I aim to see how Calypso and Leo's interaction might have gone had they not been become romantic. Given that those chapters cause me physical pain to read, I will not be following them exactly, but I have kept Calypso's original reaction effectively the same (though toned down) and will include a few details or events from canon.
Disclaimer: Not mine, as evidenced by the fact that platonic Caleo is only fanfiction.
Calypso was pulling weeds—again. Really, you'd think after millennia of sitting in the literal middle of nowhere, a few of the heroes would have showed up with eternal weedkiller. But no, no weedkiller for her. Instead she got to pull weeds, host a mindboggling wonderful hero, watch him sail off forever, then go back to pulling the little green demons out of her garden. Then repeat—over—and over—until she was ready to tear her own hair out.
She was pondering this cycle, as per usual, when she heard the crash.
Crashes were, as a rule, fairly unusual in one respect: how often they happened. Time was liquid on Ogygia, but she'd learned to concentrate on the days, so she knew that sometimes it was only a week between heroes, and other times it was months or years or decades, totally irregular. But in every other respect, the crashes were exactly the same. She stood slowly, dusted the dirt from her hands and knees, and with a sigh made her way down to the beach.
The day was usual for a crash as well. Whichever god had enchanted Ogygia had had a particularly nasty plan: Crash Days were always gorgeous, what with the clear skies, touch of breeze, warm sun sparkling just so on the seawater. There was no reason for a recently marooned man to hurry away; he'd stay just long enough. And then he'd leave. Oh, goodie. She just couldn't wait to have it happen again. After all, those weeds wouldn't pull themselves.
The cool grass faded into warm sand, and her feet crunched and slipped in it as she made her way down to the shoreline. The men always ended up in the same place; it wasn't like it took a lot of thinking to guess where to look. But as she neared the water, she was surprised to find she didn't see anyone. She rose on her tiptoes and swiveled. Where was her visitor?
Then a lump of sand shook, and Calypso's eyebrows jumped as she realized that what she had thought was a particularly dingy spot of mud was actually someone's rear end in khaki. The bum wiggled from side to side, and then its owner fell over backward, landing at her feet with a muffled thud and a loud Spanish swearword.
She stared down at the boy (not even a man), and he stared back up at her with his hair in the sand. He was Spanish of some variety, guessing by his profanity and tan complexion. Short, no more than 5'6", and with the approximate physique of a handrail. Pimples dotted his brow and chin, and what skin was visible was splotched with dirt, blood, and engine oil. The arch of his eyebrows and the point of his ears made her think of firecrackers and trapdoors.
Say it with her: Oh, goodie.
But at least he was unusual.
"You're pretty," he blurted.
Well, relatively speaking.
He continued: "Did it hurt when you f—"
"No." She tried to pass her sigh off as a simple exhale. Unlike weedkiller, pickup lines were in regrettably high supply among most heroes who visited Ogygia. You'd think save-the-world types could at least save their sense of humor at the same time. "Who are you?"
The scrawny boy scrambled to his feet. "The man of your dreams!" he proclaimed with a grin, spreading his arms as wide as he could. "But more specifically, Leo Valdez."
She really did sigh this time, sending a reproachful look up to the sky. "Fabulous," she gritted out, knowing full well that Zeus could hear her. Friendly thunder crackled in the clear sky, but the obnoxious boy—Leo—didn't disappear.
"Are you alone out here?" Leo was glancing around the beach; apparently the surrounding silence had just now registered. "That must suck—Oh." The reason came to him and his face cleared, though sadly this was only metaphorical; the unfortunate case of acne still remained. "You're that girl named after Caribbean music!"
She stared at him, unamused. I've never heard that one before, she thought in her Bright And Sarcastic voice. "The name you're looking for is Calypso. And, in case it matters to you, I'm a goddess."
"That makes sense, since you're as beautiful as Aphrodite." His eyebrows waggled.
She squeezed her eyes shut for a count of one, two, three, four, five. Maybe when she reopened them, her high levels of patience would be enough to get him sent back to wherever he'd come from.
She opened her eyes. Nope. He still stood there in the sand before her, his smile wider than she would have believed possible without seeing it in person.
"Nice to meet you, Leo," she said, the Bright And Sarcastic tone slipping from her mind to her tongue. Whoops, she thought in the same tone. "I'm sure you have places to be—"
His smile lost a few teeth, not that she particularly cared. They always had places to be, these heroes.
"—so just say 'I want to leave Ogygia,' and we can both be out of each other's hair."
"We do both have fabulous hair," Leo said, running his fingers through his curls in an attempt to either flirt, brush it for once, or get back to Silly Mode. Or a mix of all three.
She waited.
"It was what? I want to leave Squeegee-ah?"
"Oh-jee-jee-ah," she enunciated, crossing her arms. Rude enough to show up dirty and unattractive. He didn't have to make fun of her and her island's names on top of it. She didn't ask for him to come here.
"I want to leave Oh-jee-jee-ah," he repeated, but the tide pulsed at exactly the same rate and no raft appeared in the wake of any waves.
"Try it again," Calypso suggested, her nails digging into her forearms. If the Olympians didn't give her this . . .
With a slightly disgruntled look in her direction: "I want to leave Ogygia." He certainly sounded like he meant it.
Still, nothing.
She sighed, deep and hopeless, and turned on her heel. "Come on," she grumbled, trudging back up the path to the grass. Leo followed, his loping puppy feet going crunch crunch crunch in the sand. He chattered—mostly bad pickup lines—and she responded as monosyllabically as she could without completely ignoring him.
Then she got to her cave and shut the curtain-door in his face.
"I'll just hang out . . . out here, then," Leo shouted.
She pressed her fingertips to her temples and let them drag down her face.