guard Landlord/Tenant
11~ Have you ever been caught by your parents or children or others while having sex?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Escort/Client Job Applicant/Hiring Manager
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
31- If given a chance to be immortal, would you take it? Why?
17- What’s your favorite holiday? What’s your least favorite?
What do you dislike about me? I asked you to be 100% honest.
Get this wrong and this could mean the end… :-) some funny, some not…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
18~ Who/when was your first “crush”?
9~ How many times over your lifetime do you think you have had sex so far?
Model/Photographer Police/Criminal
39~ What are your love languages?
13- How about having a certain hair cut/style?
1~ How old were you when you had your first kiss? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
51~ Are you willing to play adult games with your partner?
* Give a rating for each one (0-100)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
14- What's your favorite dessert? Do you a least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
23- What is your dream job? What was it as a child?
26~ What side of the bed do you sleep on?
17- Have you ever done drugs? Which ones? How often?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
*** Questions About Me ***
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?
10- What is your favorite family tradition? What’s your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
32- What's your greatest talent? Can I see it right now?
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Teacher/Student Stranger/One Night Stand
82~ Do you have any fantasies involving Role-Playing?
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?
38~ Share your most embarrassing sexual memory?