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Is it OK to Ask a Guy Out First?


Tired of waiting for Mr Right to show up? Still waiting for your knight in shining armour to swoop in and “find you”?

This is such a prevalent problem for women of all ages. I have clients well into their 50’s still waiting and hoping for the right guy to show up yet failing to take action. The flip-side of this issue – that women should be more proactive in seeking and chasing men – brings up one of two reactions: “What if he rejects me?” and “Is it OK to ask a guy out first?”

The fact is that we are trained from infancy to wait – if you think of nearly every fairy tale we loved as a toddler and child, most of them involve the man taking the action - coming to find you. This is not helped by a lifetime of then being told “It’ll happen” and “Good things come to those who wait”.

Women have become ever more empowered and confident in their careers and interests yet they still hold the expectation that men will retain the confidence of olden days in chasing them. The two do not merge well. As women have become more powerful, men have become less socially sure of themselves, less secure in knowing their role and how they fit in a woman’s world.

So the old paradigm of men doing the chasing does not work in every case anymore. The problem with this is that women are mortally afraid of asking men out, and unsure as to the protocol and etiquette around this changing framework of dating.

The good news is that women can take action without really putting themselves into the rejection seat. The key lies in what I call “engineering” – creating opportunities for men to talk to you and ask you out and find it easy and non-threatening to do so. You set up the stage, they do the work and think it was their idea all along – it’s a win-win for everyone.

The first task for you is to recognise that waiting is only a small part of your options and determine to be more proactive. There is work to do before you can reap your rewards. Just keep in mind this is meant to be fun, remember? Don’t get all intense and scary about it!

Wait or Create: Should I ask a guy out on a date?

Yes. In fact, guys overwhelmingly vote that they like it and are highly flattered when a woman is proactive and asks them out – it’s a refreshing change from them being in the hot seat all the time.

But you don’t have to hit them between the eyes with “Do you want to go out sometime?”. If you want to try asking a guy out, go with “Here’s my number, give me a call next week” and walk away. It’s confident, there is no chance of on-the-spot rejection, and you give the guy some work to do – he now has to take action and do the chasing. Engineered.

Some Sneaky Ways to Meet Men

If you’re not at that level of confidence yet, the next best thing is to create opportunities for guys to chat to you. There are two sets of circumstances that you need to work around.

First, in a social setting like a pub or bar: often men will see a woman they like but will not approach her because they are not getting the right signals to reassure them they will not be rejected if they do. In this type of environment your greatest tools are eye contact, your smile, and proximity.

Hold your eye contact just a little longer than normal, make sure you have a small smile so you look approachable (the sultry pout just makes you look grumpy ladies, don’t go there!), then manoeuvre yourself (or your group) to get closer to where the guy is so he doesn’t have to walk across a massive space in view of all his mates to get to you. Unless he’s VERY confident he will not do that, even if he thinks you are the sweetest thing he’s ever seen. So if he goes to the bar, GO to the bar! Flirty eye contact, small smile, get close. Engineered.

Secondly, in everyday situations when you are out and about: you need to be watching and observing and using the opportunities that are available.

For example, I was reverse parking one day into an ample car space. There was a truck parked behind the space I was reversing into and the (rather cute) driver was standing next to his truck. I knew there was plenty of space, I was nowhere near the truck, but I used the opportunity to create an opening for him to talk to me. So when I got out I said “Have I left enough room for you?” followed by some joking about driving ability and we began a conversation. He ended up helping me unload boxes from the boot of my car and holding the door open for me while I took them into the building. I’ve no doubt I could have taken it further but I have to confess I was only practicing – I wasn’t single at the time! But….engineered.

Tips for Online Dating

With the rising prevalence and social acceptance of online dating, this is now an incredibly efficient tool for women. But it takes some smarts, the right attitude and mindset, and a very well written profile to make it work for you.

We don’t want to become every-night-online-trawlers, OR attract a million unsuitable guys. Like a financial investment where you want your money working for you in the right way while you get on with your life, you want your profile working for you so you can focus on everything besides your computer.

You need to learn to use online well to protect your positivity and confidence, and to filter through the morass to find you the right guys to date.

Some essential tips to observe:

  • Numbers are your friend, both for your chances of meeting Mr Right, and for keeping your emotions on an even keel. You need to be chatting to several men at any one time to stop yourself emotionally investing in someone you don’t really know, and to ensure that you get enough dates. Many online conversations will go nowhere and you’ll have wasted a week talking to one person. Keep at least 3 going until it becomes clear that one is genuinely interested in meeting you and is putting in the time and effort.

  • Put a time limit on how long you will talk to someone. My personal rule of thumb was that I would seek a phone call as soon as possible. Yep, same day if I could. I didn’t want to get on the phone without some small amount of chat, but I certainly didn’t want to spend days and days IM’ing with someone. A quick phone call will tell you immediately if there is any rapport. Make the call when you are going somewhere so you have 10 or 15 minutes available and then have to go – this will give you a good reason to get off the phone and save you getting stuck on the phone with someone you don’t like. If you like him, arrange another call asap.

  • Know who the guy you want to meet is, and write your profile to him. If you’re profile is too generic you’ll get every Tom, Dick and Harry responding. You need to feature things that your particular guy will respond to, and include qualifiers or challenges that will weed out unsuitable guys. Engineered.

Playing the dating game is a bit like running a business – you need to be smart and time efficient to keep it in perspective and get the results you want. This can be difficult when it’s such an emotional field of play. But the good news is that a lot of it is just common sense, and is generally a lot of fun!

So if you don’t want to wait for the guys anymore, get cracking!

Stephanie Chan is a Sydney based Life Coach, Dating Coach and Presenter.

Her passion is in working with people to improve self-worth, confidence & strength in all areas of their lives.

For daily tips, articles and insights, follow Steph on Facebook

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