The male lead in the music video for Colbie Caillat's "Fallin' For You" (played by Bobby Moynihan) is clumsy, a touch overweight, and has all the surfing skill of a native Arizonan, but in spite (or because) of these obvious 'shortcomings', his girlfriend is clearly smitten with the big lug.
Green Day's Billie Joe Armstrong. A good chunk of his earlier songs are about puppy-love, and he's cute and dorky in video for "Holiday". The fact that he looks barely over half his age helps, too.
One of the three male Love Interests of Sugababes' music video "Push The Button". He's a dork with one of those Norwegian ski sweaters and black nerdy glasses and weird facial hair. Yet the hot blond woman with a bare midriff in a tight red top and a tight skirt is very much into him.
David Bowie's Jazzin' for Blue Jean, a 20-minute long-form video, is based around the Talky Bookends story of Vic, a lovestruck-but-clumsy man who tells a Celebrity Lie to the woman of his dreams and now has to find a way to personally introduce elegant, supercool rock star Screamin' Lord Byron to her. Bowie plays both men, and Vic doesn't get the girl in the end for all his trouble — which Bowie doesn't think is fair.