adorkable
adj. Delightful and charming in a socially awkward way.
Etymology
Examples
2008
Michael Cera walks into a room at the Four Seasons Hotel in Toronto, shrugs off his red knapsack, and shyly asks if anyone minds if he makes himself a cup of java.

"Do you mind if I make a coffee real quick?" asks the actor. "I like it with sugar and milk," he explains. "It's really, really delicious." And while he stirs with a plastic stick, the 20-year-old chats — in his halting, adorkable way — about his new film, Nick and Norah's Infinite Playlist, a light-hearted, indie version of a John Hughes coming-of-age film.
—Gayle MacDonald, “Michael Cera, the little dweeb who could,” The Globe and Mail, October 04, 2008
2008
A humorous coming-of-age drama with a quirky, sci-fi slant and a hint of romance, "Chill" centers on the attempts of Jeremy to become cool. An adorkable, articulate young man so self-conscious he keeps a list of "mortification events" detailing his social blunders, Jeremy wants to learn to dress right, talk right, act right thereby making himself over into the person Hollywood and Madison Avenue say he should be.
—Barbara Vitello, “Griffin gives teen angst the cool treatment,” Chicago Daily Herald, May 23, 2008
1999 (earliest)
Brad Pitt. He's such a *dork*. He *is!* He's so aDORKable!
—Warren Cheney, “Admin: I bow out,” soc.singles.mederated, July 26, 1999
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