2 Tools to Help Shy, Single Men Approach and Talk to Women

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Approaching a woman with the intent of starting a conversation can be paralyzing for a shy, single man. There are thousands of tips about what to say to women – so what’s really holding a shy man back?

The real challenge so many shy, single men have when it comes to meeting women begins with their hidden inner blocks and beliefs.

Dr. Neil Fiore has written a great book called, “The Now Habit: A Strategic Program for Overcoming Procrastination and Enjoying Guilt-Free Play.” While this book is by no means focused on the topic of dating, Dr. Fiore’s strategies can be applied to help even the most shy, single man get out of his way so he can consistently approach and talk to women.

How can the principles of this book on procrastination help a shy, single man overcome his fear of meeting new, remarkable women? Let’s take a look.

Tool #1: Have an unwavering sense of worth

“People do not procrastinate because they are lazy or irrational. They procrastinate because it makes sense, given how vulnerable they feel to criticism, failure, and their own imperfection” – Dr. Neil Fiore, 2007

This tool is based on Dr. Fiore’s principle that your worth as a person doesn’t need to be tied to your results (…or your relationship status) (Fiore, 2007).

If you can manage to separate your value as a person from your relationship status (or any other result you’re after) then speaking with women you’re attracted to will be far less threatening. This way, if your conversation with a woman flops, your happiness and dignity no longer have to be at stake.

The challenge for many of shy men (and for must of us humans), is that they take the opposite approach – it’s common to be their own worst enemies. When a shy man does or says something less-than-perfect, he tends to harshly judge himself and then repeat cruel things to himself that he would never say to a person he even strongly dislikes.

When it comes to talking to women, why not decide to be your own best friend or gentlemanly ‘wingman’ instead?

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Here’s a helpful phrase (based on Dr. Fiore’s principles) for you to make a practice of affirming to yourself (especially as you approach a woman you’re attracted to):

“I’m just going to start a conversation with this woman. I’m not trying to prove anything to anyone about my worth – I’m just going to talk to her.”

Once you get the fact that your value as a person is independent of your relationship status, it’s time for…

Tool #2: Focus more on starting and less on ‘closing’

“The last time you start is when you will finish. You’re only focused on starting, which is a clear image of when to start, where to start and what to start. That’s what you want to do.” – Dr. Neil Fiore, Time Experts Telesummit

It’s common for a shy, single man to believe he’s doomed to remain single because he doesn’t understand all of the complexities and details surrounding women and relationships.

The downfall of this way of thinking is that many shy men get stuck endlessly putting this area off. A more helpful way would be to get started with small, manageable 15-30 minute ‘chunks’ while remaining curious, consistent and open to learning and applying relationship strategies as you go (Fiore, 2007).

Here’s an example of a fast way for you to get started on this bigger goal of learning how to authentically attract and then date a genuine woman:

• Choose a time today, to set aside 20 minutes to write down the top three values and life-goals that you want to share with a woman.

• Tomorrow, after dinner, brainstorm five places where you might find the type of woman who would share these values (ex. yoga studio, cooking class, aerobics class, etc)

• The day after that, ask 3 women you’re already comfortable around, the following question: “What would be (or has been) a question or conversation-starter that was so interesting, that you would honestly start talking to a random, mediocre-looking guy who had just approached you?”

• The day after that, choose a time to go to one of the places from step t and when you see a woman you’re attracted to, simply walk up to her, say ‘hello’ and ask her one of the questions/conversation-starters you came up with.

• Afterwards, celebrate, having done this no matter what the result, by giving yourself a reward that you’ll enjoy (example: a drink with a good friend).

• For the next 30 days, continue to ask yourself: ‘What 15-30 min action step am I going to commit to today that will get me moving towards sharing my life with an awesome lady?’ Then follow through with each of your actions.

Can you see the benefit of turning the bigger aim of building a relationship with a woman, into a methodical series of smaller steps?

Plain and simply, focusing on starting with small steps will be more enjoyable and more realistic than the frantic spiral-effect of thinking in huge increments like, “I must find and date the perfect woman so I can spend the rest of my life with her!”

That sort of panicked-mindset is stressful and leaves a person with no idea how or where to start – it also makes it unlikely that you’ll consistently meet women because other attention-competing activities like eating, playing videogames or just about anything else will ‘win’ every time. (Baren and Fiore, Time Experts Telesummit)

The real downfall of not treating the experience of meeting women calmly and intentionally is that you’re more likely to find yourself single 1, 5…or 10 or more years from now.

Wouldn’t it be more rewarding to make dating and meeting women easier on yourself?

By applying Dr. Fiore’s simple principles don’t be surprised if you find yourself starting earlier and with more gusto on even the seemingly most daunting life goals…like dating an awesome lady!

For today, what important 15-30 minute, dating-related task are you willing to commit to starting … without worrying about finishing?

Please leave your answer in the comments below

Works Cited:

Baren, B. & Fiore, N. Ph. D, http://www.timeexpertstelesummit.com

Fiore, N. Ph. D. (2007) “The Now Habit: A Strategic Program for Overcoming Procrastination and Enjoying Guilt-Free Play.” New York: Penguin Group.