The 20 Strangest (and Borderline Insane) Headlines I’ve Written in the Past 3 Years

Cover Photo by Gratisography from Pexels

With their context, why they’re strange, and how to make them work in 2021

As I was thinking about the fact that I had been awake for an hour and hadn’t gone to pee yet, I was reminded of the strangest headline I had ever written publicly: “I Forgot to Pee This Morning.” I guess it’s proof that I used to have no filter in my writing (and still don’t?).

So, to celebrate my sometimes twisted mind and to give you a good laugh, I’ve compiled some of the strangest headlines I’ve come up with in the past three years. For each, I’ll give as much background as I can remember (hint: not much), and bash it because let’s face it, it’s bad — most of the time, embarrassingly bad.

Here goes…


1. “I Forgot to Pee This Morning”

That article came after being in my most intense state of flow I had been in at the time. I had accomplished so many things while paying zero attention to my surroundings or my physical needs.

Let’s be honest, it’s a crappy headline. How I got the courage to even write this is beyond me. We don’t want to hear about anything that comes out of anyone’s private parts. Ever.

I remember around the same time a writer I followed wrote a headline that basically said that he was taking on the challenge of not masturbating for a month. That’s worse than mine, but not by much.

2021 alternative: “A Concrete Example of Flow in Action and How You Can Replicate It”


2. “The Ultimate Regurgitation of Epic Info About Writing on Medium.com”

That article was written after I had assembled some of the best resources on learning how to write on Medium. I covered so many topics that I had no clue how to organize them.

“Ultimate Regurgitation of Epic Info”? Wtf? This sounds terribly unorganized (it was/is). And who uses regurgitation in their headline, and in a positive way at that?

That article actually received decent success, though I’m guessing it was because it had some of the best information you could find on the platform at the time.

2021 alternative: “A Veteran’s Tips on How to Get Started on Medium”


3. “OMG That’s What a Real Baby Looks Like, EWWW??!!!”

That was a fun one. It was actually a quote from Jessica Wildfire as a response to one of my articles about the birth of my son. I loved her reaction so much that I had to write about that topic.

Not all good quotes make for a good headline, however. This is borderline insulting for parents and for babies. I guess my audience were people who wanted a good laugh. Well, the only things laughing were my poor stats.

2021 alternative: “Babies Are Cute, Just, You Know, a Few Months After Being Born”


4. “The French Word for ‘Mistaken’ Sounds a Whole Lot Like ‘Trump’”

As the presidential elections between Trump and Biden were in full force, I could easily see that it was the hottest topic of the moment. Being a French Canadian, I was trying to figure out an original point of view on the topic. As I heard people say Trump in French, it made me laugh every time. It really does sound like the word mistaken in French.

So I made this the headline… expecting what exactly? “Good, I learned a new fact today,” said most readers. What was the point of this headline? Insult the current president? As someone who knows nothing about insulting people, I probably should have skilled up before.

2021: “Go Vote — Your Canadian Friend”


5. “Okay, I’m a Fraud. But So Are You Unless You’re Boring”

I don’t exactly remember the context of this one. I likely wrote this after I felt like I was writing about things that seemed beyond me, knowing who I was in the past.

My first thought reading this now is this: what? Like, what, what, what? Did I just call myself a fraud? And everyone else reading it? Or, I guess, only if you’re boring… for some reason? And who starts a headline with “Okay,”?

2021 alternative: “3 Ways to Showcase the Most Interesting Sides of Your Personality”


6. “How Taking Photos of a Naked Girl Strengthened My Marriage”

This wasn’t something I planned on writing about, but a friend dared me to, so I did. Back in January 2019, my wife and I were apart for six months because of her work. She lived in the Democratic Republic of Congo, while I was living in Colombia.

Long story short, I had done a portrait photo shoot of a friend the month prior, and after that, she asked me for a boudoir photo shoot, which I’ve always wanted to try. I was torn about whether I should tell my wife or not. Being where she was, it was hard to communicate, so I was afraid the message would be distorted somehow.

I ended up asking her if she was okay with it, and she gave me the most honest and kind answer one could wish for. We embraced that honesty and grew even more as a couple.

As for the headline, that was quite risky. “Photos of a Naked Girl” is probably not a very safe thing for a man to write about.

2021 alternative: “This is the Level of Trust Required for Relationships to Thrive”


7. “The Un-Epiphany Leading Me To Thrive In 2018”

I don’t remember the context for that one. I guess it came from my personal annual review. Maybe I noticed something so obvious in hindsight. I am, however, just speculating here.

Huh? What’s an un-epiphany? That sounds like the opposite of what I want. Also, who are you again?

2021 alternative: “How to Perform an Insight-Filled Personal Annual Review”


8. “Are You F-ing Serious?”

I don’t remember the context for this one. Maybe I’m overreacting to something. Though I have a suspicion that this was about taking things seriously and not so much about reacting.

If I’m right about my suspicion, this is definitely a misleading title. Also, was “f-ing” really necessary? I really don’t see who I was trying to attract with this.

2021 alternative: “How to Choose What’s Worth Taking Seriously in Your Life”


9. “If It’s Not in My Calendar, I Simply Won’t Do It”

I believe I wrote this after a streak of forgetting to do things that were written in my notebook as tasks to do. I realized that, unless I set a time and date when the task should be done, I didn’t follow through.

“Good for you,” thinks every reader. “I guess you want me to schedule things in my calendar? What if I’m not like you?”

2021 alternative: “If You Can’t Follow Through, Try This Scheduling Technique”


10. “15 Minutes Later… Blank Page. How Overthinking Diminishes Authenticity in Your Writing”

I believe this came after I had written for two months and finally hit my first writer’s block. Previously, I’d stand in front of the computer (yes, stand) and just start typing, but for the first time, I found nothing to type.

Was the first part really necessary? It does add something unique, but it lengthens the headline while not adding much. Also, who cares that it took me 15 minutes to get started writing an article?

2021 alternative: “How Overthinking Diminishes Authenticity in Your Writing”


11. “Life-Changing Lessons Learned From Charles Darwin, Thomas Edison, and Max McKeown”

This was a follow-up article based on the same premise: Take three people and find some good life lessons. I don’t remember how I decided on these three. I think I just started from good quotes.

Do you know Charles Darwin? Do you know Thomas Edison? Now, the real question: Do you know Max McKeown? That has to be one of the strangest mixes of people analyzed in a single article.

2021 alternative: “Life Lessons From a Motley Crew of Dudes From Different Periods”


12. “Helicopters + Vomit + Grand Canyon + Las Vegas + 50 Cent = Recipe for a Stress-Free and Unforgettable Wedding”

This is the story of my very unusual wedding. When I told people the story in person, they wanted to make a movie out of it, so I decided to write about it and publish it.

To me, that recipe sounds terribly stressful. I’m not sure why I used the phrase “stress-free”. The combination of words in the first part is very strange, but it actually does summarize my wedding day quite well. But looking at the headline, what’s in it for the reader? I guess a little bit of entertainment, but I don’t think anyone would ever use my recipe.

2021 alternative: “Lessons Learned From Puking Twice in My Wedding Helicopter”


13. “Become a Win-Master Using This Powerful Science-Based Method”

I think I came up with this overly intense headline when I started using CoSchedule’s headline analyzer tool. This scored freaking high! The article tanked. I never used the tool again.

Clickbait!

“Win-Master? Wtf is that?”
“Powerful? Says who?”
“Science-based? With your previous claims, sir, I don’t believe you anymore!”

2021 alternative: “Achieve Your Desired Results Using <insert method name here>”


14. “SKILL THE F UP!”

I think I was approaching my sixth month of having learned three new skills per month. I was seeing such good results that I felt compelled to just scream at my reader as a coach would.

“Thanks, I guess. Why are you screaming at me again?” says the reader.

2021 alternative: “Lifelong Benefits of Making Learning a Habit”


15. “Lessons Learned From a Grade School Notebook”

When I lived in Bangalore, I was looking for a notebook with three criteria in mind: It has to have a softcover, it can’t be ruled or gridded, and it has to be orange. That cuts the options down quite a bit. Thankfully, I found one, which turned out to be a grade school notebook. On the back of it was a powerful quote, which inspired me to write that article.

What adult learns from a notebook? And one aimed at children at that! It’s quirky, and I love it.

2021 alternative: “A Lesson Aimed at Children That Actually Had an Impact on My Adult Life”


16. “2018 Is the Year I Will Fail the Most”

My one-word theme for 2018 was “fail.” Near the end of 2017, I decided that in January 2018, I’d do the following, which really should have been impossible to do, yet somehow I achieved it:

  • Gain 15 lbs of muscles

  • Lose 3% body fat

  • Do three full-body workouts per week

  • Do 100 pushups, squats, and dips daily

  • Eat 5,000 calories a day

  • Write one article a day for 31 days in a row (I had never written publicly before)

  • Learn to meditate, and do it for 20 minutes daily

  • Learn to journal, and do it for 20 minutes daily

Those were insane goals. I really thought I’d fail. I planned to have crazy goals like that throughout the year (I did). For the most part, I didn’t fail. I learned a whole lot.

But let’s be honest, how strange is it to have “failure” as a New Year’s resolution? Strange headline. Strange resolution. But man, incredible results!

2021 alternative: “How to Set a New Year’s Resolution You Can’t Not Do”


17. “I Helped Someone, and I Liked It”

I think this came after I helped a homeless person and felt good about myself.

“Dude, is it the first time you helped someone in your life? Welcome to the club, but really, you should have joined it much earlier,” says anyone who has been helping others for much longer (aka, everyone).

2021 alternative: “Be Good for Goodness Sake and Nothing Else”


18. “Cheesy Alert: A Concrete Tip On How to Win At Everything You Do”

I don’t remember the exact context, but I guess it came after having a good streak of success on different things. Spoiler alert: That streak ended. I don’t win at everything I do. Not even close.

“Danny’s at it again with another clickbait title. At least, this time he’s warning us to not open it. Thanks, man!” said pretty much every reader, according to my stats.

2021 alternative: “Use <method name> to Achieve Your Desired Results”


19. “Pro Tips for Power Napping Like a King”

I wrote this based on my experience of going from not being able to nap to being consistently able to do it.

Was this written for the Middle Ages? Who aspires to do things as a king does these days?

2021 alternative: “Expert Tips on How to Effectively Power Nap in the Afternoon”


20. “That Dreadful Snooze Button and Fighting Dragons in a Sea of Flames”

I think I was drunk… Actually, it was a dry month. I guess after snoozing in the morning, I dreamt I was fighting dragons? Lesson: We’re all quirky, okay?

“Wtf? You high, bro?” says the reader who accidentally stumbled upon this deeply strange headline.

2021 alternative: “Don’t Snooze?”

Hope you enjoyed it and learned a thing or two!

— Danny