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I’m Too Shy to Ask Her Out. What Should I Do?

I’m Too Shy to Ask Her Out. What Should I Do?

I’m Too Shy to Ask Her Out. What Should I Do?

You know the feeling.

You just met a woman that rocks your world.

She’s rented up a nice luxury suite in your brain and isn’t going anywhere anytime soon.

Naturally, you want to ask her out. But fear — ever the cockblock — makes that impossible.

This isn’t the first time fear has won, but now, finally, you’re endeavoring to make it the last.

So how do you “wipe the slate clean” ensure that sweaty palms won’t prevent this from happening again?

Perhaps you’ve thought to yourself; instead of having all these knots tied up in my stomach and living with anxiety and regret by myself, I should go out and meet people and practice getting better at asking women out/flirting/dating. But then when the time comes, you just can’t seem to muster the courage to pull the trigger.

You know you want something more out of life.

Specifically, you want her.

Avoiding the fear-inducing obstacles that stand between you and romantic success convince you to seek refuge elsewhere. Claiming “I’m too shy to ask her out” you instead opt for comfort in video games, Netflix, and mindless IG scrolling. 

This my friends, is emotional avoidance.

The negative feelings elicited from being rejected are literally painful.  That’s the reason emotional avoidance may be a factor in why some people avoid putting themselves out there and one of the biggest obstacles to finding and attracting the woman of your dreams. We know that emotions can influence dating habits, and that may get in the way of long-term relationship goals.

You’re here because you’re finally ready to address those emotions and reign them in.

We’re here to help.

“I’m Too Shy to Ask Her Out”… Here’s Why

We Numb Ourselves to Avoid Difficult Feelings

Be honest.

The only time we experience the negative is when we turn on the news.

But just as easily, we can turn it off.

We can flick, click, and swipe away from the negative anytime we’d like.

We live in a world the promotes well-being — at least at a superficial level. Our SM profiles are full of only life’s most positive highlights. No one ever posts about how they’ve been struggling with the loss of a friend or how they didn’t get a call back to yet another job interview.

We carefully design our lives in a way that allows us to artfully dodge emotive situations.

It’s this meticulous avoidance that leads to the improper development of emotional intelligence.

When we finally are asked to deal with an awkward situation, we collapse. We look for the nearest exit and sprint. If there isn’t a door around we drown in our ineptitude.

I don’t tell you this so that you think all is doomed and never download a dating app again.

Rather, by acknowledging this I hope to convince you that you’re not alone. That many Americans feel lonely and have a fear of asking women out stems from emotional avoidance promoted by our society.

So let’s address this.

Find Comfort In Discomfort

We avoid discomfort because we can’t tolerate it.

The key to overcoming a fear of rejection is to be able to sit with that fear, to look it in the face, and even eat dinner with it, perhaps even share an ice cream afterward.

But you’ll never conquer fear if you never ask it out.

Look, there is no single lifehack that can immediately strip you of fear. In fact, if you’re going after the complete eradication of fear you’re out of luck; that doesn’t exist.

And even though the self-help gurus like Tony Robbins might persuade you that fear can be done away with, it can’t, and it shouldn’t be.

What we need to focus on is living with fear and becoming familiar with it. It’s through this familiarity that we’ll be able to manage it and live life with fear as a companion rather than a nemesis.

On The Other Side Of Fear Is Magic

Turn fear into your wingman.

Realize that when in the context of romance, fear is the precursor to magic.

For example.

You’re on a second date with Michelle, a woman you met on Hinge. You’ve been enjoying your hike through Twin Peaks and are now watching the sunset. You suddenly feel the urge to kiss her.

A kiss that would solidify your feelings and accelerate your relationship. But the second that thought pops up, so does fear. The fear that this isn’t the right moment, that you’re not the right man. On the other side of fear is magic. The magic of a first kiss and the certainty of mutual feelings of affection.

Ya see, fear is a signal of awe-inspiring awesomeness.

Asking a woman out, a first kiss, asking a woman for her number, asking her to marry you -all these events are invariably coupled with fear.

When you feel fear creeping up on you, it should signal that something amazing might be about to happen.

The only person that can get to the other side of fear, is you.

Shift To A Growth Mindset

Changing your mindset from, “I’m too shy to ask her out” to “she’s dope, I’m asking her out right now” isn’t an endeavor to be completed over the span of a weekend.

In your journey towards changing your mindset, you’ll inevitably encounter hurtles. Encountering one and performing in a less than satisfactory way isn’t a failure — it’s expected.

The moment a negative thought pops into your head, realize why it’s happening. Chances are, if you’re about to ask her out, you’ll be fearful because something you care about is about to be challenged.

When you have a growth mindset, you’re able to see these emotions as a sign of awesome things to come. Moments of fear are moments of potential.

Transitioning into this mindset only works once you’ve made the conscious decision to make address your fear, your goal. Being aware of your goal and decision to better yourself will imbue you with the confidence and willpower to stay the course. By analyzing your objective, you’re more likely to complete it because you understand the consequences of achieving it.

Baby Steps

Many a motivational speaker would tell a man in your situation to just go for it.

To dive headfirst into the deep end and get rid of your fear by asking out as many women as possible the next time you’re at the gym, bar, or party. Through brute force exposure, you’ll overcome your fear.

While this may work for some people, for many it doesn’t. The chief reason being — it’s too terrifying to execute.

Imagine going to a bar right now with the task of asking out 3 women. Chances are you won’t do it.

This is why your homework isn’t to dive headfirst into the deep end and shatter both your ego and neck in the process.

Rather, we’ll dip our toes in.

First, you’ll want to understand your comfort zone.

Where do your boundaries of comfort end? Are you fearful to greet a woman passing down the street, or are you more than comfortable chatting it up with strangers, but simply struggle to pop the question of, “will you go out with me?”

Once your boundaries have been identified, it’s time to stretch them. And again, by stretching I don’t mean buying C-4 and completely blowing a hole in fear. Instead, think of your boundaries as lithe dough that you can shape if you invest enough time and care into the practice.

To apply this to asking a woman out, first practice the precursors to asking her out. Think of what comes before that and practice those fundamentals.

This might look like:

  • Chatting it up with friends of friends
  • Going out to a party with a couple of friends
  • Download dating apps and throwing out some opening lines
  • Crack a joke with your local barista
  • Talking — not flirting — with strangers at a bar

Slowly you’ll feel more and more comfortable with these fundamentals. As you gain confidence consistently push yourself just a little bit further. Remember that there is no time limit here. You don’t need to go from 0-100 in a week. Take your time. The only thing that matters is that you keep progressing.


You never want to go into a fear-inducing situation blind.

You wouldn’t walk into a job interview without having prepared first right? So why act any differently when asking a woman out?

After you’ve practiced the fundamentals it’s time to ready yourself for the big one.

You might prepare by visualizing what might happen in your head. Imagine walking up to her, chatting, and then popping the question. Imagine what you’ll say, how it’ll sound, and how she might respond. Think of the many twists and turns this conversation can take. In this case over-preparing is a good thing.

Ideally, you practice with a female friend before asking her out.

Let Go Of The Safety Net

This is the moment you’ve prepared for.

The meeting ended and the day is over. You see her break off from a group of co-workers and is headed to the parking lot. Now’s your chance.

It’s time to get rid of the safety net. To take off the training wheels, to peel off the floaties and just go for it.

Every meaningful gain only comes because you took a risk.

Before you take the plunge, be aware of how ready you are. Go over your plan and remind yourself that there is magic on the other side of fear.

The romantic date nights, the sex, the family, the vacations to Cancun and Rome. It’s all there waiting for you. You need only to decide to take it.

On To The Next One

The worst-case scenario is that she says no.


But be honest with yourself, was it really that bad?

Odds are your ego didn’t shatter and you were able to walk away with your dignity — unless of course you started bawling Tom Haverford style.

The next step in your journey towards leashing fear is to continue to ask women out.

You can do this with the help of MegaDating.

After rejection, you might wonder how you’ll ever find another woman worth asking out.

Don’t be dramatic.

There are amazing women everywhere, you just need to search for them.

Love isn’t something that creeps up on you. Rather it’s out there, you just need to find it. Find these women by downloading dating apps, sparking up convos with women at parties, asking out your teammate from an adult co-ed sports league, get set up through a friend, meet someone with a shared interest at a Meetup event, etc.

Interacting with new women should be easy if you’ve altered the comfort zone by practicing social fundamentals.

But hey, if you still don’t feel comfortable there’s always another option.

Team-Up with a Coach

It’s difficult to go it alone.

Constantly climbing a mountain that you feel you’ll never summit can invite failure.

To increase the chance of success, team up with guys in similar positions.

Our group coaching program involving 6-10 guys all awkwardly fumbling through the dating scene can be super motivating and provide you with the support you need to keep moving forward.

The group is called Datehack.

In this group we’ll address everything from what women think in the midst of a date, to how to get her to respond online, to how to respond if she flakes on a date.

After 3 months of weekly 90 minute sessions, you’ll know how to escalate sexual tension, be able to flirt with any woman, and of course will be well on your way to finding a girlfriend.

But hey, we realize that some guys are too busy to attend a dating class. That’s why we offer busy, yet romantic men, matchmaking services. Through our team of e-recruiters, we’ll find you compatible single women in your city.

To get started, book a 1-on-1 Zoom new client session with yours truly.

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