Last Updated on November 25, 2022 by Alexander Burgemeester
Impressing someone often comes down to your conversation skills. Are you able to keep a good discussion going- or do you become awkward and boring?
Can you keep a girl wanting to text back- or does she drift in and out of responding? Are you getting the dreaded one-word text from your crush?
First, you need to remember that everyone is different. While a healthy relationship entails a mutual level of safety and connection, different people prioritize different needs.
Some people want straight humor all the time. Others want to have deeper and more intimate discussions. Neither scenario is better or worse than the other. But you need to be paying attention to see what she values.
You also need to consider general texting rules (avoid double-texting, don’t send excessively long paragraphs, and be mindful of which emojis you use).
Following those rules will increase the chance of you impressing your crush- and keeping their attention!
Here are some of the best things to talk about over text:
Basic Questions to Ask to Keep the Conversation Going
Open-ended questions are the best questions for maintaining the flow of your text conversation. Don’t overthink them, especially when you’re just getting to know someone.
If you’re on a dating app and talking to several people, you’ll want to embrace the skill of asking open-ended questions. The more you practice it, the easier it becomes.
At this point, you’re just gathering all the details of who they are and what they like. Fun questions that focus on their personality tend to be the safest bet. Bonus points if it leads to her asking open-ended questions back to you!
Casual Getting-To-Know-You Conversation Starters
When you’re first getting to know someone, you want to have fun going back and forth asking and answering questions.
At this point, there shouldn’t be too much pressure. If things become too serious, it may send the wrong message.
#1 What’s Your Favorite Food?
This question also opens the door to many other questions, like asking about their favorite restaurant, whether they like to cook, and if they’re more into sweets or savory dishes.
If you’re trying to plan a first date, knowing this answer can be tremendously helpful!
#2 Who’s Your Celebrity Crush?
Most of us have imagined being with a celebrity at some point or another.
This is a lighthearted conversation that can give you a feel for your crush’s preferences, particularly when it comes to someone’s appearance.
#3 Do You Have Any Hidden Talents?
Can you crush juggle like a professional? Speak four languages? Bake a perfect cake?
Their answer might surprise you!
#4 Who’s the Funniest Person You Know?
Maybe it’s you! And if it’s not, you should definitely find out what makes her laugh!
#5 What’s Your Favorite Part of Your Day?
What does your crush look forward to the most when they wake up in the morning? Is it their spin class? Walking their dog after dinner? Drinking that first cup of coffee?
#6 What’s Your Zodiac Sign?
Even if you aren’t necessarily into astrology, you may be into talking about each other’s horoscopes (and whether you’re compatible or not).
You can also ask when your crush’s birthday is- and be sure to save that information for later!
#7 What’s a Hobby You’ve Always Wanted to Try?
You can also follow up with asking why they haven’t tried it yet.
Find out what they like to do in their free time- that will help you for planning how you can spend time together in person.
#8 What’s Your Biggest Pet Peeve?
If there’s one thing you need to know about your crush, it’s what not to do around them. Their answer can help you avoid making that mistake.
#9 What Was Your First Concert (Or Last Concert?)
If you’re into music, this is a great question to ask. If you find out you both like similar artists, you two will have plenty to talk about!
#10 What Game Did You Love to Play as a Kid?
It’s a fun thing to revisit childhood. Maybe you two enjoyed the same games!
#11 What’s Your Favorite Movie of All Time?
A favorite movie can say a lot about a person! Whether they’re into Star Wars or Legally Blonde, knowing what they find entertaining gives you some true insight into who they are as a person.
#12 What Is Your Dream Job?
How does their dream job compare to their current job? Do they like working? Do they feel fulfilled in their role or are they looking to switch careers?
#13 What Does Your Perfect Weekend Look Like?
What does leisure time look like for your crush? Would they prefer to hit the beach or cuddle up with a good book?
Do they like spending lots of time with friends and family or do they find it more fun to hang out alone?
#14 What Was Your Favorite Thing to Do as a Kid?
What made life memorable for them when they were younger? What toys did they like to play with? Were they in any organized sports, clubs, or recreational hobbies?
#15 What’s the Silliest Thing to Happen to You Recently?
When was the last time they laughed really hard? What, in general, makes them crack up? Do they value a sense of humor?
More Serious Questions to Ask Over Text
At some point, it’s important to transition from casual conversation starters to more serious, relationship-based questions.
Once you’ve broken the ice, it may be time to heighten your text conversation. This is especially true when you really like someone.
Here are some questions to consider asking:
#16 What’s the Most Embarrassing Thing That’s Ever Happened to You?
Maybe you already know the funniest thing that’s happened to them? But what about the worst thing? The one that still makes them cringe or feel guilty?
This question can better help you understand your crush and recognize their fears and perceived weaknesses.
#17 What Have You Read Recently That Really Impacted You?
Does your crush like to read? Having a conversation about books may be the way to their heart- bonus points if you’ve read the same thing!
#18 What’s the Best Advice You’ve Ever Received From Someone Else?
It’s a good idea to know what inspires your crush. What’s made them a better person?
What are their values in life? This broad question can help you better define those answers.
#19 What’s the Most Important Thing I Should Know About You?
This is one of the best open-ended questions you can ask someone. It’s a surefire way to keep the conversation going.
#20 How Do You Relieve Stress?
Are they into exercising or meditating? Do they constantly feel stressed, or are they generally more mellow and go with the flow?
#21 Do You Have a Role Model?
Who inspires them to be a better person? What kind of values do they look for in other people? And do they believe they’re a role model for someone else?
#22 How Do You Feel About Your Friends?
Are they more introverted or extroverted? Do they feel like they get along well with others? Do they talk to their friends on a regular basis- or is it more erratic?
#23 What Personality Type Are You Most Attracted To?
This is also one of those interesting questions to ask where the answer may totally surprise you!
#24 What’s the Most Romantic Thing Someone Has Ever Done for You?
Even though you might feel nervous discussing ex-relationships, your fears may be irrational.
Learning about what worked for them in the past can help you strategize how you will keep them happy moving forward!
#25 What Do You Value the Most in a Relationship?
It doesn’t take a relationship expert to know that it’s important to understand someone else’s preferences in a relationship.
Does your crush love someone with a good sense of humor? Or do they want someone who’s deep and serious?
#26 Who Knows You The Best?
There’s something so personal about this question. Is your crush more of an open book, or are they more reserved with their secrets?
Do they feel super close to their mom or their best friend or their therapist? You won’t know until you ask.
#27 How Important Is Family to You?
Does your crush consider family the most important thing in life? Or are they more distant from their relatives?
Are there relational problems you should know about? And if so, how much do they impact your crush’s emotional well-being?
#28 What Do Most People Misunderstand About You?
What is your crush tired of explaining to other people? Do they often feel like nobody gets them? Are they frustrated with feeling lonely around others?
This is one of those deep questions that can help you understand their pain points- knowing this can help you tap into more empathy when you talk to them.
#29 What Do You Value Most in Life?
Shared values are so important in a relationship. While you may not agree on everything, it’s important to have some common goals that keep you together.
Whether it’s family, love, school, or building a business, knowing how your crush structures your time will give you a good idea as to what to expect if you get into a relationship with one another.
#30 What’s Something You Really Hope Comes True in Your Lifetime?
What are their deepest hopes and aspirations? Do they want to have children? Travel the world?
Live in a great house? Knowing this answer will help you better understand their main priorities in life.
#31 What Instantly Turns You off When You’re Talking to a Guy?
Does your crush hate when a guy wants to spend money frivolously? Or when he’s rude to the waitstaff? Does she get upset when he will only talk about himself?
#32 What One Word Best Describes Who You Are as a Person?
This is a challenging question, and it’ll force someone to really think about the one thing that makes them stand out as a person.
#33 What’s the Most Interesting Thing About Me?
Similar to the above question, it forces someone to really narrow down their options to describe someone.
#34 What Three Words Would You Use to Describe Me?
There are so many ways to answer this question, aren’t there?
But one thing is for sure- you’re probably very curious to know their answer!
#35 Who Has a Better Sense of Humor? You or Me?
Is your crush going to be flirty, honest, or both?
#36 What Do You Make Of Our Conversations?
Are you just some guy she sees as a friend? Or does she really look forward to your interactions? You have to ask if you want to find out!
#37 If We Had to Spend Time Together Right Now, What Would You Want to Do?
This answer will give you an idea of how your crush wants to have fun with someone else. Will they respond with a wholesome answer?
Or will they be more flirtatious? Either way, there’s a good chance that their response will make you blush.
#38 Do You Have Any Idea How Much I Like Talking to You?
Sweet, flirty, and to the point. This is one of the cutest questions to ask when you’re just starting to flirt with someone.
#39 When Am I Seeing You in Real Life?
Will it be tonight? Tomorrow? Sometime next week? If you don’t ask, you’ll never know!
#40 What Was Your First Impression of Me?
If you’ve met in person, this answer will give you a good idea of how your crush perceived you. Hopefully, all went well!
#41 Is It Just Me or Do You Also Wish We Were Together Right Now?
This is a flirty question that also has sweet, romantic undertones. It puts the ball in your crush’s court to talk about how much they miss you, too!
If your crush says that they wish you were together, consider being bold! Ask them if they want to hang out right now!
#42 Can I Talk to You on the Phone Right Now?
Sometimes, conversations over text become mundane. You can only share your favorite meme, or send a bunch of emojis so many times.
The phone (or Facetime) makes things far more personal, especially if you’re stuck on taking things to the next level. Just be prepared for a more intimate conversation!
Other Text Conversation Starters (That Aren’t Questions)
Anyone who’s been on dating apps knows that questions start to sound the same after a while. Even if you have good chemistry with someone, don’t get sloppy in how you talk to them.
When it comes to texting, the most important thing is to stay fresh and interesting.
Here are some ideas:
#43 Talk About a Major Recent Event: Whether it’s the latest election or a celebrity scandal, there’s probably some chance your crush is aware of it!
Talking about current events is an easy way to keep the conversation going, and it can give you an idea as to what kind of news they follow in their free time.
#44 Talk About the Last Time You Hung Out: What did you do last time you were together? How did spending time with your crush make you feel?
You don’t have to overcomplicate this kind of message or dive into all the details. It can be as simple as saying, I honestly had so much fun last night.
#45 Talk About the Weather (Jokingly): It’s a cliche for a reason! But you can make fun of the cliche together by saying something like, It’s so hot today. Wow, I can’t believe I’m talking about the weather with you!
#46 Talk About a Mutual Interest or Person: If you two met through someone, that’s an easy conversation point. You can talk about your relationship with that person.
And if you met through work, school, or a shared hobby, that’s an automatic discussion topic! Just make sure that you don’t fall into the habit of only talking about that shared experience.
You want to get to know your crush outside of that box.
#47 Talk About Something Interesting That Just Happened to You: There’s nothing wrong with asking your crush lots of good questions about their life.
But it shouldn’t be so one-sided that you don’t reveal anything about yourself. Show off what makes you unique or what makes your life different from everyone else’s.
#48 Talk About Future Plans: If you two have made a plan to see each other, talk about what you’re going to do!
It’s also nice to say something like, I’m really looking forward to Sunday! Is 6:00 pm still a good time for me to pick you up?
It’s important to prioritize having a meaningful text conversation with your crush. You want them intrigued and motivated to keep talking to you! In addition, you ideally want them to want to keep things going in real life!
Remember that the best conversation starters are genuine. Don’t talk about things that feel trivial or meaningless to you.
But keep in mind that if they like you, they will want to talk to you. They will keep finding reasons to text back- time and time again!