The Simpsons: All Of Bart's Love Interests, Ranked Worst To Best
7. Shauna Chalmers
Shauna Chalmers is one of the best characters to have been introduced pre Season 10 (first appearing in Season 20), but when it comes to Bart’s love interests she’s middle of the pack. In fairness, she’s much more than just an add on to Bart, which was always going to hurt her in a ranking like this.
She’s been a love interest for Jimbo as much as she has for Bart, with Bart and Lisa even being babysat by the couple in a recent Season 30 episode. As well as Bart and Jimbo, she’s been seen as the Squeaky Voiced Teen’s girlfriend too, managing to add some depth and offer new gags to character who’d gone a little stale.
However, while her flexibility helps make her more memorable and funny, it also puts her relationship with Bart into slightly icky territory. Her age is never clearly established, but Bart is definitely 10 and the Squeaky Voiced Teen is probably 16 at the youngest, given the jobs he works.
Therefore, her kind of dating Bart (and even flashing him her bra) feels a little weird given she’s also 16 at the youngest. A welcome addition to Springfield, but only a so-so Bart love interest.