Contestants were asked to submit their solutions in the comments below the pinup. Although I got a lot of great entries, nobody's solution quite struck me as the PERFECT answer. So, I've decided to mix and match.
One solution, by Dave, began with the phrase, "Chip Slatherton, Daily Wombat!", which I quite enjoy. He also named the heroine Chickzilla, which I think fits her look. My idea, based on that, is that she is hotel heiress Chica Ramada, and that she's been dubbed Chickzilla by the tabloids.
Several people posited gags on the raunchier side. Which is understandable, considering Chickzilla's short dress and Chip's angle on things. I think there could be a solution which addresses this issue, without getting too crass. How about: "Chip Slatherton, Daily Wombat! Miss Ramada, would you mind keeping your legs together for just two seconds, so I can get a decent photo?"
On the milder side, Kevin came up with:
Bear: Any chance a guy like me has a shot
with a dame like you?
Bear: What say we take a chance and see what
Ha! Nice puns, Kev. I thoroughly enjoyed this answer. But since I've fallen in love with the idea of Chip's being a wombat, I don't think I'll go with the bear joke.
Joelle bided her time for a couple weeks, then finally chimed in with an ambitious piece of dialogue, including a complete story arc and the inner thoughts of both characters. A+ for enthusiasm alone, Joelle! And within her solution was the following exchange:
He: How do you stay in such great shape?!
She: By walking fast and kicking little jerks
like you to the curb.
I really like that, because one can plainly see her muscular legs and the curb in the picture. And I like the phrase "kicked to the curb," and judging by Chip's position between Chickzilla and the street, he's clearly in danger of being LITERALLY kicked to the curb.
The rest of Joelle's answer, like Kevin's, expresses the hopeful notion that the two may strike up a relationship, which warms my heart. But for brevity's sake, I think we'd better cut it.
So, in conclusion, by combining my favorite attributes from the answers of both Dave and Joelle, here is the winning solution:
Chip: Chip Slatherton, Daily Wombat! Miss
Ramada, how do you stay in such great
Chickzilla: By walking fast and kicking
little jerks like you to the curb.
Prizes will be awarded to both winners.