Superman and family's entire romantic history

[Jackalope89]

For Jon Kent, would Kathy count, or is he still a bit too young for that just yet?

[Miles To Go]

For Jon Kent, would Kathy count, or is he still a bit too young for that just yet?

The two were openly flirting early on when Jon still lived in Hamilton, though I think they've cooled it since then.

[friendly-fire-press]

I think there was an Elseworld called 'The Dark Side' where Superman hooked up with Big Barda at the end (I'm not 100% sure tho, it's been many years since I read it)

[Slimybug]

Does anyone know what issue Superman supposedly falls for Cleopatra?

[marshal88]

cleo later ruled over the men of the jla with her magic staff and clashed with supergirl and batgirl.

[Slimybug]

Random question: Who is the Ruby mentioned earlier in this thread? Can't find any love interest of Superman by that name.

[Alpha]

Random question: Who is the Ruby mentioned earlier in this thread? Can't find any love interest of Superman by that name.

https://dc.fandom.com/wiki/Ruby_Carson_(New_Earth)

Never heard of her before

[Prime]

Man Clark has been around lol

[witchboy]

In terms of Earth-Two Superman it's a bit tricky. The link says "The Golden Age Superman is shown to only have eyes for Lois Lane. He played the goofy, clumsy nerd as her co-worker Clark Kent, while she swooned at Superman."

The problem here is that Earth-Two Superman is a made-up version of the Man of Steel based on cherry-picked bits of continuity from the 1930s and 1940s. If we talk about the original Superman of Siegel & Shuster, 1938 - 1947, that's a different thing.

It's important to make this point, because for Earth-Two Superman, the above quote could very well be true. It could be that Lois Lane was the only important romantic interest in his life. Afterall, he was shown to marry her in the late 1940s and stay with her until her death.

On the other hand, if we're talking about the original Superman from the '30s and '40s, while Lois was the most important love interest, there were other women that Clark/Superman was involved with. The only question might be whether he was as interested in them as they were in him.

Women tend to go mad for the Man of Tomorrow, and some even are attracted to Clark Kent, yet Supes is pretty cool toward most women, even Lois. As Clark, he might have acted like he was thirsty for Miss Lane, but that was probably Superman overplaying his part as the overly infatuated Kent.

That is an important distinction. Most people do treat the Earth 2 Superman as being the same as the actual Golden Age Superman, when they're not the same.
I have read the Golden Age Omnibuses, and sometimes Superman/Clark is genuinely crazy about Lois and caught up in his own tangle of dual identities so that he can't make it work with her in either identity. It's a fun dynamic and I prefer it to him being more aloof and indecisive with her, which became more of a thing in the Silver Age.