Alright I'm giving a class about Caleo then https://t.co/xiIkAOpzFZ 
First of all: yes, Leo keeps flirting with every remotely good looking girl he sees, and yes, he feels hurt when each one of them rejects him. But it's not just because he wants a relationship. He feels hurt because his deepest fear is to be rejected, by /anyone/, not just girls.
Leo's whole arc is that he always feels rejected, that he's the seventh wheel. That's what Nemesis told him in the beginning, and that's what he struggles with the whole series.
Leo wants to be part of a group, he's tired of running away from foster families to foster families; he wants to belong. He's not jealous of Percy for Calypso, he's jealous of him for being popular, for being so comfortable in situations that are still new to Leo.
Given that this series is about accepting who you are as a person, accepting your differences because they make you stronger, realising that you're strong as who you are; it could have been a great lesson for Leo to learn that he didn't need anyone to complete him.
Leo who already had so much on his plate, being the most important of the seven, the most powerful according to Gaia, the one with the less self-confidence too; imagine if he had learnt to love himself as he is, to understand that he /is/ strong and that he does belong.
That would have made a great arc, exactly the kind of representation we deserve. You do NOT need a s/o to be complete, or to be accepted. You just need to be yourself, and it's good enough.
But instead RR chose to give us this lesson: if you're feeling like you don't belong, if you're afraid of being rejected, if you don't like who you are, if you desperately want a girlfriend........ then you'll find some long-lost beautiful goddess on an island and you'll be fine!
In PJO I had no major problem with Calypso (and I actually LOVE the adaptation of the original myth into the riordanverse, it's absolute genius). She was brave and smart in PJO, letting Percy go, accepting her fate and understanding what it means to be part of a family etc
But in Heroes of Olympus...... Well Calypso is a real dick to Leo. Right from the start. Did she have to be so harsh when Leo landed? Seriously?
I get that she's fed up of having demigods sent on her island for the sole purpose of getting her heart broken. But she didn't react like that when Percy landed, as far as we know? She literally chose to dislike Leo simply because he didn't /look/ good enough for her.
So Leo gets super hung up on her and makes her his number one priority - fine. So I get excited to have them in The Dark Prophecy anyway, see how they'll evolve as a couple and all. Boy, was I wrong.
Because let's be honest, their relationship is super toxic. Calypso is nothing but mean to Leo. I'm not talking about playful banter or anything, she's just /mean/. (According to Apollo, they fight often)
Then there's the fact that Calypso reduces Leo to jokes and being a mechanic. It's like she never appreciates Leo for who he actually is, and for what he's worth. She always complains about his love for machines and Festus.
Yes, I'm aware in the last extract they're fighting and all, but she's always like that.
And there's the fact that she keeps blaming Leo for losing her powers. He rescued her but she's frustrated about losing her powers, and somehow that's Leo's fault? How is that a healthy relationship?
She doesn't even do anything to built up Leo's self-confidence. There's no chemistry between them, not a drop. It's just banter, turning into real fights, turning into low accusations about lost powers, turning into Leo being hurt. End of chapter.
If it had been actually necessary to match Leo with someone, why did it have to be with Calypso? What leo needs is someone who can channel his energy into something productive and sees how great of a person he is, and reminds him of that. Calypso is none of those.
So yeah, Caleo is not a healthy relationship at all, and Leo deserved a far better arc than this one. The end
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