Freaking Ask Her Out Already

“I’m too chicken! I don’t have the balls to do it!”

He wailed into his hands as they shielded his face from the invasion of embarrassment he felt encroaching around him. He just took a bet and lost, and he knew the wages would make him look the absolute fool.

My friends and I sat there and laughed. And laughed. And laughed.

We hunkered in a corner booth at a hotdog joint downtown for his 21st birthday. We ate and drank and joked, and all the while, birthday boy had his eye on our cute waitress. He was making her laugh and flirting her up, so I nudged him and said, “Dude…freaking ask her out already!”

He shook his head, stomped his foot, and swore he wouldn’t. So, I decided to make a bet with him: “How about this…if she’s from Michigan like you, then you have to ask her out on a date.”

And as a betting man, he played his percentages well. We’re in Texas, 1400 miles southwest of Michigan. We’re on polar opposite halves of the north-south divide of the U.S., so chances were, she shouldn’t be from there.

With his hand in mine, we had a deal, and the night raged on. As the alcohol consumption continuously increased, so did the amplitude of our boisterous conversation. By the end, we were hooping and hollering, and as we were winding down our meal, I called the waitress over, told her how to divide up the check, and popped the question.

“Yeah, actually, I am from Michigan. That’s a strange thing to ask me though–how come; what’s up?”

After she left, my friend immediately burst into sorrowful woes and the rest of us into side-splitting laughter.

We watched him wrestle with the prospect of his punishment. He hadn’t made a habit of asking out attractive women he didn’t know from Eve. It was miles from his comfort zone and felt more like he was laying his head out on a chopping block and asking for someone to drop the guillotine. She was out of his league, and we all knew it.

As the minutes dragged by, the dread began to billow in his gut, and he continued squirming as we described the reality of his pending punishment. He couldn’t take it anymore, so he stood up, took a deep breath, and puffed out his chest in faux confidence. “I’m going to do it,” he declared.  As we watched him, we simultaneously cringed and laughed quietly to ourselves as our friend was led like a lone sheep to the slaughter.

“Well…?!” We said in unison when he returned with a big grin on his face. He left us in looming anticipation as he kept the news to himself until we cleared the front door threshold and earshot of the restaurant.

He turned around to face us and said, “She said no.” We all smiled and groaned with him as our expectations were confirmed. “But,” he interjected our laugh-moan and continued, “she said it took a lot of guts to come up to her and ask her out. She thinks I’m kinda cute, and she added me on Facebook so she could hook me up with some of her friends.”

And the heavens rejoiced. We all cheered uproariously. It was like he won the Super Bowl or something. We slapped him on the chest and gave him a round of high fives, fist bumps, and slap-asses each.


The coolest part of his victory is that he did something most men nowadays don’t do.

Scientifically, if we were to chart the recent course of the evolution of man, we would see that something has gone terribly wrong over the past decade. Their feet seem to have sprouted fur, and they are beginning to resemble the form of felines. At this rate, if they keep avoiding women they’re attracted to, they’ll be coughing up hairballs that are more real than the pair between their legs and forever be doomed to a new species of pseudo-man called the pussyfoot.

Risk is a part of the DNA and design of the soul and heart of men. And somewhere along the way we seemed to have lost touch with that about ourselves. Instead of embracing risk and facing danger head on, we nestle into the comfortable “make sure she likes me” phase for many miserable weeks. Then one day, we wake up from this ego-preserving hypnosis and realize we’ve crossed the point of no return in the place where all attraction goes to die: the friend-zone. We trade risk of rejection and momentary sadness for a long-term I.V. of cowardice that slowly sucks out every drop of confidence we had. Over time, we shrivel into this brittle, wrinkly, shell of a man who has been reduced to some puppy-dog obsession over a woman that now forever sees us as her nice, timid little brother.

Have you ever caught yourself checking a girl’s Facebook or Instagram several times a day to see what she’s posted between now and an hour ago? Have you asked friends to help you decode the love encryption she probably didn’t embed into the last status update she posted? Have you texted her one, two, three times after she didn’t respond to your last text?

I have. There’s no shame here in what we’ve done in the past. At one point, we all fear rejection because it stings. But it’s time to acknowledge there’s got to be a better way to doing this. We’ve got to try something different than creeping social media and sinking into sadness when she doesn’t give you the affirmation we all so desperately want. Because the fact of the matter is, there’s a better way. But it’s not without risk. It’s not without danger. It’s not without fear. However, when you choose to act in spite of all of that, you not only avoid the senseless self-pity, but you actually come alive.


You weren’t created to coddle your keyboard and count your crows as the cowardice overcomes your confidence. You were woven with wildness in your heart. And when you touch that part of your soul, you’ll feel a rush that well-outweighs the risk. 


The best part of my friend’s story was that the waitress actually wasn’t from Michigan. When he went to the bathroom, we prepped her to tell him she was. And even though my friend got rejected after this dubious omission, he was beaming uncontrollably because he felt his heart beat in that crazy fast way it does when you face your fears. He wrapped both of his arms around danger and wrestled it to the ground. He jumped from comfort and splashed into the adventure below. And when he surfaced, even though he didn’t get what he sought, he got something better: the rush of his heart fully alive.

So take this as a challenge–not from me but from your heart. Because it longs to reunite with the wildness it was created for. And who knows? You might just be the knight to rescue your princess because you risked it, followed your heart, and made the climb.


Cover Photo Credit: Flickr Creative Commons

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