Every time I have a new crush, I simply lose it – I have no idea how to behave. Most of the time, I have either managed to get all shy and awkward with my crush or simply ended up in a TMI situation. All those quirky observations you had planned to ask your partner might just disappear from your head.
And I have been in such a spot – those experiences, in reality, motivated me to come up with the top 100 freaky questions to ask your crush or partner. You don’t need to come up with insightful thoughts or sharp jokes to impress your crush. Instead, you can roll the ball in your crush’s court every time you are worried.
And this is where I can help you improve. Stay tuned to find out more.
100 Freaky Questions To Ask Your Crush Or Partner!
There are so many different questions that you can ask your crush or partner – no wonder the list of freaky questions to ask your crush is huge. You just have to figure out which ones to ask and which ones to save for the near future. So, without wasting any more time, scroll down and keep up with all the questions to ask your crush!
1. Dirty Questions To Ask Your Crush
While wondering what the top freaky questions to ask your crush are, you will come across different themes. But my favorite questions are always leaning on the dirtier side of romance – #sorrynotsorry, but here’s my personal list of dirty questions to ask your crush or even your partner, for that matter.
- How do you feel about one-night stands?
- After a one-night stand, what do you prefer – breakfast in bed or no contact?
- What do you find hot about me?
- What do you wear to bed?
- Do you like it if someone else makes the first move?
- What’s your favorite body part of a romantic partner?
- Do you like hair-pulling?
- What is your most embarrassing sexual fantasy?
- How many people have you done it with?
- Do you like being blindfolded?
- Have you ever done it with more than one person at a time?
- Do you love getting insulted inside the bedroom?
- Do you like getting spanked or taking pleasure in doing the spanking?
- Have you ever role-played?
- Would you ever do it in a place where you might get caught?
- Have you ever done it with a stranger online?
- Have you ever done a strip tease?
- Have you ever given a lap dance to someone?
- Have you ever faked an orgasm?
- Have you ever pleasured yourself while thinking about me?
2. Romantic Questions To Ask Your Crush
As I just mentioned, finding freaky questions to ask your crush is a different experience for different people. While I can choose to ask a flirty, dirty question, you can choose romance. And this is why I have decided to cater to multiple themes.
So, without wasting much time, stay tuned to find out the top romantic questions to ask your crush!
- What are we doing on our next date?
- Have you ever been in love?
- What’s your love language?
- Would you change anything about the way we met?
- How do you feel about serious relationships?
- Do you want to have coffee sometime?
- What’s your ideal date night?
- What’s the most romantic thing someone’s done for you?
- Do you believe in soulmates?
- What do you like about being in a relationship?
- Do you fall in love easily?
- What’s something you want to do differently in your next relationship?
- What’s the most romantic thing you’ve ever done for someone?
- Do you believe in monogamy?
- Do you have any relationship deal-breakers?
- What are your relationship red flags?
- Have you ever cheated on a significant other?
- Have you ever been cheated on?
- What’s been your hardest breakup?
- How do you feel about PDA?
3. Flirty Questions To Ask Your Crush
Flirting is healthy – at least, that’s what I like believing when I am crushing on someone. And guess what? It’s that time of the year again, and I have a crush on someone unattainable at work (he already has a ‘girl’), but that doesn’t mean I can’t ask my crush a few flirty questions and act dumb.
Scroll down to check out the flirty questions to ask your crush!
- Do I make you nervous?
- Do you miss any of your exes?
- What’s an automatic swipe right for you?
- What’s your most memorable kiss?
- What would you do if I kissed you?
- Would you ever go skinny dipping?
- Have you ever had a dirty thought about me?
- Is it okay to kiss on the first date?
- What’s the sexiest thing about you?
- Would you rather cuddle or make out?
- Do you like being teased, or do you enjoy the teasing?
- What would you do if I sent you a dirty picture right now?
- What would you do if you walked in on me pleasuring myself thinking about you?
- When was the last time you touched yourself?
- What is your favorite kind of foreplay?
- If you owed me a sexual favor, how would you make it worth my while?
- How often would you like to do it with me in a week?
- How do you feel about open relationships?
- How do you feel about love bites?
- What is the dirtiest scenario you’ve imagined with me?
4. Questions To Ask Your Boyfriend
You might be thinking, why am I talking about things to ask your boyfriend when this article is all about the top freaky questions to ask your crush? TBH, I had almost forgotten how it feels to be in love with your boyfriend, even after dating for a long time. But isn’t that the beauty of being in love? Stay tuned to find out!
- How old were you when you lost your virginity?
- What’re the most times you’ve had sex in a 24-hour period?
- What’s your favorite sex position?
- What do you prefer – early-morning sex or late-night romance?
- What are the three things about me that instantly turns you on?
- Where should I touch myself when we video call later tonight?
- What do you believe in – love at first sight or lust at first sight?
- What kind of outfit would you like to see me in?
- What would you do if you saw me naked right now?
- What would you do if I answered the door in your favorite lingerie when you came back home post work later tonight?
- What’s your favorite kissing spot?
- Do you like it when I go down on my knees for you?
- What’s your favorite type of underwear on me?
- What’s your number one kink that gets you off every time without fail?
- Are you a member of the Miles High Club?
- What’s your favorite porn?
- Do you like it when I talk dirty with you?
- Do you check me out when I walk away from you?
- What’s the craziest thing you have ever done inside the bedroom?
- Where would you start if you do have to give me a full body massage?
5. Questions To Ask Your Girlfriend
It is only fair that I also discuss the crazy things to ask your girlfriend while we are already discussing all kinds of fun conversation starters. Sometimes, the questions you ask your girlfriend are different from the ones you ask your girl crush.
Keeping that difference in mind, scroll down to find the questions to ask a girl you are crushing on or even your girlfriend.
- Where’s the hottest place you’ve had sex?
- What was your first time like?
- What’s your favorite sex toy?
- What’s your favorite sexual fantasy?
- Did I make you wet…yet?
- What do you prefer – slow and gentle or quick and rough?
- Which of my pictures has turned you on the most today?
- When was the last time you masturbated?
- What do you like – lights off or lights on?
- What’s the most unexpected thing that can turn you on at the wrong time?
- What’s the first thing you notice about a guy when you are on a date with them?
- What are the biggest turn-offs in a guy, according to you?
- Have you ever made the first move on an unsuspecting guy?
- Do you like it when a man takes charge, especially when you are in bed?
- What is the hottest thing you can wear…for me?
- What’s the most intimate thing that couples do that’s not really physical?
- How do you feel about whipped cream or chocolate sauce, for that matter?
- What’s your favorite location for a naughty, romantic getaway?
- Are you willing to try out new things?
- How often should we take long, romantic showers together?
Bonus Section: 20+ Freaky Questions to Ask Your Crush, IRL Or Text
Welcome to The Dating Dairy’s bonus section! I was just about to finish this blog then I remembered there are some questions that keep popping up inside my head, but they don’t really fit into any category. And after speaking to several others, I am convinced I am not the only one with these doubts.
So, here we go!
- “Do you like to cook, or are you Team Takeout?”’
- “What’s the best (or craziest) trip you’ve ever been on?”
- “What’s your favorite thing to make/favorite restaurant to order from?”
- “What’s your favorite time of year?”
- “What do you look for in a partner?”
- “Do you remember your first kiss?”
- “How long do you think it takes to fall in love with someone?”
- “Where would you take me on our first date?”
- “Do you think you’re a good kisser?”
- “What do you think is the most attractive thing about you?”
- “What would you do if I kissed you right now?”
- “What’s your flirting style?”
- “What are your thoughts on monogamy?”
- “When was your last relationship?”
- “Do you think you’re over your ex?”
- “What’s the most ridiculous thing you’ve ever bought for yourself?”
- “Would you ever fake a sick day? If so, how would you spend it?”
- “What are your guilty pleasures?”
- “Do you want to be in a relationship right now?”
- “What do you think is your biggest flaw?”
- “Do you think it’s better to stay friends with exes or to cut ties with them?”
- “What are your biggest turn-ons?”
And It’s A Wrap!
And that’s a wrap on the top hundred freaky questions to ask your crush! Obviously, you can save this article so that you can check out your favorite questions when you need them. The other day, I was completely awkward with my crush – I literally said ‘hi,’ and then I had nothing else to say, which was SO weird.
It’s best to have a few quirky questions up your sleeves to ask your crush or even your partner whenever you feel like it. What do you think? Share your thoughts and experiences related to the topic with us in the comments below.
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