Bayverse!Leo as a Boyfriend – Headcanons
(Because even if I don’t like him, he deserves better characterization and development. And besides, I love overanalyzing.)
Pairing: Leonardo x Female!Reader
Warnings: Overprotectiveness, possessive behavior, affection-starved. Subtle (but present) hints of: narcissism, egocentrism, perfectionism, spirituality, insomnia. I developed him so well that I actually like him now—I don’t like that.
Leonardo, as a partner, would be a fascinating study in contradictions. At first glance, he seems like the perfect boyfriend—disciplined, loyal, protective, someone you can trust without hesitation. But being with him isn’t easy.
Not because he’s cold or indifferent—on the contrary, he feels too much. He’s just spent his entire life learning how to hide it. To him, emotions are a double-edged sword: love can give you strength, yes, but it can also make you drop your guard, make mistakes, and risk everything you’ve fought for.
And Leonardo can’t afford that luxury.
Since he was young, his identity has been tied to duty. He’s not just an older brother—he is the older brother. The leader. The one who must always have the answers. There is no room for error, no space for doubt. That’s why, if he ever fell in love, he would do so with the same intensity he applies to any challenge—with absolute commitment. But also, with a need for control that can be suffocating.
It’s not that he doesn’t trust his partner. It’s that he needs to make sure nothing puts her in danger. That she’s safe, that there are no loose ends, that every move is calculated. Don’t expect Leo to be the laid-back boyfriend who goes with the flow. He will want to protect you—even from things that might not even be a real threat.
If he comes to your house and you don’t answer, his mind will assume the worst before even considering that you were simply in the shower. If you go out alone at night, he won’t be at ease until he knows you made it home safely. Not out of jealousy, but because the thought of losing someone he loves terrifies him. But instead of expressing that fear, he translates it into rules, into planning, into strategies.
Because Leonardo doesn’t know how to handle what is beyond his control.
This was evident in Out of the Shadows. His instinct was to make decisions for everyone, to divide the team when he felt they were weakening. He truly believed he was doing the right thing, that carrying the burden alone was the best course of action. But in the process, he lost sight of what his brothers really needed. And that’s exactly how he would be in a relationship—not out of malice, but because he believes being the strong one is his duty.
And while Leo loves with every fiber of his being, he doesn’t say it easily. He’s not the type to look you in the eyes and just blurt out an “I love you.” His way of showing affection is more silent, more tangible. He will remember exactly how you like your tea, he will learn to pick up on even the slightest change in your tone of voice, he will make sure you always have an escape plan in case things go wrong. But if you expect spontaneous hugs or verbal expressions of love, you might find yourself frustrated. Not because he doesn’t feel it, but because, to him, love isn’t something you say—it’s something you prove.
However, if someone manages to break through his armor, they will see something that few have ever witnessed. Because beneath all the rigidity, the discipline, and the self-imposed perfection, there is a boy who never had the chance to make mistakes. A boy who has spent years carrying a tremendous weight, who can’t remember the last time someone saw him and not just the leader. A boy who desperately needs a space where he can stop being the strategist, the protector, the flawless Leonardo… and simply be Leo.
Leonardo isn’t someone who easily succumbs to distractions. Not because he doesn’t enjoy them, but because he’s always believed his time should be invested in something useful. Yet on the rare occasions when he allows himself to let his guard down—in the privacy of his room or on a quiet night at the lair—small details reveal who he truly is beyond being the leader of the Teenage Mutant Ninja Turtles.
For instance, he enjoys science fiction movies and TV shows. He wouldn’t admit it out loud—after all, Mikey would never let him forget it—but there’s something about exploring space, about advanced civilizations and the ethical dilemmas these worlds present, that fascinates him. Perhaps it’s because he sees his own struggle reflected in them: leaders forced to make impossible decisions, burdened with responsibility, torn between duty and heart. Whether it’s Star Trek, The Expanse, or even some of the more philosophical tales of Ghost in the Shell… Leo sits with his arms crossed, pretending not to be too interested, yet if someone pays close attention, they’ll notice the intensity in his gaze and the way his fingers tense with every twist in the story.
And although everyone sees him as the serious one, it’s not that he lacks a sense of humor. His humor is just more subtle, drier, more ironic. He won’t burst out laughing like Mikey or be as explosive as Raph, but if you’re close enough, if you’ve earned his trust, you’ll notice that there are moments when he quietly drops a joke in a neutral tone, waiting to see if you catch it. And when you do, when you respond with a retort just as sharp, the corner of his mouth barely curves, as if he’s quietly satisfied with the interaction.
But if there’s one thing that truly brings him peace, it’s tending to his bonsai trees. It’s a hobby that no one in the lair seems to fully understand. Mikey calls them boring, Raph jokes that they’re just “miniature trees,” and Donnie respects the practice but sees it more as an exercise in patience. For Leo, however, it’s more than that. It’s a reminder of balance. Of control. Of how even the smallest force, with the right guidance, can grow in the right way. And on nights when the pressure becomes too much, when he feels the weight of his role crushing him, he sits in silence before his little tree, allowing himself a moment to breathe, to reconnect with himself.
But love… love is different.
Leo doesn’t allow himself to fall in love easily. Not because he doesn’t want to, but because his mind simply doesn’t work that way. He needs to feel that his partner is more than just a fleeting attraction. He needs connection. Compatibility. A deep, unwavering understanding. And that isn’t built overnight.
That’s why, when he finally starts to realize that what he feels for you goes beyond friendship, the first emotion that floods him isn’t happiness.
It’s doubt.
And Leonardo shouldn’t doubt.
He always has answers. He always has a plan. But for the first time, he’s standing on ground where logic is useless, where he can’t break things down into a battle strategy. He can’t make a pros-and-cons list about his feelings. He can’t calculate every move the way he would in combat. And that frustrates him.
Because if he accepts it—if he acknowledges that his feelings are real—it means there’s something in his life that he can’t control.
And Leonardo hates not having control.
Leonardo isn’t someone who falls asleep easily.
Not because he doesn’t need to—his body demands rest just like anyone else’s—but because his mind never truly shuts off.
In the lair, when everyone else is asleep—when even Donnie has finally stepped away from his monitors, and Raph has stopped pounding the punching bag—Leo is still awake. Arms crossed, back stiff against the wall, gaze lost in the dim light of his room.
It’s in those moments of solitude that his mind betrays him.
When he tries to dissect what he feels, to categorize it, to put it into some kind of logical order. Because he’s always in control. Always.
And this… this shouldn’t be any different.
He’s not impulsive like Mikey, letting himself be carried away by every emotion without a second thought.
He’s not a ticking time bomb like Raph, ready to explode at the most unexpected moment.
He’s not even like Donnie, obsessively analyzing every variable to the point of overload.
He is Leonardo.
Leader. Warrior. Strategist.
And there is nothing he can’t control.
So if he has reached the conclusion that what he feels for you is real, then he will take the reins.
It won’t be difficult.
It shouldn’t be difficult.
He will force himself to keep everything in place, to act with precision. His glances will linger just a second longer—but not enough to be obvious. His words will be measured, carefully chosen, but still carrying his usual composed tone. He will make small, almost imperceptible changes.
Like making sure you walk on the safer side of the street.
Adjusting his stance subtly to block the wind when you’re on the rooftop.
Asking if you’ve eaten well—but casually, as if it’s not really important.
And the worst part? Unlike Donnie, who would give himself away with nervous fidgeting and stammered words, you will never notice.
Because Leonardo won’t allow you to notice.
All you’ll see is someone who has everything under control. Someone who watches you with the same intensity he reserves for his enemies on the battlefield, as if he’s calculating every single one of your movements.
But what he doesn’t want you to see is the opposite.
That inside, he’s nervous.
That his palms sweat when he touches you, when his fingers accidentally brush against yours.
That his pulse quickens when you get too close, and he has to remind himself to breathe normally.
That in every conversation, in every moment, there’s a small part of him afraid that one wrong step will ruin everything.
Because if there is one thing Leonardo could never forgive himself for, it’s losing what you’ve built together.
Not just losing you, but losing your trust.
And if that were to happen… how could he justify it?
How could he explain to himself that after a lifetime of making the best possible choices to protect those he cares about—this was the one he let slip through his fingers?
And when he finally allows himself to admit it—when he has broken through every mental barrier he imposed on himself, when he has analyzed every angle, when he has measured every consequence—Leonardo feels something inside him loosen.
For a moment, just a moment, it’s as if he has won the hardest battle of his life.
The weight on his shoulders dissolves, and for the first time in what feels like forever, he breathes deeply without the pressure in his chest tightening.
You are his.
Not in some shallow, possessive way, but in something deeper, more primal.
Like an instinct that has always been there, buried beneath layers of discipline and responsibility, waiting to be acknowledged.
And now that he has… there is no turning back.
But the peace doesn’t last.
Because almost immediately, another weight crashes down on him—heavier, inescapable.
Before, his burden was uncertainty.
Now, it is certainty.
Now that he has you, he must protect you.
With everything he has.
Not just from the dangers of the outside world—but from himself.
Because Leonardo cannot afford to fail.
And even though love is uncharted territory—a battlefield he has never stepped foot on—he demands perfection from himself.
To be the ideal partner.
To give you exactly what you need before you even ask.
To measure every word, every gesture, every decision.
To make sure you never have to question if he is enough for you.
Because he has to be.
He is Leonardo.
And Leonardo does not fail.
But there is a problem.
Because you don’t want the flawless strategist.
You don’t want the leader who is always in control.
You don’t want the polished, calculated version of him.
You just want Leo.
The Leo who watches sci-fi shows but would never admit to liking them.
The Leo who pretends he doesn’t enjoy messing around with his brothers, but secretly loves the rare moments when he catches Raph off guard or makes Donnie roll his eyes.
The Leo who tends to his bonsai trees with quiet devotion because, though he never says it out loud, they reflect his philosophy: patience, growth, balance.
And that is a terrifying concept for him.
Because showing you that side of himself means lowering his guard.
It means allowing you to see what’s underneath the armor.
The boy who gets frustrated.
Who sometimes doesn’t know what to do.
Who fears he won’t be enough.
That side of him—no one has truly seen it.
Not even his brothers.
But you… you want to see it.
And the road to him letting you in will be a long one.
Because accepting that you love him for who he is—not for what he represents, not for what he does, but for his very essence—is the hardest test Leonardo has ever faced.
Leonardo believes he has everything under control.
That he can handle his emotions the way he handles a katana: with precision, with discipline, with absolute mastery over every movement.
But you…
You are a challenge unlike any other.
Because while he struggles to keep his composure, while he measures every word and makes sure not to take a wrong step, you simply are.
You don’t need strategies or plans. You don’t analyze every interaction as if it were a life-or-death mission.
And that unsettles him.
Because deep down, Leonardo doesn’t know how to be loved.
He knows how to protect. He knows how to fight. He knows how to sacrifice himself for others.
But when it comes to receiving love… that’s where the conflict begins.
He appreciates that you’re not overly affectionate with him.
That you don’t suffocate him with displays of affection that would make him uncomfortable, that would force him to lower his guard all at once.
But at the same time, he dies when you take his face in your hands and kiss him.
At first, he goes completely still, trying to process it, trying not to lose control.
But the moment you feel his breath hitch, the moment you notice the way his fingers grip your waist tighter than he probably meant to—you know he’s falling.
And the worst part is that he hates it.
Because Leonardo shouldn’t let himself go.
He shouldn’t forget the weight on his shoulders or allow something as simple as a kiss to make him feel lighter—as if, for just a moment, the world didn’t depend on him.
But he does.
And it frustrates him.
Because he’s supposed to be the unshakable fortress.
He’s supposed to be untouchable.
And yet, here he is.
With his heart pounding too fast.
With his mind completely blank.
With you stealing his control with just a simple touch.
It sounds contradictory.
Because it is contradictory.
But Leo is a contradiction.
Because while he says attachment is a weakness, he holds you tighter when you try to pull away.
Because while he insists emotions cloud judgment, he stays awake until dawn thinking about what he feels for you.
Because while he tries to convince himself that his duty is more important than his happiness, he wonders if, just this once, he can have both.
And that is the real battle.
Not against an enemy.
Not against an external threat.
But against himself.
Because loving you means lowering his guard.
It means trusting that, even if he doesn’t have everything under control, you’ll still be there.
It means accepting that love isn’t a problem to solve, nor a responsibility to bear.
It’s just… love.
And no matter how hard he fights it, no matter how much he tries to convince himself he can keep his distance, there is one truth he cannot deny:
You are the only person in the world who can make Leonardo stop fighting.
Leonardo isn’t someone who takes intimacy lightly.
For him, physical touch isn’t just an act. It isn’t just a moment.
It’s an offering.
And he doesn’t give himself away so easily.
Not because he’s afraid—or at least, he’d never admit it.
But deep down, there’s an unease that eats away at him.
His size. His strength. His biology.
You’re human. Fragile in comparison.
And even though he knows you’re strong, that you wouldn’t do anything unless you were absolutely sure, his protective instincts won’t allow it.
It’s not just about protecting you.
It’s about himself.
His own control.
Because control is the one thing he’s always had.
Ever since he took on the role of leader, ever since he understood that his life wasn’t his own but belonged to those who depended on him, Leonardo learned to restrain himself.
To hold back.
To be the balance in the midst of chaos.
But you…
You make him lose that balance.
And if he allows himself to let go, if he allows that wall to crumble, he fears what might happen.
Because to Leonardo, intimacy isn’t just physical pleasure.
It’s a connection.
It’s binding his soul with yours.
It’s giving you a part of himself that no one has ever seen before.
And that is the real danger
Because if he gives you that—if he allows himself to feel you, to touch you, to love you on such a profound level—
Then there’s no going back.
He knows he could become addicted.
That the moment he lets go of the weight on his shoulders and focuses only on you—on your body beneath his, on your breath hitching, on the way you say his name—
Everything else will fade away.
And Leonardo cannot afford to forget his duty.
But… what if, just this once, he could?
What if, just this once, he could be Leo and not the leader?
If he could forget the world for a few hours—lose himself in you, in the warmth of your skin, in the way you look at him as if he’s more than just a warrior, more than just a responsibility, more than just a soldier trained to sacrifice everything.
If he could simply be yours.
That… that is what truly terrifies him.
Because if he tastes it once, he knows he’ll want it again.
And again.
And again.
Until there is nothing left of the fortress he has so carefully built.
Until there is nothing left of the perfect leader his brothers need.
Only him.
Only you.
Just two souls bound together—no rules, no duties, no limits.
And though he tries to convince himself he can resist…
He knows that, eventually, he will fall.
But Leonardo knows he’s not ready.
That he can’t let it all go—not yet.
Because if he does, who will bear the weight of the world in his place?
If he falls, his brothers fall. If he allows himself to be selfish, even for a moment, everything he has built could collapse.
So he waits.
He waits for you to understand.
To understand that there are things he still cannot give you, no matter how much he desires them.
But that doesn’t mean he gives you nothing.
Something just as intimate, just as addictive.
Vulnerability.
Not with his body, but with his soul.
So when night falls, when the world goes quiet and there is no one but the two of you, he lets you see beyond the barrier.
He lets you step into his sanctuary.
He pulls out the blankets he keeps tucked away in the back of his closet, the ones with the worn-out Rebel Alliance logo, and hands them to you without a word.
He lets you see the space-themed pillowcase he would never admit he still uses.
And then, in the dim glow of his room, when there are no more distractions, no more responsibilities, you talk.
Not about strategies. Not about training. Not about what is expected of him.
You talk about everything and nothing all at once.
About stars and distant galaxies.
About the Star Wars episodes he never gets tired of watching.
About the times he wondered if his destiny was already written or if he could take a detour.
And it’s there, in those organic conversations—unplanned, uncalculated, imperfect—that you witness something few have ever seen:
Not the leader.
Not the eldest brother.
Just Leo.
And then, when sleep finally claims you, you curl up against his chest—no fear, no hesitation.
Your breathing slows, steady and peaceful.
Your warmth seeps into his skin.
And Leonardo, the one who never lets his guard down, the one who is always on alert, stays still.
Feeling.
Listening.
Your heartbeat, syncing with his.
Nothing separates you but a thin layer of skin.
And for the first time in a long time, he forgets.
Forgets duty, weight, sacrifice.
Forgets that he must be strong, that he must be everyone’s shield.
Because in this moment, there is only you.
