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How to Start a Conversation with Your Crush Through Text

You probably have that one crush you want so badly, but talking to them feels daunting. Initial conversations with crushes aren’t easy, but texting can help. This article helps you with how to start a conversation with your crush through text.

How to Start a Conversation with Your Crush Through Text

Starting a conversation with your crush can be challenging. Especially so, it’s somewhat difficult if you can’t tell the feeling is mutual. But there’s usually a way around it, and text messaging offers the perfect leeway.

But before I drift further, here’s a little about me.

I’m Frankie Caruso, an enthusiastic and seasoned messaging app expert, and I’ve had a few crushes before, just like you. But much to my dismay, one-on-one conversations haven’t worked so much for me in the past.

However, text messaging has been my secret weapon, forging conversations, engaging all my crushes, and keeping them intrigued. So, how about I share a few of these tips with you and nail your crush without effort? Or if you need more effective tips similar tips, you can subscribe to my newsletter.

Besides sending texts, you need to do it with a proper strategy.

Talking to a crush might not be a “make it or break it” thing, but it’s annoying if you don’t lure the person you admire into a conversation. But as usual, I’m here to help you get the birdie or guy in your line!

Here, I’ll help you with some killer tips to make talking to your crush a breeze. I’ve structured this article into four comprehensive parts, including

  1. Why text messaging is the most effective
  2. How to start a conversation with your crush using text messaging
  3. The various strategies to make your crush intrigued in your text messages
  4. The Frequently Asked Questions

So, let’s delve into it without further ado!


Frankie’s Take:

Getting your crush intrigued in your text conversations is as easy as ABC! However, it’d be best if you had a good clue about the killer convo strategies, which I’ll offer the nitty-gritty about. Going all in without a proper texting strategy can hurt your chances of starting a convo.

Why Text Messaging is the Most Effective for Talking to Your Crush

How to Start a Conversation with Your Crush Using Text Messaging

I love to commend text messaging for its simplicity and how seamlessly it forges communications. There’s usually no sense of space, and you can easily reach anyone without an effort.

Especially so, messaging makes winning over your crush easier than you would when you did it physically. You don’t have to torture yourself with fidgeting and racking your brains to say that perfect pickup line you’ve been nervously rehearsing over and over.

Text messaging helps you communicate outrightly and without worrying about making the wrong impression on your crush.

Besides, you don’t have to sweat about how their reaction would be hearing your voice break or making weird poses to cover your shyness.

But how do you use text messaging to initiate the first tough conversations?

Please note: You must choose your words correctly when starting a conversation with your crush. Just saying “Hi” is bland and makes you come through as clueless. But don’t worry, we’ll sort that out.

How to Start a Conversation with Your Crush Using Text Messaging

You have to admit that starting a conversation with your crush isn’t easy. Moreover, it gets a bit trickier if you’re introverted and can’t muster the courage to say your first word, “HI.” So how do you start the conversation in the first place? Below are the best tips you can use to initiate that tense convo.

Ask a Leading Question

A lending question usually initiates a conversation better than starting with a simple “Hello.” But which question intrigues them better, and how do you coin it? Easy-peasy!

Of course, it’s only a crush you have for each other – or perhaps, you alone. Fairly enough, you hardly know anything about each other. So, how about doing a little digging to understand what your crush is interested in?

There’s always something that everyone would like profoundly, that’s for sure.

If you both share a liking for football, you could ask them about their favorite sports team or last week’s score. Or, perhaps, it could be about one of last night’s band performances in one of the town’s popular joints. Please be sure they can comfortably answer whichever leading question you ask.

Say Something Sweet

Your mind could suddenly go blank if you were to say anything sweet to your crush in their face. (I get it; I’ve been there before). However, we all have text messaging to thank for.

The good thing is that texting allows you to think over what you need to say. It gives the buffer you so much need.

But what’s the sweetest thing you could tell your crush?

They already know they’re pretty and won’t need reminding with a “Hey, you’re pretty” phrase. So, how about a little wit in your statements?

Please don’t go telling them their smile could wake the dead; that’s way scary – who fancies waking the dead, anyway?

Instead, saying, “your smile is radiant. I could use it on my gloomy days,” sounds flirty and lets them know they’re pretty without telling them they are.

Don’t worry about your crush failing to revert after your flattering text. Trust me, they’ll at least smile, and you’ll make their day.

Jog their Memory a Bit

I love this trick, and it works pretty fine.

However, you should know a few things about them before you find a proper ground.

Let’s say you’re past the first-time “Hi” and “Hello” pleasantries and interacted a bit. You can use what you talked about earlier and start a conversation.

If perhaps, you had a convo about your shared love for some cute huskies, you might jog their memory on the same. “What’s the name of the doggy shade you told me about, again?” could be perfect to start a conversation.

You can ask virtually anything that sparks enthusiasm, but please do it when they’re least caught up with whatever they’re doing. Pretty sure you’ll steal a conversation there.

Start With an Emoji

I’m not talking about those angry or spear and arrow emojis. (I mean, why would you even send such emojis to your crush to win them over?) Trust me, they won’t revert, and you’ll be left staring at your phone, waiting for a reply.

Instead, I’m talking about the sweet and flirty emojis. However, you could reinforce the emojis with a dallying text, fixing them at the end.

Something like, “You killed it with your dance moves yesterday. Did Michael Jackson learn from you? 😉”

Trust me, it’ll flatter them, big time. Besides, it’s coy and not way overboard. If they don’t reply, stay patient; they sure will.

Be Marginally Curious, but please be Genuine

Here’s some perspective: you’d be genuinely flattered and take a keen interest in anyone who notices you. More so, you crush? That’d feel surreal. You’d get your fingers typing a reply back if the feeling is mutual.

So, how about doing it to your crush? I’m sure they’ll feel the same and will reply instantly.


Frankie’s Take:

I like to think that crushes are incredibly delicate, and every word you tell them reveals your personality to them. More so, it’s more challenging if they haven’t taken note of you yet. Whether or not you’ve interacted before, thoughtfully choosing your words helps.

The Various Text Messaging Strategies that Keep them Interested On End

Text Messaging Strategies that Keep them Interested On End

Besides starting a conversation with your crush, you must fuel them and make them interesting. I’ll tell you what I’ve observed with most of my crushes.

It’s relatively easy to keep a crush intrigued if you share a mutual feeling.

However, it takes a proper strategy to charm one you’re trying to pin down if your crush marginally has a crush on you – or not. So, here’s how to keep the fire inside them burning on end and interest them in every word you say.

Follow up With an Open-Ended Question

Your first line may be successful, and you may get that reply. But how do you keep the conversation going?

I usually prefer using open-ended questions to fuel the conversation. A question they can relate to and doesn’t only warrant a “Yes” or “No” is ideal.

It offers you leeway for a hearty conversation with your crush, and you’ll find ground in your exchanges.

Keep them Noticing You at Least Once a Day

Letting your crush recognize your presence and that you exist them interested. However, one mistake I see people making is bombarding them with a thousand words (literally) daily. That compromises your strategy.

Instead, it’s always best to text them once a day or maybe every other day. Make sure they notice your presence and know you’re still around.

Avoid being a clingy texter since that makes you seem desperately needing their attention. Being too available can hurt your chances of winning them over. Trust me; no one loves an overly clingy person.

Ask Them about How their Day Panned Out

A little concern can go a long way, and asking your crush about their day can bolster your chances of keeping them around.

Your first text might have won them over, but it takes a little concern about what’s going on in their little world to let them know you’re interested.

You never know what they’re willing to tell you. It could, perhaps, create one of those fine days you text late into the night.

However, it’d help if you sounded genuine, wanting to know more about what has been going on in your absence. Keep keen, and listen to what your crush has to say.

Complement them a Bit

Please don’t condescend, and I really stress that. Your compliments should only show appreciation for doing something good or right, but not too overboard to flatter them.

If you’re hitting it off at this point, they’ll probably be open to telling you about their day’s achievements and their little wins. A slight “Wow, you’re really clever” for finally finding a solution to a problem they told you about earlier can sound genuine and less condescending.


Frankie’s Take:

It’d be best if you didn’t stoop low with excess praise in your compliments; it sounds so desperate. Maybe that’s how I feel, but I guess you get my idea.

Frequently Asked Questions about Starting a Conversation with Your Crush

I’ve had a few people privately asking questions about making the first conversations with crushes successful. I’ve therefore detailed the most popular and frequently asked questions below.

How Do I Know if My Crush Likes Me by Text?

Telling if your crush likes you is relatively easy. They’ll usually respond quickly and reciprocate the energy. Also, most crushes will appear flirty and generally interested, and they’ll laugh at anything funny you tell them.

How Do I Keep my Crush Interested?

You can do a lot to keep your crush interested, including being bold in your conversations, complimenting them slightly, and showing interest back. You can also let them know you’re available, but ensure they’re aware of your schedule.

What Should I Not Text my Crush?

You can text your crush about anything that excites them, but avoid R-rated words, overdoing the words and emojis, or playing mind games with them. That instantly flips them over and can be an instant turn-off.

How do I Text a Flirty Text to my Crush?

Pretty much anything that sparks interest or puts a smile on your crush’s face is ideal. Phrases like, “I’ve been looking for the dictionary that defines your beauty in vain,” or “Wow, you look like a lot of fun” sound flirty, and they’ll revert.

When do I Text my Crush that I Want Them to be my Boyfriend/Girlfriend?

Before asking your crush to be your boyfriend or girlfriend, you need to ask yourself if they like you or are attracted to you or not. You can easily tell that by how you hit it off, including how they text you back, the energy, and the vibe. If that checks out, you can shoot your shot.


Before I wind up this article, I would like to affirm that texting your crush and keeping them interested for as long as you want is easy.

However, it helps to have a proper strategy to make it successful. To help you out, here’s a summary of what you need to do to start a conversation with your crush.

  • Ask a leading question
  • Say something sweet
  • Jog their memory a bit
  • Start with an emoji
  • Be marginally curious, but be genuine

Besides, it’d be best if you kept them interested on-end, and here’s what you should do:

  • Follow up with an open-ended question
  • Keep them noticing you at least once a day
  • Ask them about how their day panned out
  • Complement them a bit

But before we go, you might find these tips on texting a girl and how to impress guys on WhatsApp chats incredibly helpful.

These tips should give you confidence behind your phone’s screen, and you’ll win over the birdie or guy you admire through text.

As always, a hug,

Frankie Caruso

PS – If you’d like to learn more about killer text messaging tips, please subscribe to my newsletter and follow me on Facebook, or other messaging apps. You’re in for a treat, and you’ll gain valuable insight.

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About Frankie Caruso

I'm Frankie Caruso. I'm a professional amateur in that ugly business of social media, instant messaging apps and computer security. I help all those frustrated people who call themselves digital illiterates to understand something about this confusing digital world.

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