Adorkable

A combination of the words dork and adorable. An overly intellectual person who is nerdy, dorky and a bit geeky but in an adorable and endearing way that becomes desirable. It's meant to be a compliment. General examples from tv would be the character's 'Ross' from "Friends", 'Jim' from "The Office", and for obvious reasons 'Chuck'. It is Steve Jobs, Conan O'Brien, Chuck Klosterman, Malcolm Gladwell, and Rachel Maddow. John Cusack in an 80's movie. An extreme example is Woody Allen depending on how old he was when he starred in the film you are watching. The ratio of adorkability rises when said nerd/geek becomes successful in business and switches from glasses to contact lenses.