No Dead Ends: Kill the "Yes/No" Answers. Always ask open-ended questions. If they can answer with one word, you’ve lost. Frame your questions to require a story or an opinion to keep the momentum alive. If you're still feeling nervous, brush up on your basics with our guide on How to talk to strangers online.
The Pro Hack: Don't go in cold. Use their Instagram/TikTok stories or Wakie posts as a natural bridge. Commenting on something they already shared is the ultimate low-pressure conversation starter.
What questions to ask your crush? 101+ Question Cheat Sheet
Part 1: Chill Starters & First Meeting
What’s the most "main character" thing that happened to you this week?
If you were an NPC in a video game, what would be your side quest?
What’s your current hyperfixation?
Best street food you’ve ever had?
What’s the weirdest Wikipedia rabbit hole you’ve fallen down?
Are you a "morning person" or a "3 AM philosopher"?
If you could delete one app from existence, what would it be?
What’s your "guilty pleasure" movie?
What’s the most chaotic thing you’ve seen lately?
Send me the 5th meme in your saved folder. No context.
What’s your "comfort" YouTube channel?
What’s the best compliment you’ve ever received?
If you had a theme song, what would it be?
What’s your "Roman Empire" (something you think about daily)?
What’s the most overrated holiday?
If you could have any superpower, but only for 10 minutes a day, what would it be?
What’s a hobby you’d start if money wasn't an issue?
What’s the most "aesthetic" place you’ve ever visited?
What’s your go-to karaoke song?
What’s your favorite way to spend a rainy Sunday?
What’s the most "unhinged" travel story you have?
Best advice you’ve ever actually ignored?
What’s your current "on repeat" song that you’re not tired of yet?
If you could speak to one species of animal, which one would it be?
If you had to change your first name, what would you pick?
Part 2: Flirty Texting & Digital Rizz
Stuck behind a screen? Building digital chemistry is an art.
I just saw something that reminded me of you... want to guess what?
What’s your favorite way to be "annoyed" by someone?
Rate my current vibe in three emojis.
What was your first impression of me?
If we were stuck in a 24-hour layover, how would we kill time?
What’s one thing I shouldn't know about you yet?
What’s the most spontaneous thing you’ve done recently?
If you could see me right now, what do you think I’m doing?
What’s your "type" in three words?
What’s a secret talent you have?
What’s your favorite physical feature on yourself?
What’s your favorite way to be complimented?
What’s something you’ve always wanted to try but were too scared?
If you could change one thing about your personality, what would it be?
What’s your favorite childhood memory?
What’s the most "cliché" thing you actually love?
What’s the last thing that made you laugh until you cried?
What’s your favorite thing to do on a first date?
If we were in a horror movie, who would die first?
Do you believe in "love at first sight" or should I walk by again?
What’s a "hot take" you have that most people disagree with?
What’s the most chaotic photo in your camera roll right now?
What’s your favorite emoji to use ironically?
If we had to share a pair of headphones, what are we listening to?
Part 3: The "21 Questions" Game
What’s your proudest achievement so far?
If you could have dinner with anyone, dead or alive, who would it be?
What’s the biggest lesson you learned from your last relationship?
What’s your "love language"?
What’s one thing you’ll never do again?
What’s your idea of a perfect day?
If you could live anywhere in the world, where would it be?
What’s the most adventurous thing you’ve ever done?
What’s your biggest "dealbreaker"?
Do you believe in soulmates?
What’s a habit you’re trying to break?
What’s your favorite thing about yourself?
What’s the best advice you’ve ever been given?
What’s something you’re passionate about?
What’s your biggest regret?
If you could go back in time, what year would you go to?
What’s your dream job?
What’s one thing that always makes you smile?
What’s your favorite book or movie of all time?
Are you a "live in the moment" or a "plan for the future" person?
What’s something you’ve always wanted to learn?
What’s the most meaningful gift you’ve ever received?
What’s your favorite way to de-stress?
What's your biggest "what if" in life?
What is your biggest fear?
What’s a "green flag" you look for that most people overlook?
What’s the most spontaneous trip you’ve ever taken?
If you could swap lives with a fictional character for a day, who would it be?
What’s the most important thing you’ve learned about yourself this year?
What’s something you’re proud of that no one knows about?
What’s a quality you admire most in others?
If you could change one thing about the world, what would it be?
What’s the most difficult thing you’ve ever had to do?
How do you handle failure?
What’s your philosophy on life?
What’s the most important thing to you in a relationship?
How have you changed in the last five years?
What’s a dream you’ve never told anyone?
What do you want to be remembered for?
What’s something you’ve struggled with that made you stronger?
What’s your favorite thing about your life right now?
What’s a question you wish people would ask you more often?
How do you define success?
What’s the most important lesson life has taught you?
What’s a risk you took that paid off?
What’s your biggest goal for 2025?
What makes you feel the most "alive"?
If you could ask me anything and I had to answer honestly, what would it be?
How do you show love when you're not in a "romantic" mood?
What’s a truth about yourself you’ve recently had to accept?
If you could leave a message for your future self 10 years from now, what would it say?
How do you handle it when your "social battery" runs out?
How to Keep it Going: Quick Fixes for Awkward Silences
Let’s be real: even with a list of 101 "rizz-ready"questions in your pocket, conversations can still hit a wall. Maybe they’re shy, maybe they’re having a bad day, or maybe you’re just overthinking it. The secret to infinite conversation isn't having the perfect topic; it’s about knowing how to pivot when the energy drops. Think of it like a game of tennis - if the ball stops moving, the game is over. Here is how you jump-start the momentum when things start feeling a little too quiet.
How to Fix a Dry Conversation
The "I Remember" Hook: Bring up something they mentioned 10 minutes ago. It shows you actually care.
The "Random Observation" Play: Comment on something happening around you or a weird thought you just had.
Call it Out (Playfully): "Wait, are we really about to talk about the weather? We're better than this."
Knowing When to Stop: Signs They Aren't Vibing
The One-Word Plague: If you get "lol" or "cool" three times in a row, match their energy and move on.
Zero Follow-Up: If they answer but never ask back, the energy is one-sided.
The "Wakie Method": Practice Your Rizz on Human Mode
Stop practicing on your crush - the stakes are too high.
Stop carrying the conversation on your back. If you’re getting one-word replies, switch from "interrogation mode" to sharing vibes:
Send a "Visual Hook": Share a chaotic meme or a cool photo from your day without adding a question.
The 3-Strike Rule: If they don't engage after three "no-pressure" texts, match their energy and lean back.
Know Your Worth: If they stay dry, they aren't matching your energy - don't waste your rizz on someone who isn't giving anything back.
Not if you use the "Why" Game. If you’re talking about movies, ask why that specific one moved them. Deep talk is about the reason behind the preference.
3 things to avoid: 1. Generic compliments. 2. Double texting. 3. Overusing emojis.
Focus on questions that reveal their interest in you, like "What was your first impression of me?" If they give detailed answers, they’re definitely vibing. See our full list in Part 3 above.