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Mistakes people make when they first start texting someone they like

Some of the common mistakes people make when they first start texting someone they like, and how to avoid them.

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When you first start texting with someone you like, it's hard to retain your cool.

It's easy to feel needy and unsure of yourself.

While it's perfectly natural to feel this way, you don't want to make it obvious to the person you just started texting with.

If you're at risk of exposing your needy, unsure self, you need to avoid the following common mistakes people make when they first start texting someone they like:

The '?' or 'Hello?' message

Texting someone you like makes you feel vulnerable.

Minutes feel like hours as you wait for their reply. 

While waiting, you start to think 'Why haven't they texted me back yet, they've seen my message' or 'Surely they'd be on their lunch break by now, why haven't I had a response?'

After some time, the nervousness of the situation overwhelms you, and turns into impatience.

The problem is, revealing this impatience to the other person (especially in the early stages of your texting relationship with them) makes you seem desperate, disrespectful and insecure.

Look, they've likely seen your message. They've probably even had an opportunity to respond. But, they also don't owe you anything. Not yet, at least. After all, you're just starting to get to know each other. 

Instant responses from someone you just started texting aren't a given.

They're earned.

Be patient, play it cool and instead of backing up your unresponded message with '??' or 'you still there?', put your phone down and distract yourself with literally any other activity.

The 'I thought you were going to sleep?' message

If they tell you they're about to go to sleep, wish you goodnight, but you see them online on Social Media an hour later, DO NOT question them about it.

You may think you're being cute and funny when you drop a quick 'I thought you were going to sleep?' text to them, but you're not. 

You're telling them that you have major trust issues.

Some people like to say goodnight to others early, so they can have an hour of uninterrupted, mindless Internet browsing time before they go to sleep.

Some people say goodnight to someone because they genuinely believe they're about to go to sleep. Then they have trouble sleeping, and so they get on their phone and check their Social Media accounts. 

Don't jump to the conclusion they're lying to you and trying to avoid you, and certainly don't accuse them of doing so. 

They'll only resent you for it.

Overdoing the GIFs

Amusing GIFS can be a great addition to a fun text conversation with someone you like.

Throwing them in any chance you get waters down their impact. 

Save them for moments where the opportunity to use them surfaces organically.

Really poor grammar

If you're an adult, text like one. Especially if you're having an in-depth text-based conversation with someone you like. 

You don't need to be the world's greatest poet when you're texting, but full-stops, proper grammar and correct use of 'their' 'they're' and 'there' shouldn't go astray.

Next time you're about to press send, don't forget to read over your message and briefly check for any errors.

Opening every conversation with 'Hey, how's it going?'

There's nothing wrong with a 'Hey, how's it going?' from time to time. It's familiar, it's casual, it's easy.

But when it's the only phrase you use to start a conversation every time you speak with someone you like, it can begin to have a negative impact on your initial relationship with them.

Here's why:
- It doesn't give them much of a platform to continue the conversation beyond 'Good, you?'
- It seems lazy, boring and ill-conceived on your end to perpetually use the same mundane opening message.
- There's only so many times in a week someone cares to tell you how they're going. Eventually, the question will lead to a response like: 'Same as last time. Good.'

Waiting for the right moment to ask them on a date

If you believe that you need to wait for the perfect, romantic, organic moment in which to ask someone on a date via text, that moment will likely never come.

There's nothing wrong with being direct and dropping it into a conversation at random.

There's plenty wrong with sitting on the periphery, dancing around the subject, and never making a move.

Disclaimer: I'm not saying go in for the kill straight away, but weeks or months of endless, slightly flirtatious texting, with no view of progressing that flirting to a real-life date, may make them start to lose interest.

Sending them a 300-word proposal instead of simply asking them on a date

When you want to ask someone on a date, it's important to do so confidently and casually.

Long, drawn-out messages seem weak and put too much pressure on the situation.


'Hey, so, I was wondering, if you're free next Friday, (I know you're popular so you probably have plans, hehe) would you maybe want to go for a drink with me? Or maybe dinner or something instead if you don't feel like drinking?'

Drawn out messages like these suggest you don't feel you're worthy of a date with this person.

If you don't seem like you feel you're worthy of asking them on a date, chances are, neither will they.

'Hey, want to come to that new bar that opened in the city with me next Friday?' is a completely acceptable way to ask someone on a date.

Using a humble-brag to prove your value to them

Humble-bragging involves hiding a brag behind humility.

Examples of humble-brag type text messages include:

'I just got promoted to a Director position at work. I'm freaking out cos I'm the youngest person in my company's history to do so! Send help!'

'Between partying with all of my friends, going to the gym and destroying myself at work, I rarely find time for myself. It's hard being an over-achiever.'

When you first start speaking to someone you like, you want to show them how great you are, while portraying modesty about your accomplishments.

By resorting to a humble-brag in order to do so, you're telling them the opposite.

If you want some more information on the dangers of humble-bragging, check out our article on it.

Hammering them with questions when the conversation runs dry

If a conversation with the person you like is running dry, don't try and rehydrate it with a barrage of questions.

Take the hint if they're genuinely not interested in texting with you right now.

Ending a conversation because it's gone dry is no reason to feel you're down and out altogether. It's just a sign that perhaps they're too busy or distracted right now.

The 'hiding insecurity behind genuine concern' message

This is the 'Hey, you never responded to my message, I'm worried about you. Are you ok?' message.

If you don't know this person very well, your overbearing concern for their wellbeing based on a few hours of unresponsiveness via text-message is off-putting.

It's quite similar to the '??' message, but instead of making you seem pushy and impatient, it makes you seem insecure and as if you're patronising the other person.

They're fine. 

They were fine long before you started checking in on them. 

Be cool. 

You shouldn't be doting on them and concerned for them long before your relationship with them has matured to a point where it calls for it.

Subtly confirming a date with them many times before the date

When you do manage to lock in a date, your cynicism starts kicking in. 

You feel like it's too good to be true and that they'll almost certainly cancel on you.

To alleviate this worry, you subtly confirm the date any chance you get. 

You text them something like 'You'll have to tell me more about that next Friday', or perhaps a 'So, this place we're going to next Friday does great Cocktails, do you like Cocktails?'

The problem with these subtle confirmations is that they scream insecurity and can make the other person second-guess their decision to go out with you.

What you should do instead:

Confirm the date, but do so directly, and no more than twice.

If it's been more than a few days since you first set up the date, and it hasn't been mentioned since, send them an: 'Are we still on for Tomorrow?' message the night before, and a time/location confirmation message on the day of the date.

Final thoughts

It's hard to be cool, calm and collected when you first start texting someone you like.
It takes trial and error to master the craft.
Almost everyone is guilty of making at least some of the mistakes I listed above, but have still gone on to progress their text-based relationships with others into successful, real-life relationships.
Just do your best to prevent them as best you can in future, and your dating life will be all the easier for it.
Good luck!

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