The phrase "lovable loser" refers to a person who is not very successful or lucky, but they are still well-liked and people feel affection for them. Full definition
So you hear that Johnson and his TV castmate Damon Wayans Jr. are starring in «Let's Be Cops» as lovable losers mistaken for LAPD officers, and you're hopeful. (bostonglobe.com)
Year: 2006 Lamer Alternate Title: Reefers Can Still Be Deadly Plot: A group of lovable losers buys a bong that comes with an unexpected feature: a voodoo curse that transports those who use it to the «Bong World,» where undead strippers give lethal lap dances. (thoughtco.com)
Despite Boden and Fleck's narrative embellishments, Mississippi Grind is still very much a movie about lovable losers, leaning hard on the charisma of its two stars. (film.avclub.com)