How to start a text conversation with a guy? [5 KEY TIPS]

Welcome back to Text Sensei, the place where we teach you to text better. After all, texting is playing an increasing role in our everyday conversations, right? Today, we are talking about how to start a conversation with someone you like or are interested in by the power of text messages. We want to do text chat in a fun way without coming across as awkward or boring. This is what we want to show you today!

What is our aim here?

Put simply, what are we trying to do here? Well, we want to engage someone we have a ‘crush’ on with an interesting and fun conversation that will make a lasting impression on them. We want to pique their interest and make it so they want to reply to you.

Boring or cliched one liners won’t work here. This is not your life partner yet, so more effort and thought is needed!!

Just be aware that these tips are designed for use on people that you have already met or know in some way. Approaching a complete stranger is totally different!

What’s the key?

Whilst making our text conversation interesting, we also don’t want to make it too short and in a way that puts the pressure on the other person to come up with or produce an end result 🙂

As well as having the potential to be boring and aimless, a bad text conversation could also put pressure on the other person enough to make them not want to respond.

So texts like ‘What’s up?” “How are you doing?” and other typical one liners won’t work here, sorry! They are too simple and don’t show any care and attention, something you need to achieve in order to grab the other person’s attention.

When you send such texts, you are going into a conversation without a plan or a direction, which often ends in disaster. Especially when it comes to people you like or have a crush on.

So how should I approach this?

Here are our essential tips for talking to guys over text!

Tip 1. Choose the right topic!

It is likely that this person you like and want to get closer to is someone you work or go to school with. Your lives are likely to be connected by something mundane and boring. Often, these everyday connections don’t make great starting points for interesting conversations! The latest office gossip or gripes aren’t going to engage most people that are still quite new to you . These are the topics you save for when you are life partners or married 🙂.

Before you start such a text conversation with a potential partner or ‘crush’, try to plan a head a little. You want this conversation to be interesting and engaging for both of you.

Instead of topics around the daily grind, think of a subject matter outside of this that interests both of you and set up the conversation from there. To give an example, maybe you know that this ‘crush’ has an interest in pop music. You could start by telling them you heard a new song on the radio but are not sure if you like it and ask for advice.

If the other person is truly interested in the subject matter, they will willingly respond and carry on the conversation passionately. Job done!

Think of it as a shared passion or interest that is simple but allows you to share opinions on.

Tip 2. It’s all in the opener!

It’s always best to approach these text conversations with a fun and light-hearted approach. This will help put the other person in a positive frame of mind at the very start.

The best way to do this is to make your first line have a joking tone to it. Humour will lighten up any situation, trust me!

So, with the pop music example given above, I would start the text conversation with something like…..

“That X song just come on the radio, can’t work out if it’s genius or garbage :)”

Funny openers like this will prove far more likely to turn into successful text conversations.

Tip 3. How to move on…..?

It’s fair enough to start with a fun and engaging topic to start a conversation with the opposite sex, but where do you take it from there?

Slowly and subtly start to transition from this ‘fun’ topic into things that are more personal.

With the music example, you could start talking about music you like and ask what music they like or listen to often? How your favourite music makes you feel, or memories it reminds you of (don’t talk about your ex though!! Ha ha).

This is how to lead into a more personal topic from the initial light hearted opener. Take some moments to think about this but don’t overthink it or spend too long analysing how to lead into this new topic. You want it to come across as natural, not rehearsed!

And texting is a great way to work as it gives you plenty of thinking time in between each text 🙂.

Tip 4. Building a personal connection

What you are doing here is building a personal connection with the other person, talking about things that lead to many forms of engagement between you. These are the very sparks that can interest the other party and take a relationship further.

It allows you to have a deep discussion, share a joke, or even discover topics to tease each other about. All these things deepen the connection.

With this in mind, don’t be scared to be opinionated. Some people think that at this early point in a relationship that you should not show strong opinions and be more like a ‘yes man’. This is actually the opposite of what you should do. Your opinions show who you are and people will often be drawn to this. A blank page is not exciting or attractive to anyone.

Tip 5. Don’t get too heavy too fast!

Don’t forget that often you are texting someone that is new to you and you have a desire to take a deeper interest in them. Don’t scare them off by using boyfriend-girlfriend talk too early. Don’t say someone is cute or sexy, or start talking about love. This will more than likely lead to a quick stalemate, not a soulmate!!

What are you waiting for?

There you have it, our full rundown on how to text someone you like and want to try to deepen the relationship. And, if it scares you, think about this. Years ago, you would have to do these conversations in person or over the phone. A text conversation is way easier than this, and it gives you way more thinking time to get these important conversations right.

We would love to hear all about your texting successes and failures in the comments section below 🙂 I’m sure we all have them 🙂

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