A description accorded to people whose behaviour is by normal standards considered weird or unusual, but is nevertheless deemed to be rather cute. The etymology of this word derives from encounters between one biracial bombshell and one tall, lanky American, the latter for which the term awkwardly endearing was coined for.
When a boy offers to buy a girl a cup of coffee out of gratitude for her having sent him notes. Although sweet the offer, in saying, "so you can snuggle up a little longer in bed in the morning", it is more than a tad bit weird. In other words, it is awkwardly endearing.
by Voldemort III March 10, 2008
What one becomes after having a crush on an awkwardly endearing individual. Like an STI the curse of being awkwardly endearing can be passed on through even minor contact.
When that individual who at one time attained the ‘biracial bombshell’ status loses her ability to engage in regular social encounters without saying something odd. Examples include multiple references to: Manchester City, graphic novels, the library, War and Peace, and timbits. This awkwardly endearing master status cannot be used to account for the recent Distal Radius fracture suffered by this individual. Any such bone-breaking must be attributed to a previously existing clumsiness condition.
by Voldemort IV May 7, 2008