What To Text Your Crush: Tips And Ideas To Start A Conversation 

Single Life | | , Researcher & Content Writer
Updated On: March 11, 2024
how to start a conversation with your crush through text
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Do you experience butterflies in your thumbs (yes, that’s a thing) every time you think of what to text your crush? Think about it like the butterflies in your stomach when you get a chance to talk to your crush. That’s kind of what I would experience in my fingers every time I needed to text the guy I admired and wanted. Well, whatever I put down in those texts worked because we did end up together for 3 glorious years.

So, if you, too, struggle to find the right words to text your crush, I’ve got you covered. Drawing on my experience, I will share some tips and ideas on what to talk about with your crush over text. And if they work, make sure you let me know.

What To Talk About With Your Crush Over Text: 15 Tips And Ideas

Are you afraid to ask your crush out in person? Well, the truth is even texting can be pretty tough. Any words you put into that text carry so much meaning. You want to convey whatever you need to without looking desperate or needy. Also, how does one sound sweet without sounding cringey? You also don’t want to be a dry texter because you need to hook them from the first words. Surely, finding the right words to text a crush can be a tightrope to walk. To make sure you don’t fall off the wayside, I have some pretty amazing tips and ideas on what to talk about with your crush over text.

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1. Start with a simple greeting

The simplest way to kickstart a conversation with your crush is with a greeting. Ok, maybe I am simplifying things a bit too much. After all, you can’t just text hello and nothing more, right? What if they don’t respond and now you are left biting your nails wondering if the phone service providers shut down your line? It’s important to be a bit creative and impressive about how you text your crush with that first text. So, try the following text conversations.

  • Friendly vibe: Hey Bob, Just wanted to say hi and find out how your day is going.
  • Engaging: Hi there. How is the day going? Hope things are going well for you
  • Flirty: Hey you, I thought you needed a brightener to your day, so hello and have a nice day
  • Warm: Hey Bob, how is your day shaping up? Sending plenty of positive vibes your way.

Remember, when thinking about what to talk about with your crush over text, you need to check their level of interest. If they respond to a simple hello, it shows they are willing to engage with you and start talking. After that, you can elevate the text conversation with humor, jokes, or more probing questions.

2. Be bold in your approach

How to text your crush without being boring is by saying what you need to. If you can’t decide on what to text your crush at night, go with the classic ‘Netflix and chill’ line. Yes, we know it’s pretty direct. But sometimes, being bold can work for you. Take a deep breath and get the ball rolling. So, try the following if looking for what to text crush at night.

  • Hey Bob, feeling cozy tonight? How about we indulge in some Netflix and chill
  • Hey you! Netflix and chill tonight? I will bring the snacks
  • Feeling bored and nothing in the works? How about some Netflix and chill?
  • Hey, want to indulge in some bingeworthy experiences. I have some great Netflix and chill ideas. 

Admittedly, this approach is not for the fainthearted. If your crush says no, it can be a major bummer. That is why you may want to hold off on this idea until you know your crush a bit better. At least, you will have the benefit of knowing what they like or don’t.

3. Explore your flirty side

texting someone new
Texting your crush should be fun and flirty

“I want to chat with my crush but I am afraid he will find me boring.” If that sounds relatable, figuring out how to text your crush without being boring may require you to be a bit flirty. If you’re in the mood to be bold and gutsy, use these flirty texts to turn your love life around:

  • “I had a dream about you last night. I’d tell you about it but it’s super inappropriate” (you can be sure this will capture your crush’s interest immediately)
  • “My computer server never goes down, but I do”
  • “Are those space pants? Because that ass is outta this world”
  • “Let’s skip the small talk and go straight to flirting”

A flirty message or flirty dares over text are excellent examples of what to text crush at night. You can be sure they will be thinking about you in the night. Don’t be surprised to wake up to an equally naughty message in the morning. Now, it will be your turn to have a silly smile on your face the whole day.

Related Reading: 35 Beautiful Goodnight Messages To Text Your Crush at Night

4. Tempt your crush with a shared interest 

How do I start a conversation with my crush? Well, you can draw your crush into a conversation by talking about a shared interest, passion, or goal. It is a great way to start a conversation and eventually ask your crush out. So, if they are a foodie, here are some fun ways to kick-start a conversation with your crush (puns can never go wrong):

  • “Do you have raisins? How about a date?”
  • “I’m craving sushi. Let’s go grab some?”
  • “Something is brewing between us. How about we find out more over a beer?”
  • “We should get coffee sometime, I like you a latte!”

Asking your crush to do something they like with you is a sure way to get them interested. The best part is that once you find common ground, you’ll likely have a great time in each other’s company.

5. Talk about your favorite show

Wondering what to text your crush? A great way to start a conversation would be to talk about your favorite show. And find out theirs too. It could be Friends or Sex Education. Or evergreen movies like Fight Club or the Before trilogy. If you want to get your crush to like you, bonding over cinema can help you. Everybody loves giving an opinion on stuff. Here are some texts that are sure to get you a response.

  • I have been binge-watching Rookies, have you seen it?
  • Did you watch the last episode of Manifest? The cliffhanger won’t let me sleep!
  • What did you think of the latest Blacklist season? The plot lines are really thickening
  • What is that one series you can rewatch a hundred times? My favorite is Criminal Minds

6. Show interest in their lives

How to get your crush to like you? Just reply to their Instagram story. The most important thing is to show an interest in their life. You don’t even have to pretend; we know you’re genuinely interested. Here are some great conversation starters:

  • Love those Air Jordans
  • Oh! Are you a Liverpool fan too?
  • Hey, is that Van Gogh exhibition worth the hype?
  • Love your outfit. Where is it from?

You can build up on this by asking your crush more about their life. A Reddit user’s advice on what to text your crush at night is, “Just talk to them like you’re talking to a friend. Don’t be creepy or ask for nudes. Just joke with them and talk when you absolutely have the time.”

7. Keep it basic when texting your crush

How do I start a conversation with my crush? Don’t overthink it. The answer to what to text your crush can be as basic as: “Pineapple on pizza? Yes or no?” This can spark a lengthy conversation or even a spirited discussion.

A Reddit user wrote, “Flirtation is good but remember there’s another person on the other end of the phone. Ask normal questions too, seem interested, and keep the flow of the conversation going. Don’t just use romantic texting as an excuse to flex your game.”  Try the following conversation starters.

  • Hey, any plans for the weekend?
  • What’s your favorite relaxation technique?
  • Finally got to watch the movie you mentioned. Anything else that is as good?
  • Hey just checking up on you. Is anything interesting happening in your life?

Related Reading: Platonic Crush — Meaning, Signs, And What To Do

8. Kill the awkwardness from the beginning

how to text your crush without being boring
Bring out your fun side when texting your crush

How to open a conversation with your crush may require some creativity. For instance, the best way to kill the awkwardness is to talk about the awkwardness. Being explicit about implicit things can make them laugh. If you/your crush is an introvert, here are some leading questions to kickstart a conversation with your crush:

  • I suck at starting conversations, you want to try?
  • I’m terrible at small talk, but I make a killer playlist
  • Will you think I’m weird if I just text you but literally never call?
  • Hey girl, want to party with me? It’s not really a party. It’s actually a book club, and there’s a cat

Model Barbara Palvin shared glimpses of chats with her boyfriend, Dylan Sprouse. Dylan had asked her, “You more of a Sasuke gal or Naruto gal?” Barbara chose Naruto because he was “a little damaged boy with a strong passion who loves food”. This is when Dylan called her a “real keeper”. So, stop thinking and go chat with your crush without being awkward about common interests like anime.

9. Talk about your last encounter

Talking to your crush about your last encounter can be one of the best ice-breaker questions for dating. Here are some cool ideas to get the conversation flowing:

  • What’s your biggest regret? Mine is not kissing you last night
  • Lunch was fun! I loved sitting across from you. When are we doing it again?
  • You see how I look at you. What are you going to do about it?
  • You keep bumping into me. Not that I’m complaining

Talking about the last encounter is an excellent way to show genuine interest in pursuing things further. Text conversations also let you express yourself without having to say the words out loud. Also, if you want to know what your crush thinks, using open-ended questions is a great way to get them talking. 

10. Bring some humor into the conversation

How to talk to your crush without being awkward? Bring out that witty personality of yours! Want to sound smart? You can ask, “On a scale of America to 10, how free are you tonight?” This will reveal your political awareness as well as make your crush laugh. Here are some other ideas you work with to make your crush chuckle:

  • Hey stranger, wait, why are we strangers? Let’s fix that
  • We are both single! Let’s solve this together
  • Hey! Just wondering, on a scale from one to ‘I can do whatever I want’, how booked are you tonight? Let’s see if we can squeeze in some hangout time!
Does My Crush Like Me

The key to figuring out how to open a conversation with your crush is to not approach it with too much seriousness. Don’t be afraid to show your humorous and slightly naughty side. After all, you’re texting your crush and not your friend. So there’s no harm in making it obvious that you like them.

Even research says that women looking for short-term relationships are the most effective at flirting when they make their sexual availability known. So go on, tell them you’re tired of being single and so ready to mingle.

11. Be serious when you need to

“How can I write a message to my crush about my feelings?” Well, how about just doing it? Think about it, what is the worst that can happen? If your crush doesn’t respond the way you expected, that’s ok. That’s just one of the signs that they don’t like you back. You can stop wasting your time and pursue other interests.

If they do reciprocate, it could be the beginning of something beautiful. So, if you’re ready to rip the band-aid off, here are some ideas:

  • Hey, I really like you and just thought I would let you know. Fingers crossed that you feel the same, if not, I will totally understand
  • Hi! I want you to know that my feelings for you have grown tremendously. I hope you would be open to us exploring a deeper connection 
  • I hope I am not crossing the line by telling you how much I like you 
  • Would you like to go out on a date with me? I know I would love to spend some time with you

Related Reading: How Do Introverts Flirt? 10 Ways They Try To Get Your Attention

12. Throw in some compliments

Throwing in wonderful compliments to make them happy can be a fantastic ice-breaker.  “Your hair looks great” could be a good place to start. But as a Reddit user advised, “Don’t compliment them all the time, no one likes someone who’s a kiss ass like that. Do it from time to time when the moment calls for it, and be gentle about it when you do.” Here are some ideas:

  • You are hotter than the bottom of my laptop
  • God was in a good mood when he created you
  • Hey, quick question, is it me or do you look more amazing every time I see you
  • Your smile has the power of a thunderbolt to my heart

I reiterate, keep the compliments to a minimum so that they yield a positive reaction when you do use them. Use them too often and you will come across as trying too hard. In fact, after a short time, your crush may start thinking you are fake.

on crushes

13. Include some GIFS or emojis

How to start a conversation with your crush through text when you aren’t too good with words? Well, how about using GIFs or emojis? These animations remove the seriousness from the text conversations. They can also communicate a lot without you having to say anything. Guys also use emojis when they love you, so why shouldn’t you?

A Reddit user wrote, “I’ve learned emojis and now GIFs really help. They are fun and silly and get points across without seeming like a creep.” Here are some you can try your hand at to engage your crush:

  • A flirty wink is playful without being too over or offensive
  • A laughing emoji shows you appreciate your crush’s humor
  • Heart eyes convey admiration or affection
  • Cute animal GIFS can make your crush’s day brighter. Sending a dog emoji or GIF to your dog-loving crush, for instance, will win you some serious brownie points.

14. Bring out your fun side with cheesy lines

Cheesy lines are fantastic icebreakers and an excellent answer to what to text your crush to start a conversation. They can also help make light of a serious conversation. Kick-start a conversation with your crush with these cheesy pick-up lines:

  • Should I delete my Tinder app already? I think you’re the one!
  • I have a comfy, oversized hoodie just waiting for you to borrow
  • I’m down to 1% battery but I’m using it to text you
  • What would it take for you to drunk dial me?”

Now, remember, it’s important to use cheesy lines judiciously. This is especially true if you are texting someone new. Since you don’t know the person too well, these can come across as offensive. You may also come across as trying to be smooth which would backfire on you. 

A Reddit user points out, “Never try to be smooth. If you’re trying to be smooth or trying to look cool or trying to think of what to say, you’re forcing it and it’s making them uncomfortable because they can tell.” So, just be direct and say, “Chipotle tonight at 7, you down?” that sounds much better than “You could text me back or just ask me out to dinner. Just saying”.”

Related Reading: The 13 Best Tips For Dating In the Middle Age

15. Discuss dreams and aspirations

Maybe you don’t want to do this in the first text you send your crush. But, as you get to know each other more, talk about your dreams and aspirations. It doesn’t have to be anything super serious. You could also just try and find out what they like and build on that. Some ideas on what to ask your crush over text, which are also great conversation starters are:

  • My dream is to one day backpack across the world. What about you?
  • Do you have a bucket list? What is that one thing you will cross heaven and earth to complete?
  • I have always wanted to play the violin. Do you have an instrument you would like to learn?
  • What are you really passionate about?

Now you may be wondering, “How can I make this a message to my crush about my feelings?” Well, you can include yourself in the plans. For instance:

  • I have always wanted to learn a musical instrument but have always been afraid to sign up for classes alone. Is there an instrument you would be interested in so that we can sign up together?  It would be great having you there with me
  • I know you are passionate about helping the community. Maybe next time I can tag along to help out. It would be great to spend the time with you 

Key Pointers

  • What to text to your crush should contain the right amount of humor and wit
  • When thinking about what to text your crush to start a conversation, don’t jump straight to the dating topic, you can try to be friends first
  • What to ask your crush over text should be engaging so that they respond. Use humor and wit to bring out your personality and to break the ice
  • Don’t try too hard when texting someone new; just be yourself and keep it light
  • How to text your crush without being boring is to ask open-ended questions, show interest in their lives, or ask about what is important to them. In the text conversation, you can also ask other things like their pet’s name or what they’re up to on the weekend

The final tip on how to start a conversation with your crush through text is to avoid playing mind games. Actor Chris Pratt advised, “The truth is that any amount of trickery or wearing cool shirts with rad designs or using pick-up lines, or any of this BS like trying to neg girls, isn’t going to matter. It won’t pay off when she realizes that you’re full of sh*t.”

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