From: Superman #142, Action Comics #272 , and Superboy #86 (January 1961)
In "Lois Lane's Secret Helper" (Superman #142), Krypto gets wind of Lois Lane's despair that Superman will never marry her, and he decides to help things along and play Cupid. But first, to observe how humans choose mates:
Ah yes, the power of the serenade. It should not be undervalued. So Krypto rounds up some birds and...
Oh crap! Superman's gonna pull a move! Those birds can really sing---ahhhhh no!!! Who played an Interrupt!?
Cat blocked! Well, there's more than one way to skin a cat. Krypto next observes that people left on a deserted island together quickly turn into Adam & Eve. Coincidentally, Clark and Lois have borrowed Perry's speedboat while the boss man fishes. What if they were shipwrecked?
Additional problem: Lois wants Superman, not wussy Clark Kent, so if Krypto is going to make her fall for Clark, he needs to address this. So he starts an earthquake on the island, when Lois actually starts to seem willing, and...
Kryptonite under the sand?! Krypto can't seem to catch a break (except for the coincidences that keep piling up at the start of his attempts). A rescue helicopter is soon on the scene; it's a bust. Next, Krypto notices that peer pressure is an important element in making people propose. Somewhere in Europe, he sees a guy ask his girlfriend in marriage when he sees another couple get hitched. Well okay then. It must be true. As it so happens, Lois has just inherited a female dog from the Daily Planet lost and found, so Krypto brings her a ton of bones and makes "Beauty" fall in love with him. When Superman sees this, he has a moment of weakness.
Except all those bones make a bunch of dogs escape from the pound truck and interrupt the moment. Oh damn. Well, one last try:
Superman's wink makes me think he engineered all those "fails" somehow, but since there's no explanation, we'll just have to let it go. If you're taking notes, your dog leaving you because you're a bachelor will not make you want to get any more married than before. Sorry Lois!
MEANWHILE...In the same issue, Krypto is used as a messenger service for Super-trolling in "Flame-Dragon from Krypton".
He lifts a safe from the inside to simulate telekinesis in Action Comics #272's "Superman's Rival, Mental Man!".
And is grabbed by Luthor's animated kryptonite giant in Superboy #86's "The Army of Living Kryptonite Men!"
A busy month for the Dog of Steel!
Comments
That's a lovely Supergirl, unusual hair. Is it Al Plastino's work?
As an aside, I loved the days when heroic meant "platonic even with Lois", constantly foiling her romantic notions. Even here he's too cool to propose.
Sexuality was an alien concept to the comics. Just think how many folks with "alternative tastes" could read the comics and not feel excluded because what a character may or may not do in the dark was irrelevant (except of course for Batman).... besides, grossing kids out was considered WAY uncool.
Getting all "adult" kinda spoils the fun of comics, and if they ain't fun....
I was born about three decades too late.