180 Conversation Starters to Ask During the Talking Stage

Starting to talk to someone new? Yeah, it can be exciting and kind of awkward. You want to be interesting, not boring. Chill, not too chill. Flirty, but not too flirty.

The “talking stage” is that early phase where you’re just figuring each other out — what they like, how they think, and if there’s something real here.

As someone who’s seen more first messages than I’d like to admit, I’ve put together a list of conversation starters that actually work. Below, you’ll find tons of conversation starters that are casual, flirty, deep, or just plain fun.

Questions to Keep the Texting Vibe Going

1. Tell me the highlight of your day in emojis only.
2. What’s something random you saw today that made you think?
3. Send over your top 3 mood GIFs right now.
4. What’s your go-to meme when you need to laugh?
5. Rate your day from 1 to “I need a vacation.”
6. What snack are you craving right now?
7. Tell me something small that made you smile today.
8. What’s your weirdest shower thought recently?
9. If your phone could talk, what would it roast you for?
10. Describe your current vibe using a movie title.
11. What’s your most used emoji lately?
12. What’s a TikTok trend you secretly love?
13. If we were texting during a zombie apocalypse, what would you say first?
14. Send me a photo of your view right now (bonus if it’s cozy).
15. What’s your texting green flag?
16. Voice note or nah?
17. What’s one word to describe your mood today?
18. What’s your “ugh, I need to vent” topic lately?
19. If you had to send me a pic of something random right now, what would it be?
20. What time of day are you usually the funniest?

Getting-to-Know-You Questions

1. Are you more of an early bird or night owl?
2. What’s one thing that makes you feel grounded?
3. Do you thrive in chaos or prefer routines?
4. How do you usually spend your weekends?
5. Are you the “planner” in your group or more go-with-the-flow?
6. What’s your love-hate relationship with adulting?
7. What’s your favorite kind of day—rainy, sunny, or cloudy and cozy?
8. Do you recharge alone or around people?
9. What’s one value that’s super important to you?
10. How do you usually deal with stress?
11. What’s your relationship with social media like?
12. Do you need a lot of space or love staying connected?
13. What’s a habit you’re proud of building?
14. Are you more of a big-picture thinker or detail-oriented?
15. Do you get energy from trying new things or sticking to what you know?
16. What does your “perfect normal day” look like?
17. Are you usually the listener or the talker?
18. What kind of people do you feel most at ease around?
19. Are you more spontaneous or intentional with your decisions?
20. How would your friends describe your vibe?

Flirty and Romantic Questions

1. So, what do you think makes someone instantly attractive?
2. What’s your idea of a perfect slow Sunday with someone?
3. Would you say you’re more of a good morning text or goodnight call kind of person?
4. Have you ever had a crush on someone you barely knew?
5. What kind of flirting works best on you?
6. If we were on a date right now, where would we be?
7. What’s something really small someone can do that makes you melt a little?
8. Do you believe in “the spark” or slow-build connections?
9. What kind of compliments actually make you feel seen?
10. Would you ever go on a spontaneous weekend trip with someone you like?
11. What’s your take on PDA — yay or nah?
12. What kind of message makes you instantly smile when you see it?
13. Do you believe in love at first sight — or at first text?
14. What’s something cute you wish more people did when they like someone?
15. If we were in a rom-com, what scene would we be in right now?
16. What’s your favorite thing about getting to know someone new?
17. Would you rather a grand romantic gesture or low-key, consistent affection?
18. What’s your love language — and do you think it’s obvious?
19. What’s one thing someone did that made you feel really special?
20. Do you think texting can be just as intimate as talking in person?

Past Experiences

1. What’s a memory that still makes you laugh out loud?
2. Have you ever gone on a trip that totally changed your mindset?
3. What’s the most unexpected thing that’s happened to you?
4. What’s a childhood moment you’ll never forget?
5. Have you ever had a “this could be a movie” type of day?
6. What was your first-ever job like?
7. Have you ever had a completely embarrassing moment that’s funny now?
8. What’s the weirdest coincidence you’ve experienced?
9. Did you ever get into big trouble as a kid?
10. What’s one decision you made that you’re glad you did?
11. What’s something your younger self would be surprised about now?
12. Have you ever had a weird or hilarious dream that stuck with you?
13. What’s the most spontaneous thing you’ve done?
14. Have you ever had a “plot twist” moment in life?
15. What’s something small that felt like a big deal at the time?
16. Ever had a total stranger make your day better?
17. What’s one moment you’d relive if you could?
18. What’s your most “main character” moment so far?
19. What’s a hobby or activity you’ve totally outgrown?
20. Have you ever had a terrible first date story?

Values and Beliefs

1. What’s something you genuinely value in a relationship?
2. How do you define “being a good person”?
3. What’s a belief or opinion you’ve changed your mind about over the years?
4. What’s something that grounds you when life feels chaotic?
5. Are you more of a “follow your heart” or “trust your logic” type?
6. How do you handle conflict when it comes up?
7. What does emotional safety look like to you?
8. What’s something you wish more people understood about you?
9. What makes you feel genuinely appreciated?
10. Are you someone who needs space or closeness during tough times?
11. What kind of support means the most to you?
12. What do you think builds trust — and what breaks it?
13. How do you usually show love or care for someone?
14. What’s a cause or issue you care about deeply?
15. Are you more of a forgiving or “I need time” person?
16. How do you define success in your own life?
17. What’s something non-material that makes you feel rich?
18. What’s a “green flag” you really appreciate in people?
19. How do you decide if someone’s worth opening up to?
20. Do you believe everything happens for a reason, or do we create our own meaning?

Dreams, Goals, and Aspirations

1. What’s a goal you’re working on right now?
2. If money wasn’t a factor, what would you spend your time doing?
3. Is there something you’ve always wanted to learn but haven’t yet?
4. Do you have a dream place you’d love to live one day?
5. What’s something you want to try at least once in your life?
6. What motivates you when you’re feeling stuck?
7. Is there a skill you’ve picked up recently that you’re proud of?
8. Do you daydream more about the future or reflect on the past?
9. What does “success” look like for you personally?
10. What’s your idea of a fulfilling life?
11. If you had one free year, how would you spend it?
12. Is there something from your bucket list you’ve already crossed off?
13. What’s something you’d like to be known for?
14. What career path would you explore if you could start fresh?
15. What helps you stay inspired?
16. Have your goals changed a lot over the years?
17. What’s one thing you hope your future self thanks you for?
18. Is there a dream you’ve never told anyone?
19. What’s something you’d love to create or build?
20. Who or what influences your goals the most?

“This or That” and Quick Pick Questions

1. Coffee or tea in the morning?
2. Movies at home or night out?
3. Text first or call later?
4. Sweet or salty snacks?
5. Early bird or night owl?
6. Dogs or cats?
7. Music on full blast or soft in the background?
8. Beach vacation or city trip?
9. Hoodie weather or tank top season?
10. Book or podcast?
11. Sunrise or sunset?
12. Spicy food or mild?
13. Stay in or go out on a Friday night?
14. Pancakes or waffles?
15. Concerts or cozy nights in?
16. Long texts or quick memes?
17. Ice cream in winter or hot chocolate in summer?
18. Group hangouts or one-on-one time?
19. Spontaneous or well-planned?
20. Karaoke star or silent observer?

Hypothetical and “What If” Scenarios

1. If you could live anywhere for a year, where would you go and why?
2. If you had one extra hour every day just for yourself, how would you spend it?
3. If you could relive one day of your life without changing anything, which day would you pick?
4. If money didn’t matter, what kind of work or project would you spend your time on?
5. If you could instantly gain confidence in one area of your life, what would it be?
6. If your future self sent you a message, what would you hope it says?
7. If you had to describe your dream weekend getaway, what would it include?
8. If you could undo one decision without affecting who you are now, what would it be?
9. If you had to teach a class about something you’re passionate about, what would it be?
10. If you could spend the day with someone (alive or dead), who would you pick and what would you talk about?
11. If you could only hold on to three core values for life, what would they be?
12. If you had to live one day over and over Groundhog Day-style, what would you want it to be?
13. If you could change one thing about how people date today, what would it be?
14. If you woke up tomorrow with no fear, what’s the first thing you’d do?
15. If you had the chance to completely start over somewhere new, would you take it?
16. If you could guarantee one thing about your future, what would you want it to be?
17. If your younger self met you now, what do you think they’d be proud of?
18. If someone wrote a book about your life, what chapter would the talking stage be?
19. If you had to choose one memory to keep forever, even if you lost the rest, what would it be?
20. If falling in love had a soundtrack, what song would play the moment you knew?

Entertainment and Everyday Favorites

1. What show do you rewatch when you need comfort?
2. Which movie do you quote way too often?
3. Who’s your favorite underrated celebrity?
4. What’s your go-to song when you need a mood boost?
5. Are you more into music festivals or solo headphone vibes?
6. Do you have a favorite guilty pleasure show?
7. If you could only listen to one artist for a year, who would it be?
8. What’s a fictional character you low-key relate to?
9. What’s a movie you’ll never get tired of?
10. Team binge-watching or one-episode-a-week?
11. What’s your favorite thing to cook (or order in)?
12. Are you into podcasts? Got any recs?
13. What’s your comfort movie snack combo?
14. Do you keep up with celeb drama or avoid it?
15. What’s one viral trend you secretly loved?
16. Which fictional world would you totally live in?
17. Are you more into Spotify playlists or YouTube rabbit holes?
18. What’s a book or series that stuck with you?
19. What’s your favorite thing to do on a chill night?
20. What’s something totally ordinary that you love?

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