How to Start a Conversation Over Text With Your Crush

By on November 12, 2015

Let’s look at how to start a conversation with your crush over text and keep it going. First of all let’s look at how to get your crush’s number though as that’s the starting point!

Getting His Number

The best way to get a guy’s number? Have him ask for yours. Sometimes men are bit daft  (as they say in Britain) though and don’t get round to it. You may have to help him along.

If you’re chatting to him about something, tell him you have to go now, but he can text you about whatever he’s talking about later. “That’s so cool you like x, y, z too. I’d love to find out what you think about x. I gotta go now, but text me later.” This should make him ask for your number. If not, just go as you said you would and say something like “Cool, catch you later.” If he forgot that he hasn’t got your number, he will ask for it later. A man who wants to see a girl will do almost anything. The only time you should volunteer to tell you he doesn’t is if you’re not part of the same social circles and there’s no way for him to find your number.

If you are talking about a party or event for example and discussing whether you’re both going or not, tell him you haven’t made up your mind, but you can text him when you know. He should offer you his number at this point. If not, ask him if you have his number if he’s already agreed to you texting him: “I’m not sure yet. I’ll shoot you a text when I know, if you want?” “Sure, that’d be great.” “Cool. By the way, do I have your number?”

The above scenario can also happen the other way around: “Cool, let me know if you’re going, send me a text or something.” This should prompt him to ask for your number. Which is better than if you ask for his. If he just says “sure,” but doesn’t ask for your number, play dumb and just say “cool, see you later” and walk off. You shouldn’t have to beg for it.

If he asks you a question, like what you have to study for math class, or whatever, tell him you can’t remember and have to go now, but you’ll text him once you’ve checked your notes. Make to leave, then, as an afterthought, tell him you don’t think you have his number.

If he says outright you guys should hang out some time then volunteer your number.

If there’s a flirty vibe to the conversation, tell him when you give him your number that he better not misuse it! Or if he asks you for it say, “Sure, but only if you promise you won’t misuse it. Not anyone gets my number.” This only works if you guys are flirting though, or you’ll come across as an idiot. The reason why you say it? Men like challenges and men like feeling special.

How to Start Texting Him

If you’ve already talked about why you are exchanging numbers, then send him a text about whatever it was you agreed to text about. Add something fun to it, like a witty remark: “Hey, what’s up? Finally figured out what the maths homework was about – we have to do the exercises on pp. 22-24. I totally wanna borrow some brain cells from Einstein right now… Zara”


The important thing is you add something he can catch onto and have a banter with you about. You could crack a joke about the teacher, or the work…just something more than “This is our homework.” Or, “This is the link to the song I think you should check out the lyrics for.” Rather say something like “This is the link to the song I think you should check out the lyrics for. What do you think about it? Your kinda tune or not?”

Another great excuse to text someone is because you saw something that reminded you of them. Like if they said something really funny in class and then you are reminded about it later, you can text them. “Hey, what’s up? I just walked by a big sign for McDonalds and totally cracked up as it reminded me of what you said today! LOL”

If you’ve already texted a few times you can try things like:

“I’m so bored with Mrs Z’s homework right now. I bet you $5 she’ll even forget to check it tomorrow. She’s such a ditz.”

“So what do you think the odds are of us getting no homework tomorrow so we can hang by the beach instead?”

“OMG I was dying in class today – I was laughing so hard at Mr B’s wig I almost fell off my chair…I bet you $5 it will fall off before end of term…”

“You have to help me out here! Lisa said we have x homework, Sarah y and Paula z. What’s the deal? I’ve been sick for two days and my friends are totally lost and I know Miss R will totally kill me if I don’t hand in this assignment!”

Texts to Send if You KNOW There’s Chemistry

Already know he’s into you, or at least that you’re friends? Then you can be a bit more flirtatious, or personal, when you start a conversation over text.

“Help! Homework is a total drag today. Please distract me…”

“It’s so hot I can’t think. I feel like throwing my clothes off and jump in the pool. What do you think – pool or homework?”

“Stop making me think about you. I’m BUSY! :p”

“So I bet you wouldn’t dare see X horror movie with me? All my other friends are totally bailing on me. Cowards…”

“I can’t sleep. Wanna distract me for a while?”

“So I need to describe myself in three sentences for this thing I’m doing. Help me out?” (His cue to give you compliments.)

“Save me! I’m babysitting my eight year old cousin Dylan…he’s totally hyper and I don’t know what boys that age like. You’re a guy…help me out here!”

What NOT to Do

If someone you are texting never asks you questions and replies with short, curt answers, chances are they aren’t interested. Or simply they can’t talk then and there. So give them a break.

Don’t always answer straight away, unless you are having a conversation over text. When you get the first message, or a random message or two during the day, take your time. You have a life. If you drop everything to write a reply he will think you don’t have a life. And he won’t like it.

Don’t always let him end the conversation. If the conversation starts slowing down, say you have to go now. And even if the conversation isn’t slowing down, sometimes tell him you have other things to do right now, because you do. It will make him work harder for you because he will know you have a life and he won’t take you for granted. You have to put down boundaries from the start or he’ll think you aren’t taking your time to determine whether he’s worth it. Guys like to prove themselves. Let him.

What to DO

Do compliment him from time to time. In the beginning you can say things that refer to his personality like “You have such good opinions” or “You are definitively smart.” Or simply say you like his essay in school, or whatever. Further down the line things like “Your jeans were totally hot today” or “Guys who play rugby are totally hot” or “You shouldn’t wear a suit. I seriously can’t think straight when you do. Too hot.”

Everyone likes to feel good, so make him feel good! Don’t compliment him every day, but  do it ever so often. The better he feels around you, the more he wants to be with you (or text you).

Challenge him too. If he asks you out say yes, on the condition that he behaves himself, or shows you a good time. Make him think he really has to work for it. And let’s face it: he does. You don’t wanna date someone who bores you or treats you bad. Make sure it comes across as flirtatious rather than bossy though!

If he says “So, I really wanna see the new Bond movie tonight. Wanna come with me and grab some food before the movie?” you can can say “It depends… If you take me to a real cool place for dinner and you promise to make me laugh, I’ll come with you…” or “It depends – will you look as good as Bond tonight?” That should make him want to live up to your expectations (and being compared to Bond makes most men feel good…).

Ask him questions to keep conversations going, but don’t ONLY ask questions. Challenges are good, so are jokes.

In general when talking to a crush, or anyone else for that matter, turn your quirks into something good.

“Yeah, I confess – I’m a sucker for romantic comedies. See it as a bonus – I totally know how to avoid all cheesy situations in life. I know them by heart :p”

“Yeah, total nerd. I love maths. But smart people are better kissers according to geeky statistics, so I win. I’m just hot ;)”

“Sorry if my family was OTT tonight. They’re insane. Good thing is they taught me how to handle any kind of embarrassment. I have absolutely no fear of making a fool of myself! ;)”

“I have dyslexia so sometimes I’m worse that spellcheck. On the upside, my messages are usually hilarious because of it 😉 Plus most creative geniuses are dyslexic…the stats are in my favor!”

1507760_10152392614860079_8379465670289960282_n copy 2By Maria Montgomery – Maria is a freelance writer, director and social entrepreneur. She’s also the spokesperson for The Little Angels Community Center and an avid blogger. You can find her somewhere between Cape Town, London and L.A., where you will most likely find her in the hills, looking out over the city she loves. @OhMyMontgomery


  1. Bianca

    March 23, 2016 at 8:10 am

    Ok so in monday i was playing xbox and noticed my crush won playing also. I thought ut would be cute if i messaged him, so i sent him a message saying i bet you cant level up in the next half hour in COD but he never responded but wgen i checked what ge was playing ge swirched his games to COD. So tge next day i was texting my friend and i thought i sent her this message of me comparing my picture with him to a picture he has on insta with this other girl but i ended up accidentally sending it to him. To make it worse i dont gave social media so there shouldn’t have been a reason i had that photo. He hasnt responded either to that message. I am so scared now that he doesnt like me and he thinks im some sort of stalker!!!!

    • web admin

      web admin

      March 28, 2016 at 8:08 am

      There is nothing that you can really do at the moment. Wait and see what happens. He may not realize you do not have social media, he may just think you have a crush on him or he may not have paid attention to it. Don’t make a move or ask him out now because there is always a chance that he finds it odd. Wait for this to die down and see what happens.

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