How to date with confidence and have fun

Dating is tricky business; like trying to recreate a cake on Instagram, it has the potential for greatness, but often falls short of the dream. We want to date with confidence but it all feels so nerve-racking.

We get the courage to step back out there and try to find someone decent and caring to spend time with, but we end up with a bunch of strangers, who get waaay too familiar too fast and disappear at the slightest mention of ‘are we still meeting up tonight?’. 

Narcissists, bludgers and ghosting – oh my!

How are we supposed to find our Mark Darcy in a sea of Daniel Cleavers? And if we do find them, how to we stop ourselves worrying they will hurt us like the last one did?

Fear not, dear independent and empowered one! Dating doesn’t have to be a stressful endeavour full of wasted outfits and regret. You have the power to turn this ‘sitch’ into an opportunity for fun, excitement and the potential for longer lasting love.

All you need are the five R’s so you can date with confidence and have fun.

How to date with confidence and have fun


Have you ever tried going to the gym with the flu? Tried to clean the house with a hangover? Tried to help your kids with their homework when you’ve had zero sleep and an early start?

It doesn’t feel the best, right?

The same goes for relationships, and the need to recover from past hurt. Going into a high-pressure situation like dating without coming from a position of strength means we don’t always make the best choices for ourselves long term, and instead choose the things that make us feel better in the moment. It also means we allow our fear of what happened to us in the past to cloud our view of potentially awesome people.

If you want something to succeed, give it (and yourself) the best chance possible. You will know you are ready to date when you are prepared for the possibility that it might not work out. If not, do your homework first and get that recovery going!


In order to find the right person, respect is key – for ourselves, and for the other person.

Respect is about knowing what you will and won’t accept going in, and sticking to it. It also means having realistic expectations of whomever we’re seeing, and what you hope to achieve by meeting them.

Imagine expecting to find someone who is kind, caring, wears a suit, has a fat wallet, can cook, clean, build, won’t look at anyone else, has a flash car and a house in Byron Bay. Now imagine someone is expecting that of you; It’s A LOT of pressure.

Don’t look for a saviour. Girl, you can manage just fine on your own!

Instead just understand that that person is just another ‘you’ looking to share part of their journey with someone. Date with confidence by paying for your own dinner, making your own way to (and from) dates and maintaining your power, but be open to new people and experiences! 


Think of those times you’d go and hang out with your friend, get dinner, maybe some wines? You get to talk about all sorts of things, experience that new restaurant you’ve been wanting to go to, but you’re not too fussed if you don’t see them for a bit. This is EXACTLY the approach we should take with dating.

Remember, you’re meeting someone new; you don’t know pretty much anything about them, and you need time to do that – so take the pressure off! If you really want to date with confidence, you could go so far as to prepare some questions to ask on your first date!

Often we get caught up in what we hope someone will be, rather than who they are; and in doing so, we either get waaaaay too attached too early and scare them off, or we are bitterly disappointed they aren’t the person of our dreams.

Dial the dreaming right down, and be present in the moment. It is just an opportunity to get to know someone more, and assuming there aren’t any complete red flags (i.e. they just made bail, and oops forgot their wallet on the way over), then relax into it.

How to date with confidence (cont.)


You are having a moment away from home where you don’t have to think about anything other than YOURSELF and WHAT YOU WANT! How cool is that! And as a complete bonus, it may include getting dressed up in something pretty, having a meal you didn’t have to cook yourself and spending some time with an adult person that just may be as awesome as you are. No kids, no housework, no grocery shopping; just you, a gorgeous, sexy, empowered woman looking to expand the portfolio of your amazing life.

As a single mum, you will know that there are rarely opportunities to actually take a breather and enjoy the hell out of something for yourself, SO OWN IT!

Relish that damn outing and swim in everything is has to offer you, partner or not! The end result of a date should always be enjoying the moment, whatever it may bring to you.


As much as I would like to think that my annual trip to the gym would garner me the body of a Victoria’s Secret model, it needs ‘slightly’ more attempts than that.

The same goes for dating.

You are an individual in a world of more than 7.6 billion people, and I’m afraid to say that there may be one or two of them that won’t be the right fit for you. I know you hear the stories of a friends’ friend who met someone on Tinder and they’re now married etc. but that is the exception, NOT the rule.

The reality is we are all unique, with different values, standards, desires and prioritising of punctuality. We need to understand that in such a big pool there is bound to be a few misses along the way. Five bad dates in a row is not a sign from the universe, or an indication of love in general. Dating is a numbers game, and requires patience and persistence.

That amazing someone is out there looking for you too; just enjoy the process and don’t give up!!!  

My final word: How to date with confidence

There you have it—your foolproof guide on how to date with confidence and have a blast!

Remember, dating is not an Olympic event, so don’t sweat the small stuff. Embrace the awkward moments, laugh at your own jokes (even if no one else does), and always be yourself.

Dating doesn’t have to be scary and disappointing. Just make sure you do the right preparation, and have the right expectations going in. This is a time for new opportunities in your life, so own it and have fun.

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