“I drew 16 portraits of my ex-girlfriends” sounds like the beginning of either a heartfelt indie film or a very specific court case.
Thankfully, it was neither. It started as a simple idea: I wanted to get better at portrait drawing, and I already had a mental library of faces
I could picture with surprising clarity. (Apparently my brain can’t remember where I put my charger, but it can remember an eyeliner wing from 2019.)

What I didn’t expect was how the project turned into a crash course in anatomy, memory, boundaries, and emotional “decluttering.”
Portraits demand attention. And attention, when you give it honestly, tends to teach you thingssometimes even the stuff you’ve been politely avoiding.

Why I Started (Besides the Obvious “Art Kid Energy”)

On paper, the goal was skill-based: improve facial proportions, train my eye for values, and stop making noses look like the letter “J.”
But there was a second motive hiding in the margins: I wanted a structured way to process old relationships without doom-scrolling my photo history.

There’s a reason creative practices are often used as coping tools. Drawing forces you to slow down and focus on the present task:
shape, shadow, gesture, expression. It’s hard to spiral when you’re busy trying to figure out why one cheekbone is doing parkour.

The Ground Rules (A.K.A. How Not To Be a Creep)

Let’s get this out of the way: drawing portraits of real people comes with ethical responsibilitiesespecially exes. So I set rules before I drew a single line.
If you’re considering a similar project, steal these rules like they’re a perfectly sharpened pencil.

• No full names, ever. In my sketchbook, each portrait had a number (1–16), not a label.
• No “gotcha” details. The goal wasn’t to roast anyone. This wasn’t a revenge montage.
• No posting without consent. Even if your art is “technically” yours, sharing someone’s recognizable likeness publicly can create real harm.
• No monetizing the project. If money enters the chat, privacy and publicity rights get complicated fast.
• Keep it respectful. If I couldn’t describe the portrait’s intention as “kind,” I didn’t draw it that day.

These boundaries didn’t ruin the project. They saved it. Instead of turning into a spectacle, it stayed what it was supposed to be:
a drawing challenge with a side of personal growth (served without the cringe garnish).

What Counts as a “Portrait” (And Why I Chose 16)

I defined a portrait as “a recognizable likeness, built with intentional choices.” That meant I wasn’t chasing photorealism.
I was aiming for the feeling of someone’s face: the tilt of a smile, the heaviness of an eyelid, the way eyebrows can say “I’m listening”
while the mouth says “I’m judging you a little.”

Why 16? Honestly, it’s a great number for momentum. It’s big enough to feel like a series, small enough not to feel like a life sentence.
Also, it gave me room to explore different media and styles without turning the project into a never-ending sequel.

My Portrait Process: From “Oval Blob” to “Oh… That’s Her”

1) Start With Big Shapes (Before Your Confidence Gets Fancy)

Every portrait began with a loose “envelope” shape: the outer boundary of the head and hair. Then I dropped a center line and a rough eye line.
If I skipped this step, the face would drift sideways like it was trying to exit the conversation.

I measured with my pencil at arm’s length and compared distances:
width of the head vs. height, eye spacing, nose-to-chin length. Nothing dramaticjust enough to keep reality on the mood board.

2) Landmarks Beat Details (Every Time)

Likeness comes from relationships between features, not from drawing a perfect eyelash.
I looked for anchors: the angle of the jaw, the width of the cheekbones, the distance from nose to upper lip, and the tilt of the eyes.
In other words: I was building a face like a map, not like a sticker collection.

I also learned that memory lies. Not maliciouslyjust casually, like a friend who insists they’re “five minutes away” while still in the shower.
So when I used reference photos (when I had them), I treated them like evidence, not vibes.

3) Values First, Pretty Second

Once the proportions were stable, I blocked in shadows in big, simple shapes. Not smudgy chaosclear value families:
light side, shadow side, and the in-between transitions. This was the stage where the portrait stopped looking like a cartoon and started looking like a person.

A weirdly effective trick: I squinted. It sounds silly, but squinting reduces detail and shows you the major value patterns.
If the face worked while squinting, it usually worked when I opened my eyes and faced the consequences.

4) Details Last (Because Details Are Liars)

I saved detailslashes, hair strands, sharp highlightsfor the final stretch. When I rushed them early, they became a distraction.
Like putting sprinkles on a cake that’s still batter. Delicious ambition. Terrible timing.

Medium Experiments: Pencil, Charcoal, and Digital

One reason the series stayed interesting was that I changed tools. Different materials forced me to see differently.
It also kept me from obsessing over “one perfect style,” which is artist code for “hello, creative paralysis.”

• Graphite pencil: Great for controlled shading and subtle transitions. Also great for overthinking.
• Charcoal: Bold, fast, and dramatic. It taught me to commit to dark values without fear.
• Ink: No erasing. Every mark is a decision. This medium exposed my habits immediately.
• Digital (tablet): Convenient, flexible, and dangerously easy to “fix” forever. I learned to set time limits.

Switching media also changed the emotional tone. Charcoal portraits felt like memoriessoft edges, big shapes, moody contrast.
Ink portraits felt like conclusions. Digital portraits felt like alternate timelines where I actually know how layers work.

What the Portraits Taught Me About Breakups (Without Turning Into a Motivational Poster)

Here’s the surprise: drawing exes didn’t make me nostalgic in the way I expected. It made me specific.
Instead of “everything was good” or “everything was terrible,” I saw nuance: kindness mixed with incompatibility, fun mixed with friction.

The project also highlighted patternsmine. Not in a self-blaming way, but in a “wow, I really do have a type” way.
For example, I noticed I often remembered expressions more than outfits. That told me something about what I valued: how someone looked at the world,
not what they wore in it.

And because I wasn’t texting anyone or reopening conversations, the reflection stayed internal. Quiet. Honest.
It felt closer to journaling than to “reliving,” which is an important difference if you’re trying to move forward.

If You Want to Try This Project, Here’s a Healthier Version

You don’t need 16 exes (or any exes) to benefit from portrait studies. You just need a structured series and a respectful approach.
Here are three options that keep the growth and reduce the drama.

Option A: The “Memory Portrait” Challenge

1. Choose 10–20 people you’ve known (friends, family, teachers, fictional charactersanyone).
2. Draw from memory first for 10 minutes.
3. Then compare to a reference (if you have one) and redraw with corrections.
4. Write one sentence about what changed and why.

Option B: The “Consent-First” Portrait Series

1. Ask 5–10 people if you can draw them.
2. Tell them if you plan to post it. If they say no, it stays private. No negotiation.
3. Focus on likeness and mood, not perfection.

Option C: The “Emotional Closure” Sketchbook

Instead of drawing specific people, draw symbols: places you went, objects that mattered, colors that feel like that season of your life.
You still process the story, but you don’t put anyone’s face on the internet.

Common Portrait Problems (And the Fixes That Actually Work)

“It looks like them… but also like my cousin?”

Check feature relationships: eye spacing, nose length, mouth width, and the angle of the jaw. Likeness lives in proportion, not detail.

“The eyes are dead.”

Add structure: eyelids have thickness, the iris sits under the lid, and highlights should be placed with intentionnot randomly like glitter fallout.

“The shading is muddy.”

Simplify values into groups. Keep lights clean, shadows clean, and transitions controlled. Smudge less. Decide more.

“I hate it halfway through and want to quit.”

Congratulations, you have reached the Mid-Drawing Panic Zone. Set a timer for 15 minutes and only fix proportions.
Not details. Not hair. Proportions. Most portraits recover once the foundation is corrected.

Conclusion: Art Can Be Closure, If You Add Boundaries

Drawing 16 portraits of my ex-girlfriends didn’t “solve” my past. It organized it. It turned blurry emotional noise into something I could look at,
learn from, and then close the sketchbook onwithout slamming it dramatically like a TV character.

If you take anything from this, let it be this: you can make art from your life without turning people into content.
Respect matters. Consent matters. And if your creative project helps you grow while staying kind? That’s not just good art.
That’s good character.

Extra: From the Sketchbook (Experiences After Portrait #16)

By the time I reached portrait sixteen, I had learned the technical stuff the hard way: faces aren’t “features,” they’re structures.
A nose isn’t a symbol; it’s a form with planes. A mouth isn’t a sticker; it wraps around the cylinder of the muzzle.
But the bigger lessons weren’t about anatomy. They were about attention.

The first few portraits felt loud. My brain tried to narrate everything: the beginning, the ending, the what-ifs.
It wanted to turn the drawing into a documentary. So I gave myself a rule: while I draw, I only think in artist language.
Not “she said this,” but “the shadow under the cheekbone is triangular.” Not “that night was awkward,” but “the brow ridge is stronger than I remembered.”
Weirdly, that helped. It separated the person from the story and let me focus on the human reality in front of me: a face, an expression, a moment.

Somewhere around portrait seven, I noticed something almost embarrassing: I was kinder on paper than I had been in my head.
When you draw someone, you have to look for what makes them uniquely themwhat’s beautiful, what’s distinctive, what’s alive.
Even if the relationship ended poorly, the act of drawing forced me to acknowledge their humanity without reopening the relationship.
It wasn’t forgiveness in a dramatic movie-scene way. It was more like emotional maturity showing up quietly and doing the dishes.

Portrait ten was the hardest, not because I couldn’t draw it, but because I could. The likeness arrived fast.
That’s when I realized how powerful memory can beand how careful you have to be with it. When a face comes easily to you, it doesn’t always mean you’re meant
to go back. Sometimes it just means your brain is good at patterns. I finished the portrait, wrote one line in the margin (“Good times were real; so were the reasons it ended”),
and moved on. The moving on part was the victory.

I also learned how important privacy is for creative work. If I had tried to perform this project publiclyposting every portrait, inviting comments,
turning it into a spectacleit would’ve changed the intention. The drawings would’ve become arguments. Or trophies. Or bait.
Keeping the project mostly private protected the people involved and protected me from turning my growth into a popularity contest.

And finally: portrait sixteen taught me the difference between closure and erasure. Closure isn’t pretending something never mattered.
Closure is being able to say, “That mattered, it shaped me, I learned from it,” without needing to relive it.
The sketchbook became proof that I can hold complexity without drowning in it. Also, proof that I should probably practice ears more.
Seriously. Ears are tiny chaos machines.

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