First Headcanon!
Different Eras Leon S. Kennedy x Reader
How the different eras of Leon would say he cares/loves you.
Warnings: I don’t think there is any for this, but if there is, please let me know!
Word Count: 1,638
A/n: Use of Y/n (Your Name)
Resident Evil 2 Leon (1998):
To me, RE2 Leon is earnest, a little awkward, and sincere. He hasn’t built the emotional armour yet. When he admits his feelings, it would sound like he’s figuring it out as he says it:
“I didn’t come to Raccoon City expecting to feel anything like this. Honestly, I was just trying to survive. But every time I see you, it’s like the noise quiets down for a second, and I know this is a terrible time to say it — the worst, probably — but I don’t want to walk out of here and pretend this never happened, that.. that kiss never happened… You matter to me, Y/n. More than I can explain without sounding stupid. I just… really like you… if we make it through this, I’d like the chance to see where that goes…”
Resident Evil 4 Leon (2005):
RE4 Leon is more confident, a little sardonic and more emotionally guarded. Though, when he’s serious, the humour drops and what’s left is direct and steady:
“I’ve been doing this long enough to know getting close to someone is a risk. Usually I keep things simple…finish the mission, don’t look back. But you make that harder than it should be. Every time I tell myself to keep my distance, I end up wanting to be closer instead. And I’m done pretending that’s just coincidence. I care about you, Y/n. Not as a distraction, not as a passing fling. You matter to me, and whatever comes next… I want you in it.”
Infinite Darkness Leon (2006):
Infinite Darkness Leon is more closed off here I think, considering this version of him is fresh from RE4 by a year. He carries more trauma, while circling the word love without quite being able to land on it. He’s masking the weight of it with dry humour, but still letting the truth slip through:
“You ever notice how I can walk into a room full of bio-weapons without my pulse changing, but this conversation’s got me hesitating? That’s… new. I’m used to keeping things simple… job first, everything else somewhere far behind it. Keeps people safe, keeps me functional. But you’ve got this habit of standing right in that space I keep trying to clear out. And no matter how many times I tell myself it’s smarter not to feel this much about someone, you don’t exactly make it easy. I care about you, Y/n, more than I’m comfortable admitting, and I’m already saying more than I planned to. Just—” a quiet exhale, a crooked half-smile “—if I start acting like I’m trying to stick around, it’s not by chance. That’s me… choosing you… In my own way.”
Degeneration Leon (2008):
Degeneration Leon is calmer and more grounded. He’s more experienced, gentle in a way he doesn’t advertise, and protective without being overbearing. When he admits feelings, it would sound measured and sincere:
“After everything I’ve seen, I try not to take the people in my life for granted. Things change too fast and people disappear. But somehow, you’ve become the part I look for when the dust settles. Being around you feels… normal. And I didn’t realize how much I needed that until now. I’m not the best at this, Y/n, but I want you to know I love you. Not just because of what we’ve been through, but because of who you are and I’d like to keep you close, if you’ll let me?”
Damnation Leon (2012):
Damnation Leon is more jaded and politically worn down. He’s sharper, pragmatic, and a little cynical, but still deeply loyal. When he opens up, it sounds like someone who’s seen too much to romanticize it, yet can’t deny what he feels:
“I’ve spent enough time in war zones to know attachments complicate things. They give the world leverage, so I got good at telling myself I don’t need them. It’s cleaner that way. But every time I check in and hear your voice, that whole argument falls apart. You’ve got this way of… cutting through all the chaos, makes the rest of it feel distant for a minute, and yeah, that probably means I’m in deeper than I planned…”—he looks at you, “Don’t look so surprised, I’m still figuring out how to say it without sounding like an idiot. Just know this: what I feel for you isn’t temporary, and it’s not casual. If I’m fighting this hard to come back in one piece, it’s because there’s someone waiting I—” a brief pause, a deep, self-aware huff “—care about more than I’m supposed to. You included. Especially you.”
Resident Evil 6 Leon (2012-2013):
Poor RE6 Leon, he is so exhausted, guilt-ridden, and older in a way that shows, but he’s also fiercely steady. When he admits feelings, it comes out rough and unpolished, like he doesn’t have the energy to dress it up:
“I’ve buried enough people to know how this usually ends. Every time I let someone get close, the world finds a way to test it. Then I keep telling myself distance is the smart move, it’s safer for everyone. But then I look at you, and all that logic starts sounding like an excuse. You’re… the one thing in my life that doesn’t feel like a battlefield. And I’m not good at saying this — hell, I’ve been dodging it for a while — but what I feel for you isn’t something I can file away with the rest of the job. I love you, Y/n. More than I’ve let on, enough that it scares me a little, and after everything, that’s about as honest as I know how to be.”
Vendetta Leon (2014):
Vendetta Leon is at his lowest here… grieving, self-desprecating, carrying survivor’s guilt, and trying to sound casual even when he’s confessing something that terrifies him. He’d lace it with his usual humour to keep from completely unraveling:
“I’ve been telling myself for a long time that I work better alone, fewer variables, fewer ways for things to go wrong, and considering my track record… that’s not exactly paranoia. But then you keep showing up in my head when it gets quiet, and I hate how much that cuts through all the excuses. You make it hard to keep pretending I’m built for this empty, mission-to-mission routine. I’m not great at… saying what this is, feelings were never in the training manual. But when I think about the future — yeah, I know, scary concept — you’re there. And that’s not an accident. I want you, Y/n. More than I’ve let myself want anyone in a long time. If that sounds like I’m dancing around a word we both know is there…” a tired half-smile “…chalk it up to professional hazard, but it’s real. You’re real to me.”
Death Island Leon (2015):
Death Island Leon definitely feels more settled than his Vendetta version. He’s still carrying that weight, but he’s more stable, more self-aware. He’d sound quieter, like he’s choosing his words carefully, with a flicker of sarcasm to keep it from getting too heavy:
“You know what the worst part about doing this for so long is? You start thinking you’ve seen every version of how things can fall apart. Makes it easy to keep people at arm’s length. Call it experience. But you slipped past that somewhere along the way, and now every time I try to convince myself that keeping distance is the smart play, I hear how ridiculous it sounds. Because the truth is… you’re the part of my life that still feels solid. I’m not good at big speeches, and I’m definitely not good at saying that word you’re probably waiting on.” a faint, self-conscious smirk “But if there’s anyone I’d trust with my back — and everything else that comes with me — it’s you. I need you, Y/n. Deep enough that it’s not going anywhere. Guess that’s my way of saying… you matter more to me than I ever planned on letting anyone matter.”
Resident Evil 9 Leon (2028):
(A/n Since it’s the end, I made it a little one shot for this version of him 😗)
RE9 Leon is a silver fox and with his age there’s more wisdom. From the trailers of RE9 my guess is that he’d likely be emotionally mature, but still scarred. He’s someone who finally accepted that love is a risk worth taking and doesn’t dance around it anymore. He’ll confess in a way that’s quiet, direct, intimate and stripped of theatrics. Less circling, more certainty, the humour will still be there, but softer, like a pressure valve and not a shield:
He studies you for a second before he speaks, like he’s committing the moment to memory. Then a small smirk tugs at the corner of his mouth — soft, a little tired, but real. His hand comes up to rest over yours, thumb brushing lightly against your knuckles, grounding himself as much as you.
“I’ve spent most of my life acting like there’d always be time to say things later, there usually wasn’t, so I’m not making that mistake with you. I know what this job costs, I know what it’s taken from me. And somehow, after all of it, you’re still the thing I want to come back to. Not out of habit, not because I’m afraid of being alone.” His gaze steadies on you, the smirk fading into something more open. “Because it’s you. I love you, Y/n. And I’m done pretending that’s something I need to apologize for.” His thumb shifts in a small, absent stroke against your skin. “If the world wants to make that complicated… it can get in line.”