The Simpsons: All Of Bart's Love Interests, Ranked Worst To Best
8. Jenny
Jenny is the sweetest girl on this list, and easily the worst match for Bart of the lot. However, since she’s part of a decent storyline and the Simpson lad shows a bit of growth, there’s enough here to haul her up to just under halfway.
Anne Hathaway lends her voice to Jenny, a nice Christian girl who volunteers at the Retirement Castle. Instantly smitten, Bart begins acting nice in order to get her attention, and the pair begin dating. Bart does appear to change a little, although he quickly snaps back to his usual ways.
The downside of her is that the ‘Bart pretending to be good’ is just a rehashed version of a much earlier plot, done with more intelligence. As a result, Jenny doesn’t feel especially original and falls way short of the first girl to play out this storyline.
Not only that, her appearance and general disposition aren’t too dissimilar to Samantha Stankey, Milhouse’s ex-girlfriend. Further to this, Milhouse sabotages their relationship just as Bart sabotaged Milhouse and Samantha’s. A nice enough one-off character but she just seems like a collection of older love interest ideas combined into something new.