5 ways to level up your dating life

Audrey Claire, My Wingwoman Founder & Coach
Nov 25, 2019

Want to connect with more people, form closer bonds, date on your terms and feel more satisfied in life in general?

Yes! That’s exactly what I thought you’d say.

Well go on then, read on 😉

In an earlier blog I discussed my belief that COMMUNICATION is THE most valuable practical area we can improve to transform our dating life.

Here’s 5 focus areas to level-up your communication skills and how they can give your dating life a boost.

1. Practise assertive communication

Sometimes assertive communication gets a bad rep simply because it often gets mislabelled as aggressive communication and vice-versa. So, it’s important to understand exactly what it is.

I really like this definition from psychologist and best-selling author Edmund Bourne. Bourne describes assertive communication as:

“asking for what you want (or saying no) in a simple, direct fashion that does not negate, attack, or manipulate anyone else.”(1).

Bourne also points out that it involves “taking responsibility for getting your own needs met in a way that preserves the dignity of other people.” (1)

(As an aside, I love that word: dignity).

That last part is really important. Considering and respecting your audience is not only what makes assertive communication distinct from aggressive communication, it’s also what makes it more effective in the majority of situations.

Assertive communication is a big topic in its own right (and we’ve got 4 more focus areas to get through), so let me just say this.

By making assertive communication a mainstay of your dating toolkit, not only are you more likely to get what you want, you’ll find it easier to sort the sheep from the goats, feel empowered, be viewed as confident and experience far less frustration.

To make this a little more real, I want to give you an a little ‘before and after’ example of assertive communication in action.

In this hypothetical text exchange, imagine “Tina” is keen to catch up with “Jason”, with whom she’s only just started dating. Imagine it’s a Wednesday and Tina wants to see Jason this coming weekend.

What not good looks like…

Tina: Hey what’s on for the weekend?

Jason: Hey! How’s it going? No big plans yet, thinking about heading to a mate’s BBQ on Sunday. You?

Tina: Oh nice, I love a good BBQ. Sounds like fun. I’m not sure yet, thinking about just having a quiet one this weekend.

Jason: Yeah it’s nice to lay low once in a while.

Tina: Yeah, I mean it’s been a busy week at work already. How was your week treating you?

Jason: Yeah pretty busy, usual stuff. Nothing much to report but looking forward to the weekend that’s for sure.

Tina: So would you like to catch up sometime?

Jason: Yeah sounds good, you mean this weekend?

Tina: Yeah this weekend if you’re free?

Jason: Sounds good. Let’s touch base later in the week.

Tina: Cool, enjoy your Wednesday

So why is this a #fail?

Jason could be forgiven for thinking Tina was just making casual conversation. Yep, it’s true he didn’t exactly take the bull by the horns here by suggesting firm plans, and that’s on him, but the side of the convo Tina can control is definitely lacking assertiveness.

Tina was worried about rejection and hesitated to directly ask for what she wanted, BUT by being so passive and skirting around the topic, she’s going to experience an even worse feeling: being in limbo for days!

If you can relate to Tina’s side of this convo I want you to practise this little 3-step process to be more assertive.

  1. Check in with yourself and ask: what is it I really want out of this interaction?
  2. Ask yourself: is my request valid and reasonable?
  3. Own it.

Okay so here’s what good looks like…

Tina: Hey what’s on for the weekend?

Jason: Hey! How’s it going? No big plans yet, thinking about heading to a mate’s BBQ on Sunday. You?

Tina: Oh nice, I love a good BBQ. Weather is meant to be awesome all weekend. Want to grab a drink with me Saturday arvo at that beer garden near yours?

Jason: Sounds like a plan. I’ve got some stuff to do around lunchtime but free after that.

Tina: Okay cool, how about we meet at 2?

Jason: Yep that works.

Tina:  Cool. I might get there a little earlier to snag us a good spot. Don’t be late or I can’t guarantee the beer I’ll have waiting for you will still be there.

Jason: Haha okay, 2 on the dot it is then 😉 Speak later in the week.

See how much easier that was! Even if Jason hadn’t been as receptive to Tina’s suggestion, at least she wouldn’t be in limbo because of the assertiveness in her request.

On top of that, she’s even found a cheeky way to make Jason aware she’s not a fan of being kept waiting and in the process sounds WAY more confident in who she is.

Tina you QUEEEEN!

2. Pay attention to body language

Want to be more approachable, attractive and charming? A LOT of the answers lie in body language.

I love this quote from American producer and author Peter Guber that really sums up how I feel about the power of body language.

“Language is a more recent technology. Your body language, your eyes, your energy will come through in your audience before you even start speaking.” –


One way you can become a master of body language (BL) is to first become a close observer of it.

It’s impossible NOT to learn a thing or two simply by watching other people interact.

Now, I’m not suggesting you lurk around the office secretly observing your colleagues!

All I’m saying is, as you’re out and about doing your thang, start noticing the subtleties in body language that makes someone more approachable, more charming or appear more confident.

Here’s one teeny tiny example of how body language can give your dating life a boost that’s helpful no matter if you’re a man or a woman.

One thing I’ve learned by being a close observer of BL myself is that the people who often get noticed and viewed as more confident and attractive are the ones that walk around with their eyes up facing outward, instead of looking at the ground.

Try this out on your next date…

As you approach your date for the first time, keep your head up and look at them as you make your way over to them. Don’t be coy and look at the ground. Instead, smile, make eye contact and let them know with your facial expression that you’re confident, warm and open to connecting.

Bonus tip: don’t wait till the second date to do this, your opportunity to make a strong first impression is over.

3. Be choosy about context

No communication is free of context.

Two important context considerations for dates are:

  1. Physical environment and
  2. Time of day

You can have better dates just by being considered about WHERE and WHEN you have them.

Do your research and pick a venue that suits the mood you want to create.

Looking to ramp up the romance a notch? Pick a well-lit bar or restaurant where you can sit next to eat other.

Looking to inject a bit of playfulness and spontaneity? Suggest an activity like a walk followed by a drink or mini-golf instead of just a typical seated date.

Looking for a platonic friendship only? Pick a coffee shop!

Picking the wrong time of day or day of the week for your date is one of the easiest ways to shoot yourself in the proverbial foot.

Want to make it clear you’re not interested in sparking ANY chemistry? Pick an early AM timing for your date. Even better, tell them you have plans straight after. That’ll really get the blood pumping.

Want to feel distracted and generally make it harder to form a meaningful connection? Pick a time when you’re super tired and then squeeze your date into exactly THAT window. Right after a really demanding workday is usually best.

You get my point.

4. Get feedback

By this I don’t mean you lean across to your date and ask:

‘So…. how am I going? Am I in with a chance or what?’ Although, come to think of it, that might be kind of charming delivered in JUST the right way, with Hugh Grant-esque humility and charm. But I digress…

What I really mean by ‘get feedback’ is two-fold:

1.Seeking constructive feedback from people you trust.

To get better at anything, we need an awareness of both our strengths and weaknesses.  Even if you’re incredibly self-aware, seeking the feedback of others still has value. You just never know what little insight could take your skills to another level.

A word of warning: only seek feedback from those who will be fair and constructive. Also, when asking for the feedback, give the person you’re asking permission to be honest (and be prepared for the response).

2. Feedback IN the interaction

This means paying attention to the feedback that’s quite literally written all over your date’s face. Sometimes you might need to pay REALLY close attention, but it will be there in their facial expressions, posture, mannerisms and vocal qualities.

For example, imagine you’re on a first date and you hit on a topic that lights your date up. They seem to love talking about their passion for adventure sports.

Their face lights up, their mannerisms become more animated and they’re talking faster. Even if your idea of an adventure sport involves trusting a ‘Netflix recommends’ movie choice, it might be a good idea to stick on this topic for a while because a) you never know what you might learn b) you’ll be more likely to see your date at their best and c) you’re saying ‘I’m interested to know what makes you tick without really saying it.

And what’s not to like about that?

5. Seek to find common ground

Deep down, we all just want to feel good about ourselves, feel we matter, feel understood and connect with others.

If you care to search for it, you can find common ground with anyone.

Even the WORD “communicate” has Latin roots that mean ‘to make common’, ‘to share’ (2).

Better communication is better relating.

All of these examples below stem back to better relating:

  • Acknowledging how someone is feeling ‘You must be tired after the week it sounds like you’ve had!’
  • Finding things in common ‘No way, you’re from a country town as well?! Don’t tell me you lived on a farm as well?’
  • Seeking to understand someone’s perspective ‘I’m curious, what made you get into Yoga?’
  • Matching and mirroring someone’s body language If they have a relaxed pose, match it without obviously copying every single thing they do. This says ‘I’m present in this interaction with you’ without actually saying it.
  • Focusing on positive, easily relatable topics of conversation I like to call ‘levellers’ Food, animals, travel, film, TV and yes sometimes if you’re desperate even the weather can be levellers.

While this is by no means an exhaustive list of what you can do to level up, focus in any one of these areas could bear fruit no matter what your starting point looks like.


  1. Bourne, Edmund J. The Anxiety & Phobia Workbook. 6th Edition, New Harbinger Publications, 2015
  2. Hargie, Owen. Skilled Interpersonal Communication : Research, Theory and Practice, 6th Edition, Routledge, 2016.

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