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1: Piper and Jason
It was naive to think that, after realizing that Jason wasn't who they thought he was, Jason and Piper wouldn't be together anymore. It was stupid, child-like naivety that Leo somehow had still clung to, until the two mentioned the words "dating".
It's not that he hated them together, per say. No, it wasn't that. Nor was it that he liked either of them, because he didn't. He tried that once, when he first met Piper and had seen boys falling on their knees to get near her, and when he met Jason (or the mistified version of him) and had seen the girls do the same. But, whatever he did, he couldn't see them like that.
No, his problem was jealousy.
He wanted nothing more than someone to hold him, to kiss him goodnight and not complain about the grease-stains on his clothes and the chappedness on his lips. But, every time he tried to look at someone the way people had looked at Jason and Piper, he'd fall short.
He hated that.
So, naturally, the naive part of his mind thought Hera-manipulation had caused a break-up, and he'd be on an equal playing field. He had no one else besides them, he was tired of being tossed aside for heated make-out sessions and dates. He hadn't anticipated them falling again.
Piper and her siblings would set him up on dates, with pretty girls who thought his building of the next Argo was the best thing since sliced bread. He went on date after date, with girls from a variety of cabins— Demeter, Hermes, Nike— and every one ended terribly. Well, not terribly, per say. He was amicable with everyone. But, they all ended the same:
"You're great, Leo, really—"
"I admire your dedication—"
"You've got a big heart—"
"I just think—"
"You spend all your time building—"
"I feel like you don't see me how I see you—"
He's heard it all. And every one ended with him sobbing on Piper or Jason's bed, with one of them rubbing his back softly, trying to reassure him.
"We'll find the right person for you," Piper would say, "We just need to figure out your type."
"Maybe you're into guys?" Jason suggested, "Lots of people in mythology had male consorts."
Leo looked at him through glassy eyes, "And how do you know that, Mr. Amnesia?"
Jason shoved his shoulder lightly, "I've been reading up trying to get my memory back while you're cooped away in your bunker."
"I don't think I'm into guys," Leo admitted, "But, I'll keep my eyes open."
Piper smiled, "That's the spirit, Leo. If you have your eyes for someone, just tell me and I'll help."
"Maybe now isn't the time," Jason said, "I mean, you are building an entire ship that flies. Maybe take a break from dating."
Leo rubbed his bloodshot eyes, "I just don't want to be alone again."
Piper wrapped her arms around his waist, pulling him in tight. "You won't be. You have Jason, myself, and your siblings. Focus on yourself for a bit, if you need to, and I'll be here to set you up when you're ready."
Problem was, Leo wasn't sure he'd ever be ready. But, he nodded anyway.
2: Percy and Annabeth
Even before he met Percy, he had been told that he and Annabeth were goals. They were the blueprint for every relationship—childhood rivals to best friends to lovers—and people gushed at their sweetness like they were the main characters in a romance novel. Even Harley, who was barely eight, had mentioned their relationship, saying that they're relationship was like one out of Disney (with cooler monsters and more explosions!).
Leo had thought he was ready to meet them. He had had ample amount of time to prepare himself, ample amount of warnings. Yet, still when he first saw that, his heart sank; anchoring him like the Argo II was anchored above head.
The way Percy looked at her while she ran across New Rome to him, the way he looked up at her when she judo flipped him, the way her face lit up in a way Leo had thought was impossible, it was a lot to handle.
He searched the Roman legion, hoping to find anyone who sparked his interest, but no one stuck out. Some people had hair cuts he liked, some had bright smiles or vibrant eyes, but it was akin to looking at a picture in a museum. Its novelty wore off after only a moment, leaving him looking for something else to catch his attention.
Yet, that something else never came.
Later on during the quest, when Percy fell into the depths of Tartarus for Annabeth, all Leo could think was, "Would anyone fall for me?" Literally and metaphorically.
And the truth was? He didn't really think so.
He also didn't really think he'd fall for someone else either.
3: Hazel and Frank
There was a brief moment when Leo thought he truly liked Hazel. Where he'd get to live out his knight-in-shining-armor dream and fight for her affection.
That thought was fleeting, though.
The way he looked at Hazel could never compete with the way Frank did. He couldn't describe it—the difference in their affections—but it was there. Something was different. One was right, proper, and the other was not. It was easy to pick out which was which.
It had been a joke growing up, Leo understanding machines rather than people, but slowly it was twisted into his reality.
As messed up as it sounded, even in his own his, he saw people as machines. Deep down he knew they weren't—people couldn't be fixed or programmed like machines—but Leo had the same affection he held for his automations that he did for his friends. And for Hazel.
It was almost a relief to find out Hazel wasn't truly attracted to him; just his appearance and the perceived personality she had constructed for him based on his bisabuelo. Just as it had been a relief that the girls he dated at Camp Half-Blood broke it off, and never him.
Gods, he was a mess, wasn't he?
+ 1: Calypso
Leo had almost found love in Calypso, worn her down with his charm and good looks, and he thought they'd be perfect.
Oh Hephaestus, were they anything but.
After dying and rescuing her, they traveled for months together, through thick and thin. And Leo liked spending the time with her, objectively she was a nice person (after you get past her prickly exterior), and everything Leo should have wanted in a girl.
A month on the road, flying over the Alps, Calypso tapped Leo's shoulder, and he turned around, so his back was against Festus's neck.
"You don't have to pretend to like me, Leo," she said, "It's okay, I can handle rejection. I'm sort of an expert on it."
Leo scrunched his nose in confusion, "I do like you?"
Calypso's laugh was a melody, one of irony and satire. "No, Leo, you don't."
"Of course I like you!" Leo repeated, more for himself. "You're pretty and smart and talented and everything I want in a girl. Of course I like you."
Calypso leaned forward and pressed her lips against Leo's, and Leo shuttered under the touch. Still, he responded, moving his lips against hers. It was weird, almost gross in a way, and he didn't particularly like it. But, everyone liked kissing the people he liked, so he made himself enjoy it.
Calypso pulled back. "How was that?"
Leo cocked his head, trying to put on a smile. "Great."
"You're a terrible liar."
"I'm—"
"Leo, you're a great person, you really are. But be honest with me, did you like that?"
"Not really," mumbled Leo.
Calypso's smile was a mixture of hurt yet understanding. "I thought as much. I've kissed enough men who haven't liked me back to know."
"Calypso, I can try again, maybe this time—"
"No, Leo." Calypso said sternly. "You can't make yourself like someone you don't. That isn't how life works. I like you, you don't like me, I move on. That's the way life works."
"You're leaving?" He hated the way his voice cracked.
"Move on," Calypso said, "Not leave. Like I said, Leo, you're a great guy, I've just got to learn to love you like a friend."
"What's the difference?"
"What?"
"Between loving someone as a friend and loving someone as a partner?"
Calypso thought for a moment, "You know, in Greek, we have different words to describe those, unlike English."
"Like in Spanish? We say 'te quiero' when we love something, or a friend, but 'te amo' for our close family and partner?"
"Sort of," Calypso said, "But these aren't ways to say I love you, but rather ways to describe your love for someone. What I feel for you is called Eros, or romantic and sexual feelings."
Leo's eyes widened, and he nearly fell off Festus, "You have sexual feelings for me? Like more than kissing?"
Despite her reddening cheeks, Calypso chuckled. "Right. But, that's besides the point."
"Wait, so people actually want to have sex with people?"
Calypso frowned, "Yeah, obviously, didn't you know?"
"No!" exclaimed Leo, "I thought that people just had sex to have babies or as something to do when you're sad and bored. Not something you actively seek out!"
"Sad and bored?"
"Like binge-eating," Leo reiterated, "Or watching your favorite show again."
Calypso's head spun, and Leo could see the gears spinning. That comforted him a bit. "No, it's not really like that."
"Oh," Leo scratched his head, "Learn something new everyday, I guess. What was the other type of love?"
"Philia," explained Calypso, "Platonic love, or not physical."
"Wait, physical? What do you mean by physical?"
Calypso didn't answer, instead looking down at the cascading mountains, "I think I'll break your mind if I tell you."
"I can handle it!" Leo said, "Baby, I've saved the world, one word isn't going to hurt me."
"Well," Calypso shut her eyes in thought for a moment before opening them again. "Eros is sort of physical. Like a throbbing, that's why people actively seek sex."
"You get that looking at me?"
Calypso shrugged, her face red, "Sometimes."
"And at other people too?"
"Sure."
"That's weird," Leo mumbled under his breath, almost afraid to be overheard.
"Not really, most people are used to it."
"Is that feeling all the time?"
Calypso shrugged, "Often enough. I assume you can't relate? Have you felt that way with anyone? A girl? Or a boy?"
"I'm sorry," Leo responded immediately. "I can try? Maybe I just need to think about it more?"
"You can't force it, Leo," Calypso said, "You can't make something out of nothing. You probably know that better than anyone."
Leo did know that. He was skilled in the art of creating something marvelous out of barely anything, but there was always a beginning. Never nothing.
"Friends?" Calypso said, holding out her hand.
Leo took his hand in hers, "Are you sure?"
"I can handle it. I've been dealing with it for thousands of years. Besides, I'm not cursed anymore, maybe I can find someone who likes me back?"
"I'm sorry."
"Stop saying that," snapped Calypso, "It's not your fault. We're friends, remember?"
Leo nodded, "Friends."
He turned around and guided Festus through the air.