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

Showing 4 comments
  • Jeremy Boyum

    all I can say is, yes

  • Jeremy Hasson

    Hey Nate! Nice article, I always appreciate your words of inspiration. You have a natural ability to encourage growth in people and I hope to learn from you. I hope you are doing well, and that you wouldn’t mind if I gave some constructive feedback. I was a little thrown off by some of the things you mentioned in your article, like the idea of less aggressive or ‘masculine’ men being labelled as this “pussyfoot.” I feel like the expectation of men to live a life of ‘risk’ and ‘danger’ is unfair to men and women. Men shouldn’t all have to abide by the ‘alpha male’ mentality, and women shouldn’t be punished for not being interested in a man. I’ve read a lot about how the concept of the ‘friendzone’ is also problematic because it does not allow women the choice to say no without being bashed. What are your thoughts on women sharing the responsibility to court their partners? After all, not all relationships are between one man and one woman. And where does this ideology leave people in same-gender relationships? Thanks again for continuing to do great work, and I hope we can have a productive, inclusive dialogue about the very important issues of gender and sexuality. -Jeremy

    • Nate Hilpert

      Jeremy! Thank you so much for writing in, man. I’m honored that you took the time to read this 🙂
      Thank you for the compliments and encouragement, my friend!
      I appreciate your constructive feedback, and I hope we can have an awesome dialogue as well! I apologize for my delayed response.

      Ahhhh, yes…the “pussyfoot” comment, haha. I knew it would snag some people. I had a great time crafting the metaphor, and after I was done and stepped back, I knew it was a bit ‘pointy’ as I call it, lol. So, the point of the article is not to promote the machismo idea of manhood. I’m actually super anti-steroid, -workout-till-you-die, -go-hard-or-go-home, -nothing-but-sex-and-anger kind of attitude. I have a completely different idea of manhood. What I’m trying to promote in this article is risk-taking when it comes to asking an attractive partner out. I believe that part of being a man is taking risks…it seems to be hard-wired in us. I mean look at an average three year old boy: he’s sliding down railings on staircases, blowing legos up for breakfast, and intentionally seeking out dangerous situations. I don’t have any hard science for this, but it seems to be in our nature as men to take risks and to be dangerous. Part of that is an innate desire for us to know whether or not we can come through when it counts. This means when all your chips are at the center of the table and you’re all in, we as men want to know that we can make the play, win the girl (or whichever heroine gender of choice), and save the day. All too often, I see men stuck in a phase of being afraid of asking someone out because they want to “make sure she likes me”. And that causes them to be stuck in this guessing game obsession that’s sickening to watch from the outside and maddening to experience from the inside. There’s no harm and no foul in going up to someone you’re attracted to and saying, “I think you’re stunning, and I would love to get to know you more. May I take you out on a date?” Moreover, I think there are so many character benefits to stepping outside of your comfort zone, facing your fears, and taking risks. It’s nothing to do with “being the muscle-head, aggressor, macho douche”. It’s everything to do with getting in touch with the deep desires of your soul–to see if you’ve got what it takes to come through when it counts…which takes risk…and it takes danger. And hopefully, it turns out for the better. Either way, you’ll be building character and not getting stuck in the sickening cycle of “she loves me, she loves me not”.

      Now, as far as women not being punished for not being interested in a man, I 100% AGREE with you. The beautiful thing about a man asking a woman who is NOT attracted to him out is that she has the opportunity to be appreciated and gracefully reject the suitor. There’s finesse in rejection. Sandwich the rejection between two compliments like “I think you’re so brave to walk up to me, and I’m so flattered that you appreciate me enough to ask me out on a date. However, I am going to decline your offer. Thank you again!” I am all for women accepting/declining offers based on their whim. Absolutely 🙂

      Now, as far as the friend zone is concerned, I’m hoping that men will avoid this altogether by stating their intentions clearly up front instead of whisker stepping around with their affections concealed and their intentions askew. Because most of the time, the “friend zone” is actually the fault OF THE MAN. He’s posing as a friend, but underneath that, he’s really just waiting for the opportunity to get close enough to ask her out…or bide his time while he accumulates the confidence. And when he asks her out after reading way too into her non-signals because he’s looking for some excuse to believe she likes him, he rages because he’s “wasted” all that time. Truth is, if he just asked her out in the first place, he’d probably have a better chance of dating her in the first place, AND he wouldn’t have to disguise his friendship until she’s vulnerable enough to pounce. This way, if he chooses to continue in a friendship with the girl after being rejected, at least there’s clarity on where he’s at…he obviously likes her, and now she knows that as she proceeds in the relationship as she pleases.

      My thoughts on women sharing the responsibility to court their partners…interesting question…one I haven’t given much thought to. Personally, I prefer in my relationship to be the courter. I believe that men are wired to go after a beauty and rescue her (or insert whatever preferred gender of beauty here). And I believe that women are wired to have a beauty to unveil–they want to be seen as captivating. Most of these observations I’m citing are from a book called Wild at Heart and Captivating by John Eldredge. It’s a fascinating read (do note it is geared primarily towards a Christian audience; this doesn’t knock any of the fascinating findings; however, the solution to the problem Eldredge discovers is leaning into one’s relationship with God). Because of the way I believe men and women have been wired, the most natural way to speak to their soul is to have a situation where men can go and rescue their beauty, and women can unveil their beauty and be captivating. Now, this doesn’t mean she’s a damsel in distress by any stretch of the imagination, but women are notorious for their beauty…I mean throughout history, the women figure has been catalogued in art and sculptures and paintings drastically more than the male body. So, I lean towards the more traditional suitor dynamic. (Of course, if someone else has a different bent or preference, that’s absolutely their liberty to decide!)

      So for same-gender relationships, I’m not too well-versed on the dynamic. I do know that Eldredge mentions in the book some interesting postulations about homosexuality for men. He notes that all men have a “core wound”–typically inflicted by their father. This means they’ve had a void of affirmation that they have what it takes as a man. They haven’t had a masculine figure beget their masculinity. And because of this, men go and search for that validation elsewhere. In Wild at Heart, Eldredge notes that homosexuality is a logical step to take with that wound because the idea would be to seek that masculine validation from a male partner. Now, of course, depending on where you are on the pre-determined sexual orientation scale, this postulation might seem preposterous. And that’s ok 🙂 I just thought it was fascinating! Someone very dear to me in my life is engaged to a man, and from what I’ve gathered from conversations and observing their relationship, homosexual relationships don’t really have clearly defined “man” and “woman” roles. Some do! But some don’t. In this particular couple’s relationship, they both take on aspects of the stereotypically divided gender spheres. At the same time, those stereotypes are also blurring in heterosexual relationships…for example, for military wives, they assume the “head of household, alpha presence” you were referring to because they’re the only adult there until daddy gets back. So, I think a lot of the gender dynamics within homosexual relationships just depend on how the partners opt to align themselves.

      I hope my response piques your intellect as your questions did mine. I look forward to hearing back from you, Jeremy!

  • Tommy

    You don’t realise how good of friends you guys are! Sounds crazy bro but you literally changed your mates life! He now has the confidence to ask girls out! You lads are top! I’m only 15 so this going to pub business doesn’t really relate to me, I only came to have a look at this stuff because there’s a girl I really like at school… I’m sure you’ve heard it all before! My problem is that I’m crazy about her! To the point where I’m looking at her profile like some obsessed old man and I’m searching crazy shit like this! (This article is sick! You get what I mean by that) just I honestly don’t know how to tell her about my feelings! It’s all good me sat here telling some people who Iv never met but I can’t tell her! I’d rather tell everyone but her

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