Wheatley in the Portal 2 fic Test Of Humanity after becoming a cyborg (GLaDOS implanted his "brain" into a human body For Science!). Tall, nerdy-looking, clumsy, noticeably chubby, yet friendly and well-meaning. Even Chell admits she finds his awkward nature to be endearing and it's part of the reason she falls in love with him.
Luna: This is great! We cannot wait! Astronomical Observations! Telescope Calibration! And Trivia Pursuit! This should be a detonation! Is that the right wording? This should be a detonation? Celestia: íThis should be a blastí is more commonly used.
Caramel of Assumptions becomes this trope whenever an attractive girl talks to him directly, constantly stuttering and flubbing his lines. Ironically, his main love interest grows fond of him since he doesn't act differently around her, though he does regress back into this after a few teases from her.
District One Career and eventual victorObsidian who, despite his initial displays of coolness, can be downright awkward, especially when it comes to his Love Interest—Vale. See also: his rehearsal of how he would propose an alliance with Vale, as well as plenty of the not exactly cool things he says once he and Vale actually do team up.
Tojo in The Lion King Adventures. He's a squeaky, geeky nerd. However, he's absolutely adorable. It's impossible not to love him.