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Chapter 5 - Chapter 5. Dating Lessons from a Chaotic Angel

The shopkeeper finally blinked and tried to play it cool.

"Wow. Bold. Also—you didn't even ask my name. Do you hit on strangers like that all the time?"

Elinalise froze. "Uh… yes? I mean—no. I mean—what's your name?"

She smirked. "Isola. Remember it. And meet me tonight at the bar around the corner—The Silver Lantern. Sundown."

"Coolcoolcool," Elinalise said, doing the world's worst attempt at a smooth nod.

The angel gave a tiny thumbs-up like a proud, chaotic coach.

Elinalise cleared her throat. "Also—we, uh, need stuff. Water. Food. A place to sleep that isn't, like, the floor."

Isola slid into shopkeeper mode. "Two canteens, dried jerky, trail bread, a cheap bedroll." She stacked items with scary efficiency. "For sleeping: The Sleepy Griffin Inn—two streets over, near the candle maker. Tell them Isola sent you; they'll knock a few coppers off if you don't break anything."

Elinalise tried to be flirty while paying. It went… not great.

"So, uh… thanks. Your… shelf organization is… hot?"

Isola stared.

The angel lifted a finger like she was about to rewind time.

Elinalise panicked. "I mean your hair. Your style. It's cute. Really cute."

Isola's mouth twitched into a real smile. "Better."

Money changed hands. The sack of supplies looked heroic; Elinalise did not.

"See you at sundown?" Isola asked, pretending it was casual and failing in a cute way.

"Yeah. I'll try not to trip on my own face before then," Elinalise said.

"Please don't," Isola said. "I'm short on bandages."

They headed for the door. The angel leaned in, whispering, "If you mess up the date, I'm rewinding. I am not wasting that smile."

Elinalise nodded, very serious. "Copy. No creepiness. Compliment hair. Do not mention shelves."

They stepped back into the street: supplies secured, inn target acquired, date locked in.

Low effort. High chaos. Progress.

The streets glowed in amber and violet as the sun finally dipped behind the rooftops. Elinalise kept her hood low, the loose folds of her coat hiding her figure. Isola walked beside her, casual but graceful, the rhythm of her steps oddly hypnotic.

Above them — or perhaps beside them — floated the angel, invisible to all but Elinalise. She looked utterly different from her usual serious self: scarf tied back, wings folded lazily, a drink already in hand. Vacation mode.

"Lucky for you, I'm even working on vacation," the angel murmured in Elinalise's ear. "Lesson one: flirting isn't just words. Tease, charm, and be funny. Humor is the bait. Keep her laughing, keep her curious."

Elinalise muttered under her breath, "Flirting lessons from an angel. Of course."

"Shush," the angel whispered. "Step one: light negging. Step two: jokes. Step three: let me feed you lines while you nod and pretend they're your own."

Inside the bar, the warm lamplight spilled over wooden tables, murmurs of patrons mixing with the scent of wine and woodsmoke. Elinalise followed the angel's whispered instructions like a soldier obeying orders.

"Ask her if she always walks this slow, or if she's worried her beauty will blind someone if she hurries. Then add a joke about the lanterns being jealous."

Elinalise leaned in slightly. "You always walk this slow, Isola? Afraid your beauty might blind someone? Or the lanterns are just jealous?"

Isola smirked, eyes narrowing. "Careful. I could say the same, but your ego might start floating off without you."

"Good! Now throw in a joke about yourself. Self-deprecating humor makes them relax."

Elinalise laughed, a little awkwardly. "Well, I am kind of known for making a mess of perfectly good charm."

They sparred like this for several rounds — teasing, joking, poking and prodding — while the angel continued to feed lines, murmuring tiny quips about when to joke, when to pause, when to make it light.

After a few drinks, Isola set her cup down and tilted her head. "You know," she said slowly, "you could… accompany me to my house. If you're not too busy verbally sparring with me all night."

Elinalise hesitated, then felt the angel's nudge.

"Say yes, but make it sound like you're indulging her curiosity, not desperate. Humor can carry you here."

Elinalise grinned. "Well… I suppose I could make the time. I promise not to trip over my own cleverness."

Isola's smile widened, half challenge, half invitation.

"Perfect," the angel whispered, voice dripping with mischief. "Lesson two starts at her door. And remember — humor first, awkward charm second."

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