The Simpsons: All Of Bart's Love Interests, Ranked Worst To Best

Greta Wolfcastle is, as the name suggests, Rainier Wolfcastle’s daughter, although she’s only in the show for a fleeting appearance. Voiced by Reese Witherspoon, Greta is a decent character with some funny scenes, but overall the rushed way the episode concludes just keeps her out of the top five.

She’s sweet without needing Bart to change, and she’s got enough of a playful side that they seem like a great match. Bart, however, sees them as just friends, until Lisa points out how oblivious he’s being. Things fall apart from here on out as Bart, despite liking Greta, thinking she’s pretty and having dated girls before, breaks up with her.

There’s no real justification given for this, and even less for the fact she gets together with Milhouse shortly after. She was constantly annoyed by Milhouse when they were together, so why she’d snag him on the rebound is never really explained.

They do at least get some good scenes out of Rainier’s involvement, and Greta and Bart could’ve been a good pair if a few things had gone differently. At least she brought him and Milhouse a little closer.