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Dobie falls (literally) for a kind-hearted girl whose parents have come up with unusual rules for guys who want to date her. Dobie must share his date with Chatsworth, and then Maynard, or call it quits completely.
Dobie believes Maynard has stolen a substantial amount of cash from Mr. Pomfritt, and Mr. Pomfritt and Maynard believe that Dobie has stolen it. Can the real thief be found before Dobie and Maynard's friendship is destroyed?
Mr. Pomfritt encourages Dobie with Robert Browning's line, "A man's reach should exceed his grasp." Dobie tries applying that in his quest for another new girl, even though Zelda warns him that, should he fail, he won't be able to crawl back to her anymore.