How To Start A Conversation With Your Crush Through Text – 21 Ways

July 13, 2023 |
Updated On: July 13, 2023
how to start a conversation with your crush through text
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Don’t know how to start a conversation with your crush through text? Do you know how the Office actor John Krasinski asked actor Emily Blunt out? He shook her hand and went straight to, “I like you”. Cut to the present, they are married and have two children.

Personally, chatting with my crush has never been easy for me. I hide behind a screen and wait for his reply. Do you relate? It is time for you to become their favorite notification. Here’s how.

How To Start A Conversation With Your Crush Through Text – 21 Ways

Are you afraid of asking your crush out in person? Don’t worry, even research says that texting your crush can be beneficial to you in the following ways:

  • You have time to carefully consider what you wish to say
  • Less damage is done to your self-esteem in case you get rejected 

So, a text conversation is way safer. But texting someone new is not that easy, right? How does one sound sweet without sounding cringey? How to not be a dry texter? Watch and learn. Here are some ideas that can be your game changer:  

1. “Netflix? Chill? Both?”

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. So, take a deep breath and get the ball rolling.

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2. “I’m craving sushi. Let’s go grab some?”

Instead of starting with a simple hello, tempt your crush with a shared interest. 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?”
  • “There’s something brewing between us. So, how about a beer?”
  • “We should get coffee sometime, I like you a latte!”

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

3. “Did you watch the last episode of Manifest? The cliffhanger won’t let me sleep!”

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 be friends with your crush, bonding over cinema can help you. Everybody loves giving an opinion on stuff. 

4. “Love your outfit. Where is it from?”

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

  • “Love those Air Jordans”
  • “Oh! You’re a Liverpool fan too?”
  • “Hey, is that Van Gogh exhibition worth the hype?”

5. “Pineapple on pizza? Yes or no?”

This is just to remind you that even a basic question like this can spark a lengthy conversation. Maybe keep a photo of the pizza you ate yesterday ready as well. 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, keep the flow of the conversation going. Don’t just use romantic texting as an excuse to flex your game.” 

6. “I suck at starting conversations, you wanna try?”

Sometimes 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 are some leading questions for you to send in their DMs:

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

  • “I’m terrible at small talk, but I make a killer playlist”
  • “Can I have your number so that I can 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”

7. “What’s your story?”

Be forward and ask your crush about their life. The highlight of their week. Their side hustle. The lowest point of their day. A Reddit user’s advice on what to text your crush at night, “Just talk to them like you’re talking to a friend. Don’t be creepy or ask for nudes. Just joke with him/her and talk when you absolutely have the time.”

8. “I had a dream about you last night. I’d tell you about it but it’s super inappropriate”

Your first text on a dating app has to be something unique, instead of a simple ‘Hey.’ If you’re in the mood to be bold and gutsy, use these flirty texts to turn your love life around:

  • “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”

9. “Sasuke or Naruto?”

Model Barbara Palvin had 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, on common interests like anime.

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10. “You keep bumping into me. Not that I’m complaining”

Asking your crush about your last encounter can be one of the best ice breakers 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! Love 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?”

11. “Hey stranger, wait, why are we strangers? Let’s fix that”

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.

12. “We are both single! Let’s solve this together”

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.

13. “Serious issue: Can’t stop thinking about you”

There is no dearth of research on how a slightly risqué joke can help to escalate the level of intimacy in a flirtatious conversation. So, make judicious use of humor to start the convo. You can also use the classic ‘knock knock’ joke:

You: “Knock, knock”

Crush: “Who’s there?”

You: “Wire”

Crush: “Wire who?”

You: “Wire you still not in my phone’s favorites list?”

14. “Tea, coffee, or whiskey in the morning?”

And don’t forget to add cute smileys. 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.” You can also send your crush an ice cream GIF saying, ‘Lick me’.

15. “Should I delete my Tinder app already? I think you’re the one!”

Cheeky, isn’t it? Wait, we have more for you. Kick-start a conversation with your crush with these cheesy pick-up lines:

  • “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?”

16. “You could text me back or just ask me out to dinner. Just saying”

Smooth, isn’t it? But, as a Reddit user pointed 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?”

17. “Wanna suffer together?”

If you are still trying to figure out how to start a conversation with your crush through text, just send the ‘Wanna suffer together?’ meme. Even a Reddit user advised, “Memes are the way of the future”. And where’s the lie? Cute SpongeBob memes can be your savior. That’s how Gen-Z uses memes to flirt.

18. “Can you try me? Try me? Once you put your pride aside

Yes, now is the time to send a Weeknd song. You can also send Starboy or Earned It. Sending music is a love language. As a famous dialogue from the movie Begin Again goes: “You can tell a lot about a person from what’s on their playlist.”

Related Reading: The 5 Types Of Love Languages And How To Use Them For Happy Relationships

19. “My place or yours? JK, my parents are home”

Instead of starting with a simple hello, you can use a self-deprecating line like, “I hope you like bad guys because I’m bad at pretty much everything.” The trick is to be funny, without overdoing it. A Reddit user wrote, “Self-deprecation is fine in small doses, but it gets old fast and can seem like nervous energy very easily, so keep it casual and contextually appropriate.” 

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20. “You’re hotter than the bottom of my laptop”

Throwing in wonderful compliments to make them happy can be a great way to start a conversation. “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 kissass like that. Do it from time to time when the moment calls for it, and be gentle about it when you do.”

21. “I’m obsessed with your puppy”

Ask them their dog’s name. Or tell them about your cat. It’s always endearing to bond over pets. If your crush replies with enthusiasm, you can thank us later. 

Key Pointers

  • Starting a text conversation with your crush means using the right amount of humor and wit
  • Don’t jump straight to the dating topic, you can try to be friends first
  • Forward a funny video to break the ice
  • Don’t keep waiting for the answer; just go do something else
  • Another example of conversation starter is to ask details about their day
  • You can also ask other things like their pet’s name or what they’re up to on the weekend
  • Don’t try too hard when texting someone new; just be yourself and keep it light

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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