A Ruthless Gangster’s Greatest Fear: The Forbidden Fruit More Lethal Than Heroin

by Michael de la Guerra in Essays

You, me, and your crush walk into a bar. I leave. What happens? This isn’t a joke. It’s a nightmare.

At least it would be for me, depending on the crush, and the stage of my life.

Crushes can be embarrassingly debilitating.

One of the most gangster friends I’ve ever had in my life was this guy I met in rehab, Sean. He was a heroin addict, and he’d definitely done some pretty heinous crimes, like kidnapping for ransom, strongarm robbery, and probably murder.

And he was hilarious; he was bald, and wore baggy clothes with chunky rectangular sunglasses, even at night.

The way he bonded with people was by making fun of them. He’d do it in a way that was so funny, you ended up laughing at yourself with him.

But he turned into a complete wimp when his crush was at the same event as us, or in the same room.

Alexandria: the girl from east side Pico Rivera (an apparently forbidden fruit based on where he was from, and I never was able to understand all the street politics he tried to teach me).

We talked about it one night. He was embarrassed that someone affected him like that. It made him feel weak. Like “a little bitch.”

It’s normal, I told him. It means you’re human. Sean spent so much time on the street putting up the rock-hard front, that the slightest vulnerability like a simple crush pushed him over the edge.

Most of the time the discomfort we feel when we have a big crush is due to a lack of control. We’re reminded how easily our emotions can get the best of us.

I’ve done a lot of work in the self-esteem department over the years. I was shy and chubby not too long ago, but now I’m fit and slightly above average on the confidence scale. It’s been great, but a couple of weeks ago I ran into a girl I’ve had a crush on for ten years at a baby shower. It completely paralyzed me. Everything I worked for came crashing down.

After some digging (I mean, this slight interaction ruined me for the rest of the day — I could not stop thinking about how I acted), I uncovered the truth: she triggered the part of me that felt I was undeserving of her in the first place. She brought up the old, self-conscious part of me who didn’t even see her as a person, just a mirror for my own insecurities.

I wish I could’ve told Sean.

He would have laughed at how when she was passing out the cake, she came up to me and said, “Are you gonna be okay if I hand you a piece?”

Unfortunately, Sean is back on the streets.

He’s been strung out again for years now. If he convinced himself he was weak because of a schoolboy crush, I can only imagine what other, more powerful emotions could do to him.

I hope one day Sean gets to experience letting his walls down and being vulnerable with someone who loves him.

And every time I let my mind convince me that I’m weak for feeling natural human emotion, I’ll think of him, and remind myself how lucky I am to feel this way.

Exploring the Poetic Voice: Michael de la Guerra's Literary Landscape

Michael de la Guerra's online portfolio presents a rich tapestry of poetry, essays, and artistic reflections that examine the complexities of modern relationships, cultural influences on romantic expression, and the psychological dimensions of love and loss.

A Distinctive Voice in Contemporary Poetry

Throughout his work, de la Guerra demonstrates a remarkable ability to blend raw emotional honesty with technical craft. His poetry collection features pieces like "HAPPY IN BED," which tackles modern dating concepts like "situationships" with a blend of dark humor and quiet dignity. The poet often acknowledges his own vulnerability while maintaining a self-aware perspective about the human condition.

His "Medical School Romance Poem" captures fleeting connections with strangers in institutional settings, pondering whether brief shared moments might someday become meaningful memories for the other person. This theme of ephemeral connections appears frequently in his work.

Cultural Exploration and Scholarly Depth

De la Guerra's scholarly side emerges in comprehensive explorations like "Romantic Poetry: Poems About Love Across Cultures," where he examines how different cultural traditions approach romantic expression. From Tang Dynasty China to Pre-Columbian Mesoamerica, he traces the universal human need to capture love's complexities through poetry while highlighting how each society filters these emotions through unique cultural lenses.

His work often begins with personal anecdotes - like his inability to communicate directly with his Spanish-speaking grandmother - before expanding into broader cultural analysis. This technique creates an accessible entry point for readers into complex literary traditions.

Dark Poetry and Psychological Insight

The "Dark Love Poetry" guide demonstrates de la Guerra's understanding of how poetry serves as both artistic expression and psychological processing. He distinguishes between performative darkness and authentic shadow work, offering readers insight into how true dark poetry transforms private pain into shared understanding.

Throughout this exploration, he connects psychological concepts like attachment theory to poetic expression, showing how disorganized attachment might manifest in certain poetic tendencies, while earned security allows for different forms of creative expression.

Personal Narratives with Universal Appeal

In shorter reflective pieces like "A Ruthless Gangster's Greatest Fear," de la Guerra reveals his ability to find profound meaning in unexpected places. By juxtaposing the vulnerability of a hardened criminal experiencing a crush with his own similar feelings, he creates a meditation on how emotional authenticity connects us across seemingly vast differences.

This approach - finding universal human experiences in specific, often overlooked moments - characterizes much of his work, making even his most personal reflections resonate with readers from diverse backgrounds.

A Multi-Faceted Creative Practice

Beyond his writing, de la Guerra offers resources for fellow poets and writers, including prompt generators and workbooks. His website showcases his parallel visual art practice, including abstract, Japandi, and dark abstract wall art collections.

This integration of visual and literary arts reflects a holistic creative approach, where different expressive forms complement and enhance each other rather than existing in isolation.

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