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Jerro

Action Comics #269: “Supergirl’s First Romance!”
 

What I like:

Jerro the mer-boy somehow manages to wear a superhero speedo over his mer-tail. He’s also got knees poking out and his tail bends like human legs in a mer-tail suit! And what’s up with his shirt and belt?

What’s messed up:

As a young female counterpart of Superman, of course Supergirl’s first love interest is a male counterpart of Superman’s college sweetheart, mermaid Lori Lemaris. In his first appearance, his only purpose is to be a love interest to Supergirl and there’s not much else to his character.

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Dick Malverne

Action Comics #256, “The Great Supergirl Mirage!”
 

What I like:

Not much really

What’s messed up:

Dick Wilson was a boy at the orphanage that acted as Supergirl’s version of Lana Lang.  Before people knew there was a Supergirl, Dick was this insane kid who super suspected Linda Lee to be Supergirl. His first attempt to expose her was to throw an incredibly life-like dummy of himself filled with chemicals that would burst into flames if a superperson uses x-ray vision on it. This is far too elaborate for a first try. He returns into the comics after he gets adopted with his new name, Dick Malverne. He’s grown up a little and is no longer crazily suspicious of her. He becomes Linda Lee’s recurring boyfriend, but that doesn’t stop her from smooching with her other love interests.

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Brainiac 5

Action Comics #276  “Supergirl’s Three Super Girl-Friends”
 

What I like:

Brainiac 5 is the only one that matters! He’s the most adorable blonde green-skinned boy from the future. 
Unlike Jerro, Brainy’s his own character. He’s a member of the Legion of Superheroes, a group of super-teenagers in the future. He’s sort of one of the smartest beings in the galaxy, so I imagine his teenage teammates must all feel like idiots to him.
The silver age version of him is the saddest most apologetic boy whenever he thinks of his ancestor, Brainiac, who destroyed Supergirl’s home world, Krypton. 
He’s so in love with Supergirl and would do anything for her. 

What’s messed up:

They meet in Brainiac 5’s first appearance. The beginning of the comic is all about how Supergirl wishes she had female friends to talk to. So three girl superheroes from the future come to hang out with her and take her on a visit to the future with the rest of the Legion. But the moment Brainiac 5 appears, you don’t see those girls again. They are forgotten and the story shifts to being all about Supergirl getting another boyfriend.

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Superman

What I like:

Well… I love Superman. I don’t like what the writers have him doing here…

What’s messed up:

Superman is an adult grown man and Supergirl is his 16 year old kid cousin. 
When she arrived on Earth, he decided the best place for her is at in the orphanage. She was strictly not allowed to get adopted or reveal her existence as Supergirl, Superman’s “secret weapon.” And when she reveals herself to Krypto, Superman exiles her to an asteroid! Often times Supergirl worries of making Superman furious. 
And then there’s this issue, “Superman’s Super-Courtship!” where Supergirl tries to get Superman to hook up with Helen of Ancient Troy and then Saturn Girl from the future Legion of Superheroes. He responds to this by going off into cousin marriage laws that keep him from marrying her? At once, Supergirl giddily finds an adult super duplicate of herself on another planet who Superman immediately falls in love with!
And then on top of all that, Supergirl’s secret identify’s initials are LL! Even though I know she names herself Linda Lee, I still suspect that it’s Clark’s fault due to his super obsession of LL names.