The Flake Files: Chapter I

An unexpected message awaited in my [popular online dating site] inbox.



New message from [name redacted]
January 4, 2019 at 7:26 PM

 “I’m free this weekend. What are your plans? [phone number redacted]”

It caught me off guard because I never expected to hear back from her. In our initial correspondence she expressed, unprompted, an eagerness to go on a date (I saw you like sushi, it’s my favorite too. Let me know if you ever want to grab a drink sometime.”).

Excellent. After ogling the profile pic of her in a tight low-cut top—turns out I did want to meet for adult beverages (imagine that?).

I asked, on a Tuesday morning, when she was free.
When a few days passed without a reply—I assumed she, despite the date being her idea, had a change of heart (her loss, I thought). So imagine my surprise to see that, although her response came late on a Friday evening (more than 3.5 days after my message), she was still interested in getting a drink that weekend.

I called the next morning. Left a voicemail.
Didn’t hear from her that weekend.
Never heard from her.


In a rational world—under normal circumstances—this would’ve been a stupefying set of circumstances.

An independent observer would most likely be flummoxed by this outcome.
Does it not defy logic that someone would exert so much effort (suggest a date, offer their personal information)—only to flake?


Unfortunately, this result has become all too common.
After a lengthy hiatus, I’ve returned to a dating landscape in which this isn’t an abnormal occurrence.

Consequently, I wasn’t the least bit surprised; it’s happened before.


Months ago, after a lengthy back and forth on [popular dating app], a young lady suggested we transition our correspondence off the Internet.

“So shall we graduate to the phone yet?
[number redacted]
Texting can be convenient at times but talking is important” 

I called the following day. Left a voicemail. Never heard from her.


Not long ago, I engaged another woman in conversation on [popular dating site]. She divulged her number promptly during the initial correspondence.

 “Of course! Feel free to give me a call at [number redacted]
We can talk about all the very bad food I can cook for you to sabotage your diet :)”

Oooh! No one’s cooked for me since [ex-girlfriend].
I envisioned the glory of lying on the couch as she prepared devastating calorie-laden meals while wearing that bandage dress (which accentuated them curves right) and the heels she rocked in her profile pic.

Yes, please.

I called a few hours later, which seemingly caught her at an inopportune moment.

“Let me call you back in 15 minutes.”

 15 minutes came and went. Never heard from her. Ever.


Dating is a maddening endeavor.
Thus when my comrades complain about their wives/girlfriends and proclaim to envy my bachelor lifestyle, I quickly remind them that the grass ain’t always greener.

Which the aforementioned incidents illustrate in exquisite detail.

Hold your partners tight, nonbachelors. It’s rough out here.


Bachelorhood: A Brief Essay

There was a time—not long ago—when it appeared my legendary bachelor days were a thing of the past.


Deleting my online dating profiles—as I did while lying in bed one night—was the definitive conclusion of a lengthy chapter.

This is it, I thought.

No more serial dating. No more outlandish tales.
No more commitment-phobia (if, after decades of resistance, even bachelor icon George Clooney renounced the single life—who was I to buck the trend?).

The uncertainty of single life would soon be supplanted by the stability of commitment.

I had an exceptional run, but the time for embracing a lifelong allegiance—with my girlfriend of more than a year—had finally come.

Rings were carefully appraised.
Two separate residences were condensed into one.
Half my closet space now overflowed with skirts, blouses, and heels.
The bachelory “artwork” (ie, the UFC 189 framed poster)? Jettisoned for more mature paintings.
She provided Netflix and Hulu; I shared Amazon Prime and HBO Now.
We weren’t quite ready for babies. We went half on a badass dishwasher instead.

The foundation was set for a life lived happily ever after. Together.


Fast forward one year: I’m now, inexplicably, as single as any man has ever been.

In the aftermath, the specifics needn’t be rehashed.
It only matters that I am, against all odds, once again a bachelor.

Yeah, so—about those online dating profiles I deleted.

And so it begins. Again.

I Got Trolled on National Television

My heart was about to pound through my chest cavity.


Now, I’m not unfamiliar with terror-inducing situations.
Critical job interviews.
High-stakes football games.
Experiencing EXTREME paranoia after devouring a weed-laced brownie.
Having a gun pointed at my face.

However, I can’t remember being more distressed than at that moment.

It was a tense situation.
I sat alone at the restaurant table, wearing a microphone. And makeup. Surrounded by cameras. And TV producers.

I anxiously fidgeted with my drink in anticipation of my blind date making her grand appearance. And, moments later, what a spectacular entrance she made. After much anticipation—the spectacle had begun.


This’ll sound ridiculous coming from someone who publicly details my most embarrassing moments in painstaking detail: I’m a private person.

Thus, when I received an email, via my online dating profile, about possibly being on TV—I was, understandably, reluctant.

Although I mask it with ridiculous bravado, I’m a man of immense insecurities. The idea of being broadcast to millions of people—including family, friends, and colleagues—is horrifying.

Make no mistake: I’d rather have Walking Dead zombies chew the flesh from my face than be humiliated on national TV.

I’d prefer Negan bash me over the head with Lucille—his barbed wire–laced bat—than face such shame.

So why entertain such a proposal?
The producer executed a masterful sales pitch. Instead of a blind date—it was more of an opportunity to help an attractive, outgoing woman learn why she wasn’t having more dating success. My role: string together a few coherent sentences, then enjoy dinner and adult beverages—compliments of the show. Worst case: I’d emerge with an entertaining tale.

After much deliberation—and an impromptu Skype audition—I agreed to participate.

What’s the worst that could happen?


Famous last words.


Something wasn’t quite right.


My date entered the restaurant—rocking a long, tight dress and the highest of heels—like a model gliding down the runway.

I stood, told her she looked great, and helped her get seated. However, because it was being filmed for a talk show—the producer made us repeat “the scene” at least 4 times.

Once we finally got situated, it wasn’t long before I could tune out the surrounding distractions and focus on my date. She was as advertised: attractive, strong personality.

The first few minutes went well.

Unfortunately, the good times were short-lived—shit spiraled WILDLY out of control shortly thereafter.

I’m unsure at which point I realized something was amiss.

Maybe it was when she shooed our waiter away like an annoying gnat.
Or when she continuously called Tito’s vodka—Titty’s vodka.
Or when she mentioned her mixed-breed purse poodle: Michael Jackson.
Or when she demanded we Skype AT LEAST 5 times a day.
Perhaps when she repeatedly interrupted me to steer the conversation back to HER.
Maybe when she harangued me about—everything.

But after being relentlessly badgered about why I don’t worship Beyoncé, a pop singer whose music is targeted solely to those without a penis—I could no longer ignore the devastating truth: I was being trolled by The [name redacted for legal purposes] Show.

The final straw was when she berated me for thinking Queen Bey had 2 kids, not 1 (sorry, Blue Ivy).

I staggered from the restaurant a defeated man—convinced that my blind date was playing a ridiculous, over-the-top caricature of every man’s worst nightmare for the cameras. Because no one could be that off-putting, okay?

Completely humiliated, I told NO ONE about the debacle. Hopefully, by some inexplicable act of mystery, the episode wouldn’t air—and I wouldn’t have to embrace the devastating shame I so desperately wanted to avoid.

In the aftermath, I attempted to expunge the fiasco from my memory—much like a PTSD-stricken soldier trying to forget the horrors of combat. After several months passed without hearing anything, I believed I’d miraculously dodged a bullet.

Until, one unfortunate afternoon, I got a text from a family member: “Are you going to be on The [name redacted for legal purposes] Show tomorrow?”


The Night He Desecrated the Bro Code

Few events can rival the unbridled glory of fight night.


Some of my most memorable Saturday evenings have been spent at a raucous sports bar bearing witness to a highly anticipated UFC pay-per-view.

These events successfully integrate my favorite pastimes:

Hanging with the homies? Check.
Trolling said homies with the most childish insults imaginable? Of course!
Watching the most thrilling sport known to man? Check!
Guzzling an incomprehensible amount of adult beverages? CHECK!
Shoveling into my face the most grease-soaked, calorie-laden, artery-clogging, life-shortening bar food I can order? Goddamn right!

Saturday, April 23, 2016 promised to be yet another legendary night—we gathered to behold the spectacle of UFC 197: Jones vs St Preux.

Om,* a longtime fight night participant, (*not his real name) introduced a wildcard by bringing a potential lady friend.

Now, it wasn’t the first time a girl’s joined our UFC festivities; the ladies are always welcomed. Whenever a new woman is present, however, we attempt to be on our best behavior.

(And by best behavior, I mean:
–No juvenile penis jokes a sixth-grader would make
–Refrain from insulting any of the fellas by insinuating they secretly have female genitalia)

The ladies have enjoyed the fellowship of fight night for years without incident.

Until now.

After swooning over video of badass UFC strawweight Claudia Gadelha facing off against a rival, I commented: “She’s adorable.”

Om, sitting across the table from us, leaned toward the girl and whispered: “Who uses the word adorable?” (Fun fact: I have, in fact, heard HIM use that word.)

And just like that, dude had blatantly violated the sacred Bro Code.

Ahh, yes—the Bro Code. It’s been called several different names throughout time (Man Laws, Guy Code, The Man Commandments, etc). Think of it as a universal set of rules by which all men should abide. The common theme: Don’t be a douche. To anyone. ESPECIALLY your friends.

Though it was a relatively minor infraction, he was guilty of disobeying a basic tenet:

This should require no explanation.
Few things are more reprehensible than disparaging your brothers in seeking a woman’s approval.

Unfortunately, it wouldn’t be Om’s only transgression on this night.

His next offense, however, would be infinitely more egregious.


Some background: Om and I have frequently discussed, in great detail, how our nonreligious beliefs make dating more difficult. It’s a complex, nuanced discussion. I’m an agnostic. And though he’s STILL on the fence about the existence of a higher power, we agree on one thing: when devout women learn a man is nonreligious—they immediately think less of him.

Which made what transpired next all the more disgraceful.

I was so engrossed in the Yair Rodriguez/Andre Fili brawl that I almost didn’t hear Om, once again, lean toward her and inexplicably whisper: “Von doesn’t believe in God.”


Now, that statement could’ve been acceptable in the throes of philosophical discourse.
Or if broached during a spirited religious debate.

But whispering it to her—and not addressing the group?
In a sports bar?
Amidst the mayhem of fight night?

Never has the Bro Code been so thoroughly desecrated.

Instead of immediately calling him on it (and thus likely ruining his chance with the young lady)—I waited a few days.

When asked to explain himself, Om could only muster a weak, implausible defense: he thought it was an interesting fact, about me, that she needed to discover—at that exact moment.

Additionally, in the face of such scrutiny—he was completely unapologetic.
He felt ZERO remorse for his treacherous betrayal.

The mild anger I briefly experienced quickly dissipated.
It became disappointment. Pity.


May the day never emerge when I—nor any other decent gentleman—need to resort to such deplorable tactics to capture a woman’s affection.

Flashback: The Night SHE Paid First

The male ego can be incredibly fragile.

Consequently, when my lady friend retrieved her wallet and attempted an unprecedented act—paying for a first-date dinner—I didn’t take it as an authentic gesture of goodwill.

I interpreted it as an emasculation.

First dates for me typically involve drinks at a nice bar or restaurant. Without fail, an unspoken test commences at evening’s end once the black leather envelope is left at the table. The most frequent outcomes:

  1. She graciously allows you to foot the bill
  2. She makes a halfhearted fake attempt to split the check—while fully expecting you to overrule her and pay

I’ve witnessed the latter scenario countless times. Enough to determine that something was amiss with my lady friend. She wasn’t bluffing.

My testosterone-fueled reaction was to intervene.
I couldn’t let this woman—whom, until that night, I’d only corresponded with via the Internet—pay for my drinks and sizzling steak platter.

What respectable gentleman would allow that to happen?

Those thoughts soon gave way to a stark realization: Why not let her pay?


My hesitance undoubtedly stemmed from archaic gender roles.

Many a decent yet ill-informed brother has been mocked relentlessly by bloodthirsty women—during spa treatments, in hair salons, and at other estrogen-fueled communions—for not knowing his role.

Let’s be clear, gentlemen: women expect YOU to pay.
It’s a universal truism that’s prevailed since the dawn of time. Our hunter-gatherer ancestors—who wore outlandish loin cloths and routinely risked their lives to provide food for women—have been replaced by gentlemen in blazers who need only produce a credit card to feed a lady.

In contemporary times, however, a gender revolution has arisen where independent women refuse to be viewed as unequal to their Y-chromosomed counterparts.

But even the most staunch gender equality advocates will concede that feminism flies out the window when:

  1. The garbage needs to be taken out
  2. A frightening bump in the night needs inspection
  3. After a long day in heels—she needs a seat on the train
  4. Snow needs shoveling
  5. The first-date check arrives

In the history of Western civilization, no woman’s ever debriefed her girls after a first date and said: “After we went halfsies on the 2-for-1 shrimp extravaganza at Red LobsterI couldn’t wait to take him home and have my way with him.

Then there’s the financial hierarchy paradox:
Oh, she makes more than you? By a staggering amount?
Doesn’t matter, comrade.

Case in point: only the most confident of man can pursue a woman who outearns him. As someone who’s repeatedly dated women in a much higher tax bracket—I have firsthand experience on the matter.

However, make no mistake—I STILL paid on the first date. ALL of ’em.


Until one fateful evening.

The monumental significance of my lady friend’s act cannot be overstated.
She effectively took a centuries-old, time-honored tradition—and punched it in the goddamn face.

I observed in stunned silence as she confidently unleashed her black credit card, slid it into the envelope, calmly dismissed my objections, and nonchalantly continued our conversation—as if she didn’t just execute the most spectacular mind-fuck in dating history.


If her actions were indeed an advanced psychological tactic, it was devastatingly effective.
Afterward, our date continued at a South Loop lounge.
Because of my wounded pride, I couldn’t allow her to again foot the bill for our adult beverages.

Know what else I paid for?

EVERYTHING else for the duration of our courtship.

Although our romance was short lived—shit went downhill after her attempt to baptize me—I learned an invaluable lesson that night.

In theory, the woman paying first sounds like a revolutionary idea with potential to forever alter the dating landscape.

In reality, however, I doubt it’s a shift the male ego is prepared to embrace.

Flashback: She’s Sensitive About Her Panties

To say my lady friend wasn’t the least bit amused by my juvenile hijinks is a massive understatement.


Thus, she wasted no time dismissing me—permanently.

Her response, via inbox: “Obviously some one let you out of your play penI am not going to view your link and honestly not interested in conversing with youSo you know the restPeace


Consequently, my time seeing the girl who inspired the Rodman Dating Theory had come to a screeching halt.

In the aftermath, her retort begs an obvious question: what could I have possibly done to provoke such a fierce backlash?


It’s not often that a devastatingly attractive woman makes a move on me.

So, it took a moment to wrap my brain around what was happening.

I logged on to MySpace one fateful day in 2007 to find an inbox from a mysterious young lady. Describing her as a bombshell of the highest magnitude isn’t the slightest exaggeration. Apparently she was new to the area and looking to connect. With ME.

Needless to say, I wasted little time seizing the moment.

Now, those expecting a we-lived-happily-ever-after tale will be sorely disappointed. Instead, we went out a few times before I discovered the shocking truth: she was, quite possibly, the flakiest chick in North America.

I ignored my zero-tolerance policy the first time she flaked.
After the second fiasco, however—enough was enough, goddammit.
I vowed to NEVER entertain her antics again.

But of course, because of her staggering hotness, I relented a month later when she suggested we hang out (thus spawned the Rodman Dating Theory).


For obvious reasons, I called to confirm that she was still coming over the next day for my extravagant home-cooked meal (and by extravagant, I mean the most basic of spaghetti recipes).

She recapped, during our conversation, the details of her day:
Her quest to find a digital camera.
The delectable seafood she bought.
The incompetent drivers on the road.
Buying underwear at Target.
About how—wait, what?!

*record scratches*

She buys panties—at Target?!

Now, let’s be clear: it’s completely irrelevant where a lady purchases her knickers. Throughout time, no woman’s ever been jettisoned from bed because her undies lacked a Fredrick’s of Hollywood tag.

Lace is lace. Cotton’s cotton.
Despite what many erection-inducing undergarment ads tell us—women needn’t get all their unmentionables from seductive lingerie outlets (although it wouldn’t hurt).

That being said, this was my chance to tease her. Playfully.

When dealing with a stunning lady—who’s likely bombarded with compliments by every douche she meets—it’s critical to occasionally dole out a nice ribbing to keep her somewhat grounded.

I took full advantage: “Oh, you get your underwear from…Target? Interesting.

She laughed and said she also frequents Victoria’s Secret—but the Target ones look just as good as those.

And if I saw her in those particular red lace ones—I’d never know the difference.

Most gentlemen would’ve seen that last statement as an opportunity to transition to racier banter (“Oh, I’m supposed to take your word? Prove it.“). Obviously, I would’ve liked nothing more than to bear witness to her in underclad glory. I do, after all, have a penis.

For some inexplicable reason, however, I chose to unleash another lame Target joke.

We both laughed. If she was irritated by my sophomoric antics—she hid it well. Although she did call me an asshole before we ended the call.

The next day she canceled our date (of course she did), citing the snowstorm that blanketed the area.

Unfazed, I replied: “Its cool. We can do it some other time. Have fun in your Target underwear.”

LOL,” was her reply.


Unwilling to let a good thing die—the next morning I took the joke even further.

It didn’t take long scouring the Target website before I discovered their most hideous panties: Depends adult diapers.

I cackled maniacally before sending her the link in a MySpace inbox with the subject line: I found your Target underwear online.

I checked my inbox a few hours later—thinking it’d give her a good laugh.

I’ve never been so spectacularly wrong.

High Times in Jamaica

She had to be possessed by a supernatural entity.


There’s no alternate explanation.
Her body convulsed violently; she began chanting. Demonically. If I hadn’t witnessed it, I’d never believe a human capable of producing such a terror-inducing sound.

It was a horrifying ordeal. Several tension-filled moments elapsed before we successfully thwarted her frenzied outburst; afterward, she collapsed into a catatonic sleep on a beach chair.

In the aftermath, a local asked what could’ve caused such an outburst.
Sadly, I knew all too well what was responsible: a brownie—one laced with potent local ganja.

I’d subsequently learn that the amount she had—one ENTIRE brownie—should last a few days. She devoured hers in minutes.

Unfortunately, so did I.
Thus, I had to embrace a horrific conclusion: it was only a matter of time before my epic meltdown commenced.


It seemed like a good idea at the time.

Vacation is, if nothing else, an opportunity to partake in new experiences.
Thus, when our cabbie asked if I’d like some weed brownies—how could I refuse?

I’d never experienced the sensation of getting high; brownies provide an opportunity to do so without the annoyance of marijuana smoke. Additionally, where better to get lifted than Jamaica—a place known for its ganja?

Yeah, go ahead and sign me up for that, comrade.

After taking us to the famous Seven-Mile Beach, the cabbie—true to his word—returned 30 minutes later with our stash.

I couldn’t get my hands on the product fast enough.

Now, if brownies came with directions—they’d have warned us to take it easy. Absent any guidance, however, we tore into our baked goods with reckless abandon.

Unsurprisingly, everything spiraled out of control from there.

MISTAKE 1: Believing the effects of edible weed are instantaneous.
MISTAKE 2: Thinking that not feeling an immediate high was a license to eat even MORE.

The consensus was that our brownies were ineffective. The narcotic equivalent of snake oil. No one felt a damn thing. Damn shame, I thought.

Afterward, as I played frisbee in the ocean—a chilling, blood-curdling sound stopped me dead in my tracks. 


I stood over my fallen comrade wondering if the same fate awaited me.

Although she fell first—she definitely wouldn’t be the last brownie-related casualty that afternoon. The ganja had now begun to derail those who dared mock its potency. Folks were dropping like flies.

It’s as if we were in a (Jamaican) zombie movie.
Instead of being infected by the undead—we fell victim to incredibly potent marijuana. Capable adults slowly devolved into zombified, non-functional ghouls. It began with giggling. Then slurred, incoherent speech—followed by dizziness. Ultimately, my stoned comrades fell into a deep sleep—sometimes interrupted by projectile vomiting.


Though my travel mates had fallen—I was determined to remain the last man standing. This shouldn’t, however, suggest that I felt no ill effects.

I was lethargic. Dizzy. Yet my heart seemed to race at 1000 BPMs.
My thought rate also increased; I carefully analyzed every minor occurrence.
I was tweaking, as the kids say; making it to the bathroom without faceplanting was a major feat. I barely kept it together.

Worst of all—extreme paranoia set in.
Throughout the ordeal, a security guard for the beachfront bar attended to us. The dude—a linebacker of a man—was instrumental in our care.

Yet I somehow, in my inebriated state, convinced myself that he was out to A) steal all of our valuables, and B) throw me in jail for buying illegal narcotics. Yikes!

Although, in my cannabis-fueled spiral, everyone’s voice sounded like Charlie Brown’s teacher’s (Womp-wah-womp-wah-wah)—I could’ve sworn he was telling me that he was gonna lock me up. Then throw away the key.

Fuck! I didn’t wanna rot in a Jamaican cell for the remainder of eternity.

The weed had successfully transformed me from epic badass—to a sniveling coward.
In that moment, I was no longer worthy of the privilege of wielding my penis.
If someone came along and revoked it—I couldn’t protest.

My fear and paranoia peaked when the security guard insisted I eat some mysterious grub, then wash it down with a strange liquid. Turns out that he wasn’t putting something in my system to frame me—it was a potent elixir: a clove of garlic and coconut water.

Vomiting ensued.
And that was it—I miraculously recovered.
My brownie-induced nightmare had finally come to an end.

It’d take some time before my comrades would come around—but eventually everyone made a full recovery.

Retrospectively, we can all make light of our high times in Jamaica now.
In the moment, however, it was no laughing matter.


If I never cross paths with another weed brownie—it’ll be too soon.