I was walking by the stairs of the Melbourne GPO during the peak hour rush one evening, strutting my stuff in a pair of 4-inch patent black heels and a black pencil skirt; When an unfamiliar voice called out to me from a distance. I turned and there he was, tall, shaved head, blue eyes, chiselled; perched on the steps of the GPO; perfection, hot, movie star hot with a resemblance to the prison break star, Wentworth Miller. ‘Excuse me, Miss, is there a great place around here where I could go for a drink?’ he called out. ‘Sorry, I don’t socialise around here,’ I automatically replied. As the words flowed out of my mouth, an internal war began raging in my mind; ‘What are you saying, this guy clearly thinks that you’re a goddess and you’re messing things up.’ As I break free from the battlefield of my mind, I notice my Wentworth Miller look alike shaking his head and laughing to himself. I dash off into the peak hour crowd buzzing around me and I never see him again. ‘He could have been the love of my life and I messed it up, argh!’ I scream internally. Another awkward dating moment to add to the list.

I just love an awkward dating moment they make incredibly funny stories after the flushed complexions fade away. I could have spent that evening snogging a hottie; he clearly thought I was a goddess and I messed that up. Unfortunately, this isn’t the first time that I have self-sabotaged my way out of a perfectly great opportunity. What can be learned from this experience and how can I change my behaviour to prevent reactions like these from reoccurring in the future? How do you stop this tendency to self-sabotage?

1. Talk to more people.

As I look back and assess my awkward dating moment it has become clearly self-evident that I need to talk to more men. When you start a personal training session or a vocal lesson you first warm up the muscles involved in the session and in a similar way I need to be constantly warmed up to feel confident when communicating with the men I feel attracted too. Previously, my approach to life has been direct and I have taken this approach to my love life, if I like a guy I find a way or an excuse to talk to him but I tend to ignore all of the other people who exist in my day-to-day life; my approach has not left me fruitless and I have gotten it right on other occasions, however, this particular moment does not reoccur. By engaging with the people around me on a daily basis I am more likely to feel comfortable, flirt and focus on creating a connection than bumbling my way through an awkward conversation with a potential love interest.

 2. Practice makes perfect.

It isn’t enough for me to engage with the people who I encounter, on a daily basis; I need to be more playful and less serious with my interactions. My awkward dating moment with my Wentworth Miller look alike would have been far less awkward if I had simply adopted a playful outlook but not just at this moment but all moments. I am certainly not saying to be excessively flirtatious with every man who I meet but simply playful. After all, it’s a playful outlook is what makes you more attractive not just to men but with everyone. Matthew Hussey’s book, Get the Guy, perfectly illustrates how to adopt a playful outlook. ‘To be playful is to take ourselves, and our interactions, less seriously. Adding a hint of playfulness in conversations with guys is how we create chemistry. Joking around, teasing, telling funny stories and being silly are aspects of playfulness that make us more attractive and charismatic.’ The more I inject a playful undertone in my everyday conversations, the more at ease, natural, and less awkward my interactions will be with the men, who I feel attracted to.

 3. Be present.

One of my biggest challenges is to simply be present. I’m always thinking of my next blog post, career move, rushing to and from venues with my iPod blasting in my ears and my purse in the other; my life often has little room for spontaneity. By making a few small tweaks to my daily rituals can create endless possibilities. If I restrict my iPod usage to the gym only, switch off and enjoy my lunch breaks by keeping planning to the office; I will be more aware of the opportunities that surround me and be more prepared as well as open to spontaneous conversations like the one I had on the steps on the Melbourne GPO.

Talking to more people, adopting a playful outlook and being present in the everyday moments is the best way for me to avoid an awkward dating moment and to prevent any future self-sabotaging behaviours. Have you found yourself in a similar situation? Please let me know using the comments box below.


With love,

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Amelia Hay

Author + Coach at Amelia Hay International
I help multi-passionate women just like you to package, brand and market your passions so that you can create your dream business and life, find clarity, confidence, and clients, and make a difference in your world.
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