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Answer for the clue "Silly in an endearing way ", 5 letters:
dippy

Alternative clues for the word dippy

Word definitions for dippy in dictionaries

Douglas Harper's Etymology Dictionary Word definitions in Douglas Harper's Etymology Dictionary
"mad, insane, crazy," 1903, perhaps from dip + -y (2), but the exact signification is unclear. Another theory connects it with dipsomania .

Wiktionary Word definitions in Wiktionary
a. Lacking common sense

Wikipedia Word definitions in Wikipedia
Dippy is a public sculpture of a Diplodocus dinosaur on the grounds of the Carnegie Institute and Library complex in the Oakland neighborhood of Pittsburgh , Pennsylvania . The life-size fiberglass model depicts Diplodocus carnegii , a species named for ...

Usage examples of dippy.

But this was the time of day when Dippy liked specially to prance and jump and skurry after dusky, shadowy, flitting things, so before Marian could pounce upon him, he was off and away like a streak and could not be found.

Rootabaga Stories and More Rootabaga Stories are best suited as read-aloud books for very young readers, who will probably have more patience for characters with names like Dippy the Wisp, Rags Habakuk, Shush Shush, Snoo Foo, Bixie Bimber, and Wingtip the Spick than their older siblings will.

Of all the horrors of the civilized world, I had decided clam, oyster and bleu cheese dips were the worst, and of the worst, Stella Soles's dips were the dippiest.