stile86 is correct! Although this panel comes from an imaginary story from Lois Lane #89, it makes perfect sense for Superman to lend his flight ring to the then powerless Diana during her phase as the "Mod" Wonder Woman...
"I am the LEGION--you colossal Jerk!"--Garth Ranzz LEGION #63
Excellent question. I don't remember this and hadn't thought of her Mod phase but knew that her ability to fly or not without her invisible plane has varied depending on the writer so thought that might be it.
Which three legionnaires tried to help Jimmy Olsen to win over Lucy Lane?
In Superman's Pal Jimmy Olsen #76 Jimmy is having a date with Lucy Lane at his apartment which isn't going very well when the Legionnaires appear in a Time Bubble saying they need Jimmy to come to the future to help them. Reluctantly he leaves Lucy sitting in front of that standard of all american apartments, a timeviewer focused on the 30th Century. In the future Jimmy helps on three missions, each time helping or saving one of Lu, Imra or Ayla who each give him big hugs and kisses at the end. Finally they start fighting amongst themselves for who gets him as a boyfriend. Jimmy defuses the situation by returning to the 20th Century, after which we see the three laughing about their antics and pretend missions which were all designed to make Lucy jealous (because according to comics that was the way to win a girl or a guy in the 50/60s - never actually seemed to work). Unfortunately Lucy fell asleep just after Jimmy left and thinks he is making the whole "jealous girl legionnaires" thing up and storms out.
There is a follow-up in issue #100 when Jimmy actually marries Lucy. Before the wedding he takes a time bubble (which he has locked away in a room of his apartment) to the future to give the three girls the bad news. They remember their previous act and don't have the heart to disillusion him so pretend to be heartbroken. Jimmy leaves thinking "Just three victims of the fatal Olsen charm! Too bad!" (The wedding goes ahead but thanks to hijinx by Miss Gzptlsnz, whenever they kiss Superman turns into a super-mole. This is silved by another of Jimmy's alien girlfriends who threatens to turn everyone he kisses to stone. After she is defeated another turns up and Lucy finally decides that there will always be another threatening girlfriend and for the sale of their friends they must get the marriage anulled to which Jimmy agrees. A judge agrees to do so since the marriage "was in name only" (no consumation I guess) and that they agree to be friends. Such wonderful silver age craziness.
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