Skylar Feldman (canonically Skyler but fandom spelling is so ingrained that should we wade no more, returning were as tedious as go o'er) is a student of Lawndale High, seen in "Pinch Sitter". Skylar is wealthy — his family has a boat — and seems to be stuck up and impressed with himself. He considers himself a good match for Quinn because "I know that plenty of guys want to go out with you, and plenty of girls want to go out with me."
He's the date that forces Quinn to find a substitute babysitter for the Guptys. He takes her to Chez Pierre and suggests that as the two most datable students in school, they should go steady. Quinn accepts, but has no intention of changing her dating habits and plans to break up with Skylar in the fall because his parents' boat won't be of as much use then as Taylor's parents' ski lodge. Skylar is not happy to find this out, nor that she was actively planning on dating his best friend Eric simultaneously with him.
He does not have another speaking role, although some people theorize he is Quinn's second date (other than Corey) in "Daria Dance Party".
In a "Love is a Way Too Many Splendored Thing", Quinn says: "His family owns a boat so he's the perfect match for me…at least until Labor Day."
Skylar in Fanfic
Because of his perceived smarm and egotism, Skylar is often used as a villain in Daria fanfic—most notably in "Sins of the Past" by Martin J. Pollard, where he rapes and beats Quinn to punish her for using him. The Angst Guy went against the grain in "And When Your Heart Begins to Bleed", making Skylar a sympathetic character who Quinn is considering going steady with for real. thatLONERchick went further in "A Question" by having Skylar break the fourth wall and question the rumors of being being either insane or a psycho killer.
In The Excellent S's Lawndale Fighting Championship, Skylar appears occasionally as a wrestler in battle royals and multi-person tag matches. Skylar also appears in Shiva's Sexy Daria as a love interest for Daria who wants to join Drama Club.