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How to Start a Conversation with a Guy Over Text

by Sonya Schwartz

Do you have no idea how to start a text conversation with a guy? 

Are you letting some seriously sexy Tinder matches slip through your fingers because of your boring chat? 

Or maybe your first dates aren’t transitioning into second dates because he loses interest in texting with you?

If so, you’re in the right place. This guide features nine expert tips to spice up your text messages.

However, before you take note of these tips, read the next few sentences carefully. 

The tactics listed in this guide will help to maintain his interest, but there is one thing you absolutely need to do to keep a man around in the long term. 

You have to appeal to his emotions. 

As long as you can do this, it’s unlikely to matter what text messages you send.

That’s why I want to share what happened when I discovered a little-known aspect of male psychology called the ‘Hero’s Instinct. 

This psychological trigger has a huge impact on how he feels about the women in his life. It’s a mindset that all men seem to embrace.  

Once you know how to poke at it, he’ll often become far more emotionally attached to you. (click to read how I discovered this).

This could be the difference between becoming ‘the next pretty girl’ or the woman he obsesses over. 

What’s more, it’s an easy skill to master once you know how. 

If you’re hoping to make a lasting impression on a special guy, it’s well worth learning how I discovered the ‘Hero’s Instinct’.

With that said, here are nine additional ways to spice up your text messages.  

Make it Interesting

One of the worst things you can do when you’re starting a conversation over text is to make it boring, generic and closed, as this will make you unlikely to get a response.

There’s plenty of time to discuss how they are or whether or not they’ve had a good day, so before you send them a text saying ‘how are you?’, think about how you could make it a little more engaging to ensure you get a reply from him and strike up an interesting conversation.

Instead of generic questions, think of something they’ve told you recently. Were they studying for a big exam when they last saw you? Or were they just in the process of moving house? Making your opening text personal and engaging will increase your chances of getting a reply and also make him realise what a good listener you are, gaining you extra brownie points!

However, you’ve got to be extra careful with this one if you’ve been secretly peeking at his social media channels, as you want to avoid blowing your cover by asking him about his recent holiday or how his dog is if these are things you’ve seen on his Instagram. Otherwise he might get the impression that you’re a little bit crazy. After all, nobody wants a stalker, especially after a first date!

Example:

Avoid sending him to sleep with generic chat and increase your chances of getting a text back with the following examples:

Do

‘Hey, how did the big house move go? Are you all settled in?’

‘How was your holiday? I can’t wait to hear all about it!’

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Don’t

Hey, how are you?’

‘How’s your day been?’

Send a Relevant Meme

If you’ve got his sense of humour down to a tee, then finding a meme that’ll make him chuckle shouldn’t be difficult, and it’s sure to earn you some brownie points too - every guy loves a girl who can make him laugh!

One of the best things about sending a meme to the guy you like is that it doesn’t seem too desperate. It’s a breezy way of starting up a conversation that says ‘saw this and thought of you’, as opposed to ‘been thinking about you constantly’, making him think you’re cool, laid-back and funny - things every guy looks for in a girl!

Additionally, if the meme is relevant to something you discussed on your date, it’ll make him reminisce about how much fun the two of you had and think about how much fun you can be too, making him more likely to initiate that second date. It’s a win-win situation.

Use His Name

Using someone’s name in conversation is a great way to engage with them and grab their attention, making it the perfect way to strike up a conversation over text. However, you need to be careful not to overdo it, or it can come across as manipulative or just plain weird!

Using a person’s name acknowledges their identity and makes the text feel more personal, which is why it’s great to drop his name into a text when you’re trying to start a conversation.

From a very young age, we’re all conditioned to listen when someone uses our name. From your parents and siblings to teachers and peers, your name is your identity tag which is used by people when they want to gain your attention.

 Therefore, by using his name in your opening text, he’ll subconsciously register this as you trying to get his attention, making you much more likely to receive a swift text back. It’s a tried and tested method that works pretty much every time.

Example:

If you’re trying to make that text a little more personal (and make sure he texts you back!), then using his name is the perfect way to do so. For example:

Do

‘Hey (his name), did you watch the latest episode of (that TV series he loves) last night? I thought it was a little bit slow…’

(His name)! I went to (that restaurant he told you about) last night, the food was insane! Any more recommendations 😉 ?’

Don’t

‘What did you think of the game yesterday?’

‘How was your weekend?’

Always Ask a Question

If you’re wanting the guy you like to reply to you, then one of the worst things you can do is to send him a closed message that he’ll struggle to reply to. Instead, you should make things easy for him by always including a question in your first message - and each message thereafter.

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As we mentioned earlier, you want to make sure your message is engaging, so avoid asking him generic questions about his day or what he had for lunch. Instead, think of something interesting to ask him to get the conversation flowing and make sure those texts will be pinging back and forth.

Example:

Always try and include a question in your opening message to increase your chances of getting a reply, such as:

Do

Have you seen (Netflix series)? It’s so good, you’d love it!’

‘How was your family party this weekend? Not too boring I hope!’

Don’t

‘I got my hair cut today!’

‘I watched (Netfilx series), it’s really good!’

What to Avoid When Texting a Guy

In the digital age, it’s difficult to avoid texting the guy you like in between dates, however, there are so many things which can go wrong via text due to misinterpretations, over-friendliness or poor judgement.

Whether you’ve been dating a few months, or haven’t even been on your first date, there are a few things you need to avoid when initiating a conversation with the guy you like to avoid coming on too strong and scaring him off.

Avoid Double Texting

If he reads your message and doesn’t reply, it can be tempting to send him another text to prompt a response, however, this isn’t a good move - although we’ve all been there before!

 There might be a good reason for his lack of communication, such as a family emergency or busy work schedule, so you should give him some space and see if he replies to you in his own time. If this is the case, he’ll appreciate the space and you’ll come across as cool and breezy, so it’ll work in your favour.

However, if you’ve still not heard from him after a few days, it might be that he’s just not feeling it - his ex-girlfriend may have come back on the scene, or he may have been on another date which went really well, meaning he’s unlikely to text you back.

As hard as it might be - especially if you like the guy - you’ve got to remember that if he really wanted to speak to you, then he would. So instead of sending him multiple texts to find out why he’s not talking to you, swallow your pride and get back to swiping on your favourite dating app, otherwise he might start telling all of his friends that you’re a little bit crazy.

Don’t Come on Too Strong

If you’re wanting to initiate a second date with this guy, it’s important to strike up a conversation to establish the mood before you go asking him for date number two.

Using the tips above, start a conversation with this guy and let the conversation flow from there and avoid asking him out for another date as soon as you’ve initiated the conversation.

If he’s being open, flirty and genuinely seems engaged in your text conversation, then this should give you the green light you’re looking for that he’s interested in you. However, if he’s slow to respond and it’s difficult to keep the conversation going with him, then it might be worth moving on to someone who’s worth your time and energy!

Either way, it’s important not to be overconfident and coming on too strong, as this could squash any chances you had of a second date.

Be Careful When Making Jokes

Although it’s important to get your sense of humour across and try and make the guy you like laugh, it’s also vital that you establish what your jokes will look like over text, as they can be easily misinterpreted.

What you might see as a sarcastic, witty response, he might view as a nasty, bitchy comment, so always triple-check your texts to make sure they can’t be taken in the wrong way and ruin any chance you had with this guy.

Avoid Asking too Many Questions

Whether you’ve been dating for months or days, asking too many questions over text can be overwhelming and make him feel like he’s being interviewed. In turn, this can lead him to pull away from you or become disengaged in the conversation.

Instead of grilling him about every aspect of his life, just let the conversation flow naturally, just as it would if you were speaking in person. Limit the questions to two per text, giving him time to answer each one and making it feel less like an interview and more like a conversation between two people.

Additionally, it’s important to avoid asking him anything too personal, such as his past relationship history or sexual history, as this could make him feel awkward, as these are the kind of things he’ll share with you if and when he wants to. This is especially important if you’re in the very early stages of dating, as you might come across as too intense and lead him to run for the hills.

Don’t Wait Too Long to Text Back

We’ve all been there, waiting for a response to a text we sent hours ago. But in this day and age, it’s very rare for people to go a few hours without looking at their phone, making it very clear who’s playing a game when it comes to texting back.

Although you might not want to text him back instantly - especially if he’s taken a few hours to reply - you also don’t want him to think you’re playing games by ignoring his texts for hours on end. This is especially important if you’ve got your ‘last seen’ switched on on WhatsApp or Facebook messenger, as this is a clear indication that you’re ignoring someone!

Instead of playing games with him, seeing who can wait the longest to text back, just text him back the next time you look at your phone and you’ll come across as cool, calm and collected. After all, no guy wants to seriously date a game player, so you’ll risk losing him for good. 

By following the tips above, you’re sure to strike up a truly engaging, witty conversation with the guy you like, making him realise what a good catch you are.

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Sonya Schwartz
A hopeless romantic that struggled for many years to find her Mr "Right" and made all the mistakes you could think of while dating. Known for always choosing the wrong guys or messing up relationships, Sonya was finally able to change her approach and mindset when it came to dating which helped her eventually find the man of her dreams and become happily married. You can read more about me here...

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