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Valentine’s Day Edition: A Bachelor’s Guide to Landing A Date Anywhere, Anytime

Valentine’s Day Edition: A Bachelor’s Guide to Landing A Date Anywhere, Anytime

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In the spirit of Valentine’s Day, this is a guest post by a professional dating coach.

It happens to the best of us. Somehow, you and your awesome self has wound up single this time of the year. Before you settle yourself in for a tub of Miller Lites and Baconator sandwiches, have you wondered what it’s like to take your dating fate in your own hands?

Reflect on this scenario: You are at a coffee shop, a bookstore, or strolling down the street. Out of the corner of your eye, you see her. Not more than a few feet away, the beautiful stranger. She is mesmerizing. The girl of your dreams, really. She glances over and makes eye contact. She smiles. Your heart jumps out via your throat. You suddenly find it conspicuously difficult to breath normally. You should probably go over there and say something. But no, what if you fu*k it up? You scourge your mental repertoire for something to say- but your usual confident, spontaneous self is at a loss. You twiddle your thumbs some more. And without warning, just as quickly as she appeared, she is gone, no doubt off to find some one with more grit. You kick yourself in the ass. Where is that Baconator?

Has this happened to you? Random encounters that you wished you acted on? (As for me, I’m happy to report that my dating life is nothing short of flawless. A bevy of women always manage to find my phone number and offer themselves to me… oh wait, I’ve lapsed into fiction)

Dating coach Stefan Hall has an answer to our plight. Hall’s company, Lifestyle Transformations, focuses on helping men improve their dating lives through healthy, holistic self-improvement. He and his team has coached hundreds of men across North America on becoming more socially adept with the often allusive opposite sex. He has been featured in various media outlets and has held seminars for thousands. His claim to credibility? Stefan speaks from the experience of having approached and interacted with more women than anybody else in Vancouver.

Enter Stefan Hall.


The Makings of a Dating Coach

Tony asked me to contribute to his blog as a “dating expert”, and to provide some useful tools on how men can have consistent success landing a date whether they are out for a walk, at the grocery store, bookstore, wherever. While I’m flattered to be known as a “dating expert”, it was never like that for me several years ago.

In fact, I can still remember my high school days as a guy who was rather “clueless” with the opposite sex.

I know exactly what it feels like to have a crush on the cute girl in school, but being terrified of asking her out. I know the dreaded “Friend Zone” far too well.

For the longest time, I blamed my lack of success on being too shy, not good looking enough, or for not being something-outside-my-control enough.

So I did what any sane man would do: go out and talk to literally thousands upon thousands of women. I approached them everywhere: coffee shops, malls, nightclubs and bars. What I learned from these experiences was that becoming successful with women and dating is something that is learnable. It’s a skill, just like anything else.

Today, I reap the rewards of years of developing myself. I’ve gained the ability to be able to walk up to and meet almost any woman that I want to. I can go out any given day of the week, it doesn’t matter where I am, and leave with several phone numbers and dates lined up.

I’ve spent years learning and tweaking my approach, so that you don’t have to. To write about what I’ve learned from my experiences would fill books and is beyond the scope of this post. However, let’s start off with the top three do’s and don’t of asking a women out:


i) DON’T TAKE VALUE– Don’t approach people with a hidden agenda or focus on what you are going to get in return. Thinking about how you are going to get their number, get them to go on a date with you is selfish and often impedes the courtship process.

ii) DON’T HIDE YOUR INTENT– Don’t hide your feelings, or let your fear or anxiety take you over . Man up and communicate your interest in that person you want to meet or are interested in.

iii) DON’T BE A CREEP– Some compliments can be received as weird or creepy. Avoiding the creep factor is about making the person feel comfortable. If I just came up to someone and said ‘hey baby, what’s up?’, they probably wouldn’t talk to me again.


i) DO ADD VALUE– Think about how you can improve her day by talking to her. Change your mentality from being a go-getter to a go-giver. What woman doesn’t want a guy to make her smile or make her feel better about herself? When you see someone you want to meet, think about how you can add value to their life. Think about how you can make her smile, or make her feel better about herself.

ii) DO STATE YOUR INTENT– Let her know you are interested right away. Don’t hide your intentions.

iii) THE OBVIOUS– Be authentic. Do not rely on key phrases or pickup lines, instead be confident, genuine and let your personality shine through. If you can just be real and true and honest, women appreciate that a lot more than anything else.
THE NOT-SO-OBVIOUS– Be focused on being more rather than doing more. Most guys are focused on doing, concerned with the thoughts of ‘what can I do to make this girl like me’ or ‘what should I say”. Instead, focus on the big picture. Ask yourself how you can be a better person, how you can be more social and charismatic. Are you building an interesting life for yourself? Focus on developing better communication skills and ultimately, how to become a better man. That is the long term learning plan.

Valentines Day Edition: A Bachelors Guide to Landing A Date Anywhere, Anytime

The Breakdown of a Good Approach

Now that we’ve covered the basics of becoming more rather than doing more, here’s is a breakdown of a typical approach that you can start using immediately. A caveat: let the below sequence be a guideline, not a straitjacket. Every women and every interaction can be different, don’t fall into the trap thinking there is some holy grail checklist that you have to run through to ask a girl out. Don’t be that “weird” guy.

1) The Pre-Approach: Cultivating Instant, Unstoppable Confidence

Ok, so you see a woman you want to meet, but have this “approach anxiety” that consumes your entire body. Don’t get me wrong, asking an attractive woman out during the day can be scary. You have neither the support of alcohol (or do you?) or the egging on from your friends as you would if you were in a nightclub or a bar.

Common nagging thoughts:

“What am I going to say?”

“What if she has a boyfriend?”

“What if she rejects me?”

These thoughts cycle through your head. The two biggest things you can do right away to override this inner dialogue is to:

a) Change Your Focus

Change your focus to, “How can I make her smile?”, or “How can I add value to her life?” or “Why am I so amazing?”. Men tend to live inside their heads during a conversation with a woman they are interested in. Instead, live in the present moment. Focus on her hair, her smile, her eyes and what she is saying. When you change your focus to something more empowering, it will radically change how you feel.

b) Change Your Body Language

Every emotion you experience manifests through your body. When you’re nervous or have anxiety, it shows in your body language. Conversely, if you immediately change the way you’re using your body, you will immediately change the way you feel.

Someone who is nervous and lacking confidence will be slouched over, have poor eye contact, shallow breathing and talk in a small voice. Don’t be that guy. Instead, stand up tall with your shoulders back. Smile like you mean it. Breathe deep from your chest. Project your voice. Make eye contact. And loosen yourself up! Be in control of your body language, and your confidence will follow.

c) Be Your Best

This means looking your best and feeling your best. Dress well and take care of yourself. You don’t have to go overboard but don’t be a slouch. Ketchup stains on your wrinkled dress shirt says a lot about your character (or a lack thereof). If you are not already athletic, join a gym or find a physically challenging sport and stick with it.

Valentines Day Edition: A Bachelors Guide to Landing A Date Anywhere, Anytime

How you look say A LOT about you.

2) Approaching Her Anytime, Anywhere

When you’re feeling confident and having fun, the approach is easy. Somethings to keep in mind:

Be Upfront with Your Intentions: Most women are incredibly astute social creatures and can size you up before you even open your mouth. If you say something that you do not mean or act in a way that is incongruent to who you really are, she will pick that up straight away. That’s why, being genuine and authentic goes a long way. I always let a woman know I am interested in her within the first moments I meet her.

Use a softener: Always make a woman feel comfortable if you are going to approach them especially if you are approaching them in a random place, like a coffee shop, where women are probably not expecting to be approached in such a direct, open manner. A softener is a statement that honours the reality of the situation and instantly puts both of you at ease. For example, if I come up to a girl sitting in a coffee shop, I might say something along the lines of “Hi, I know this might sound a little bit odd, but you have a great smile and I wanted to meet you. I’m Stefan.” You want to do everything in your power to make her feel comfortable.

Here are some simple things you can say when you want to approach a woman:

“Hey, this might sound a bit off, but I noticed you and had to say that I think you’re gorgeous. I’m Stefan.”

“Excuse me, this might sound a bit random, but you look amazing. What’s your name?”

Generally, any sincere compliment or means of adding value works great. The key thing is to make her feel comfortable and make her SMILE.

Remember, it’s not about what you say. The words aren’t really all that important. It is underlying assumption any man with the cajones to walk straight up to an attractive women in broad day light and ask her out is worth at least a second look.

3) Sparking Attraction… by Having a Normal Conversation

Once you’ve started the conversation, you need to spark attraction and build chemistry. Too many guys make the mistake of jumping the gun and going for a phone number right away. Even if a woman likes your first impression, she still needs to feel comfortable enough to exchange contact information with you. At the risk of sounding obvious, she needs to have a sense of chemistry with you.

While there are many ways of doing this, one of the best ways is by getting her laughing. My favorite way is by playfully teasing her in
the conversation.

That means I might playfully accuse her of being a troublemaker, or by misinterpreting what she’s saying and tell her “We would never get along… you’re probably a player and will try to take advantage of me.”

The key is being PLAYFUL, not mean, and to show your confidence and how comfortable you are in the conversation.

The moment you get her laughing and having fun, she will associate those positive emotions to YOU. So, be fun in your conversations with her!

4) Get Her Phone Number

Once you’ve been talking for a while, it’s time to find a way to reconnect. During the daytime, women are often on their way to something, whether it is back to work or to run an errand. Therefore, it is important to be understanding and find a way to bridge that time gap between now and when you’ll see her again.

When it comes to getting the phone number, you never want to ask. You always want to ASSUME that she wants to give you her phone number.

So, to give you an example, you could say: “Well, it was nice meeting you but I have to get going now. Do you have a cell phone?” You are not asking if you can have her phone number, you’re asking if she has a phone and ASSUMING she is going to give it to you.

It’s important to follow up quickly. As the saying goes, “Strike the iron while it’s hot!” Forget the 3-day rule. Call her the next day.

Make sure you’re prepared to set up the date and know what you guys can do together. Always, always have a plan.

7) Repeat Step 2 Until You Get A Date

As you’ve probably realized by now, there is no magic bullet. The more you do this, the better you will get.

At first it can be challenging or uncomfortable, no different than learning any other new skill. So yes, it does take practice.

Start actively living a social life. Make conversation with everybody you meet on a regular basis, whether it be the grocery store cashier, the bank teller, or the guy who works at the convenience store across the street. It doesn’t have to be anything special, maybe the weather, or a local happening, just make an effort to be a REAL person.

This is not just for asking women out. Friends, business contacts and other important people will come into your life easier if you bring a positive, comfortable energy to every interaction you have. You have to learn to become comfortable being social, and the rest will follow.

Wishing you success and fun for your Valentine’s Day!


You can check out Stefan Hall’s dating company at www.LifestyleTransformations.com and his blog.

About the Author


Wants to explore the world, write about it, and inspire others.


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