Green’s Dictionary of Slang

(orig. US teen) an idiot, one lacking social qualities; usu. male, thus fem. as dweebette.

1964		Edwardsville Intelligencer (IL) 13 Nov. 7/1: Many lads who are not popular will try to do something superior in order to attract attention. [...] If this dweeb turns you off so completely, get the names of some other girls who need help with their geometry and channel them to him.
1987		Eble Campus Sl. Oct. 2: dweeb/dweeber – socially inept person.
1987		Frederick (MD) Post 25 Apr. A-3: She and her friends use words such as ‘dweeble’ and ‘ween bucket’ for someone who’s ‘stupid, a jerk, anybody you don’t like,’ she said.
1989		Kirk & Madsen After The Ball 340: What won’t work for one dweeb against ten bullies won’t work for one million dweebs against one million bullies.
1995		C. Hiaasen Stormy Weather 166: Lord, what an anal dweeb!
2001–09		Plentyoffish.com 🌐 Cute dweebette: seeks cute dweeb.
2004		C. Hiaasen Skinny Dip 93: What a hopeless dweeb.