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Hi there may i request usopp x strawhat!reader? (fem!reader too) For the scenario i want something like them going on their first date together? Maybe somewhere along the way the two of em try to avoid the Marines during the date hehe,, i would like it to take place at post timeskip please tysm in advanced ! 💗

Troubled Date

usopp x reader

a/n: thank you for this request, it was really fun to write ♡

words count: 1.1k

tags: fluff, romance, first date

masterlist || ao3 || ko-fi

The Sunny is docked at a lively island town, filled with colorful markets, busy streets, and the smell of grilled seafood in the air. It’s the perfect place for a date, or at least, that’s what Usopp tells himself as he waits for you at the edge of the ship.

“Okay, Usopp, you got this,” he mutters, taking deep breaths “It’s just Y/N. Y/N, who’s been my crewmate for years. Y/N, who—who looks really cute today.” He swallows hard when he sees you walking toward him, wearing a bright smile.

“Ready to go?” you ask, tilting your head.

“Pshh, of course!” Usopp straightens his back “This is gonna be the best date ever! A legendary date! People will tell stories about it for generations!”

You giggle “Then let’s make it a good one, great warrior.”

He turns red but quickly clears his throat “Ahem! Yes! Let’s go!”

The two of you step off the Sunny and into the town. The streets are full of life, merchants selling trinkets, children running around, and street performers juggling flaming torches. Usopp’s eyes shine with excitement.

“Ohhh! Look at that!” He points at a booth selling deep-fried snacks “Let’s start with food! You can’t go on an adventure on an empty stomach!”

“I thought this was a date, not an adventure” you tease.

He grins “Same thing!”

The two of you buy some snacks and walk through the marketplace, enjoying the sights and sounds. Everything seems perfect, until Usopp suddenly freezes, his eyes wide in horror.

“Uh-oh.”

“What?” you ask, mouth full of food.

He slowly turns to you “Marines. Over there.”

You peek over his shoulder. A group of Marines is walking through the crowd, scanning faces. They don’t seem to have noticed you two yet, but they’re getting closer.

“What do we do?” you whisper.

“Hide! Quick!” Usopp grabs your hand and pulls you behind a fruit stand, both of you crouching low.

“Why do we always run into Marines at the worst times?” you whisper, pressing against the crates of apples.

“It’s the curse of being too cool” Usopp whispers back.

You roll your eyes but smile. The Marines stop near the stand, talking to the merchant. You and Usopp hold your breath.

“Hey,” he murmurs, voice suddenly soft “I, uh… I’m glad you came today. I was really nervous.”

You blink in surprise, then squeeze his hand “Me too.”

He turns bright red.

Before you can say more, a loud CRASH echoes through the market. You both peek around the corner and see Luffy at a food stall, arguing with the owner, his face stuffed with meat.

The Marines immediately turn toward the noise.

“Oh no” you and Usopp say at the same time.

“There! That’s Straw Hat Luffy!” one of them shouts.

Usopp’s grip on your hand tightens “Oh no, oh no, oh no—”

“RUN!” you yell, yanking him in the opposite direction as the Marines push through the crowd.

The two of you weave through the busy marketplace, dodging fruit carts and leaping over barrels. Usopp almost trips over a stray chicken, but you keep pulling him forward.

“Why does this ALWAYS happen?!” he cries.

“Because we’re pirates?” you laugh breathlessly.

“I just wanted a normal date!”

“You expected NORMAL?! On a date with me?!”

“…Okay, that’s fair.”

Behind you, the Marines shout orders. You spot an alleyway between two buildings and pull Usopp into it. The two of you press against the wall, panting.

The sound of boots stomping on cobblestone grows louder. Usopp peeks around the corner and immediately pulls back, eyes wide.

“They’re close” he whispers.

You glance upward and spot a wooden balcony above you “Up there!”

Without thinking, you grab Usopp’s waist and boost him up. He yelps, flailing before grabbing onto the ledge.

“H-hey! I’m supposed to be the one protecting you!”

“Less talking, more climbing!”

Usopp scrambles onto the balcony and reaches down for you. You grab his hands, and with a strong pull, he hauls you up, though he nearly topples over in the process.

“Phew,” he sighs, wiping his forehead “That was close.”

You both sit on the balcony floor, catching your breath. The Marines run past below, completely unaware.

For a moment, there’s silence. Just the distant chatter of the town, the cool breeze, and the two of you, still holding hands.

Usopp realizes it first. His face turns red “A-ah! Uh—”

You laugh, giving his hand a squeeze before letting go “Thanks for pulling me up.”

His heart is beating way too fast “A-anytime.”

You both sit there for a moment, looking out at the town. The sun is starting to set, casting a golden glow over everything. Even after all the chaos, just sitting next to you feels nice.

“…So, this wasn’t exactly the date I planned” Usopp admits.

You tilt your head “Oh? And what was the plan?”

“Well,” he starts, rubbing the back of his neck, “I was gonna take you to a nice restaurant, impress you with my amazing storytelling, maybe buy you a cool gift—y’know, romantic stuff.”

You smile “This was fun too.”

His eyes widen “R-really?”

You nod “Running from Marines together? That’s a real Straw Hat date.”

Usopp stares at you for a second before bursting into laughter “Okay, okay, you have a point.”

You stand up and offer your hand “Come on, let’s find the others before Luffy causes more trouble.”

He takes your hand, smiling “Yeah. But, uh…” He hesitates. “Maybe we try another date next time? A real one?”

You squeeze his fingers “I’d like that.”

His face burns red, but he grins, heart pounding in the best way possible.

You’re about to turn when Usopp suddenly tugs on your hand, stopping you. His expression is serious for once, though his face is still pink.

“…Wait.”

You blink “What?”

He hesitates for a moment, then takes a shaky breath “I, uh—before we go, I just…”

Then, before he can overthink it, he leans forward and presses a quick, warm kiss to your lips.

It’s short, barely a second, but it leaves you completely frozen.

Usopp pulls back, looking like he might pass out. His eyes dart everywhere except at you “S-sorry! I just—! I thought—! B-but if that was too much, I—!”

You cut him off by grabbing his scarf and pulling him in for another kiss, this one slower, softer. He lets out a tiny, surprised squeak before melting into it, his hands awkwardly hovering before resting on your waist.

When you finally pull away, his face is an impossible shade of red “Oh.” His voice cracks “Oh.”

You smile, brushing your fingers over his “I really, really liked this date.”

He sways a little, dazed “…I think I did too.”

You laugh and take his hand again “Come on, Romeo. Let’s go before the others start looking for us.”

Usopp stumbles after you, still red-faced but grinning like an idiot.

Maybe this date didn’t go as planned.

But honestly?

It turned out way better.