10 mistakes insecure men make in the early stages of a relationship

The early stages of dating are tough as hell, I know.

Making a fool of yourself on at least one occasion is bound to happen.

Lucky for you, the right person will laugh it off (or laugh with you).

But obviously we want to avoid slipping up and making those mistakes.

Being insecure tends to make things far more difficult as it is, so why make it even harder for yourself?

If you are dipping your toes in the stages of early dating, remember to keep these 10 common mistakes in mind and avoid them where possible:

1) Not listening

I get it, you’re overjoyed to have bagged a date. 

The words start pouring out of your mouth beyond your control. 

Before you know it, you’re telling her about the snail collection you had when you were little. And the fact that you hate Vegemite.

By the time the end of the date rolls around, think to yourself:

Have you asked her any questions?

What do you actually know about her life?

It’s easy to get wrapped up in rambling on about yourself in a desperate bid to fill any awkward silences, but it does little other than to make you look arrogant and obtuse – even if that wasn’t your intention.

Instead, make sure to engage with your date or partner, listen avidly, and ask open-ended questions to demonstrate your interest.

2) You end every text with a X

Please, let the era of the X end.

“hows you xx”

“wuu2? X”

“aww that sounds nice X”

“cool me too xxx”

Although perhaps a predominantly British trait, the necessity to tag an X on to every text message no matter the topic does eventually start to grate on some people.

Some recipients might like it. 

However, it begins to sound insincere and a bit childish, so start dropping the kisses.

3) Flirting with anything with legs

What better way to show how sexy and sought-after you are than to wink at the waitress and charm the cashier?

No really.

Flirting with people other than your date particularly in her presence does you absolutely no favors.

In fact, it just makes you appear disloyal and a bit desperate, so nip that behavior in the bud.

4) Being late

Hopefully, as a slightly insecure individual, you’re turning up early. 5 minutes early, even 10 minutes is a good approach.

But turning up late is a whole other story.

You’re not coming across as cool by rocking up 20 minutes late ‘because you had some important business meetings to attend to’.

Disrespecting someone else’s time by showing up late to pre-arranged dates just makes you seem self-centered, so avoid this at all costs.

5) Talking about all of your previous conquests

A ladies man, are you?

Or were you, should I say.

Some men have a strange preconception whereby they think that bragging about all the notches on their bed posts will make them seem attractive.

Bad news.

Rambling on about your exes or past flings isn’t a good date topic. 

It just comes across as an insecure person’s attempt to seem wanted, and this show of being wanted by other women will likely send your date running for the hills.

6) Taking forever to reply to messages

Gotta play it cool, right!


Games are for children.

True, life is busy and answering every text within seconds is often impractical (and equally comes across a little desperate).

But trying to play the mirroring game whereby you wait 3 hours for a reply and text her back in 4 hours turns into a long and monotonous game.

The end result is usually the death of all conversation and a loss of interest on both parts.

Avoid playing games in person and on text, and instead reply when you have time and when it suits you both.

7) Blowing up her phone

On the flip side of taking millenniums to text back is constantly barraging your love interest with messages.

Good morning baby!

I miss you!

Thinking of you cutie!

What are you up to?

Why haven’t you replied?

Is everything okay?

….do you still like me?

You get the picture.

Healthy communication means consistency, which is not overloading your partner with a constant stream of texts, nor trying to check up on her every move.

Stay in contact, keep it short and sweet, but respect that you both lead individual lives.


I have for you a red pill and a blue pill.

The choice is yours.

Either you jump the gun, swallow the red, and profess your love immediately

Way too soon for what is considered the healthy course of a relationship.

Or, you swallow the blue and never let those three words pass your lips.

Neither is a good option for when it comes to the early stages of dating.

Premature confessions of love and adoration will only come across as love bombing and tend to scare off love interests.

Equally, never getting round to confessing your feelings will leave your date feeling confused and undesirable.

Every relationship is different so it’s up to you to decide when the time is right to take things to the next level and express your emotions.

Just be cautious of doing it too soon or not at all.

9) Keeping their date locked away

Up in a tall castle with the key tossed away, a bit like a modern day Rapunzel.

But seriously, much in the same way that you need to find a good time to profess your love, you also need to really consider how and when to introduce your date to your friends and family.

Too soon and it’ll seem like you’re rushing into things without thinking.

Too late, and it’ll seem like you don’t want to introduce them. Cue a whole host of issues such as doubt and worry on their end; that they’re not good enough for you or that your parents won’t like them.

Post the 3 month mark is a good time to start considering integrating your date with your friends and family.

When doing so, try to find a relaxed atmosphere to put everyone at ease and make it as comfortable as possible.

10) Negging

My own personal hell.

One very odd tactic used by typically insecure men is to neg partners, dates, or potential love interests.

For some bizarre reason, some men (and women) think that insulting or undermining their dates will win them over.

Newsflash: it doesn’t.

In fact, negging not only undermines the confidence of the recipient, but also makes the person doing the negging look dumb as hell.

In a world where so much misfortune and maliciousness exist already, why decide to flirt through actively nasty remarks?

Scrap the negging and replace it with kind and genuine compliments. It’ll get you a lot farther in the long run.

Final words

Everyone makes mistakes in relationships, particularly in the early stages.

However, if you’re aware that you’re not the most confident individual out there, use this list wisely.

You have so much to offer (even if you do sometimes find yourself doubting that), and it is through putting yourself out there and giving it a go that you’ll meet your perfect partner.

But when that happens, you don’t want to spoil it by using any of the above tactics.

Instead, treat her (or him) with kindness and compassion.

Lead your own life but come together when it suits you both, and express your feelings when the time is right.

You’ll be well on your way to a happy relationship in no time.

If you display these 12 behaviors, you’re starting to value yourself

If you want true inner peace, start saying ‘no’ to these things