Laura Powers Appearences: 9F06 - New Kid on the Block
When the Winfields move away from Springfield, the Powers move in. Bart and Lisa sneak into the house and after Bart scares Lisa away Laura comes up behind him and scares him too. Bart falls in love with Laura, so much so that he specifically requests her for a babysitter. Bart later finds out that Laura is seeing Jimbo Jones, and calls Moe claiming to be Jimbo to show Laura that he's a wimp.

Jessica Lovejoy Appearences: 2F04 - Bart's Girlfriend
Reverend Lovejoy noticing that not everyone is paying attention in his sermons gets his daughter Jessica to read them afterwards, Bart falls for her, and tries to alter his personality to get her to notice him, but fails. Bart gets scammed by Principal Skinner, Jessica notices and invites him to dinner. One Sunday, Jessica steals from the Collection Plate, but Bart is blamed. With Lisa's help he is able to clear his name, fingering Jessica in church.

Greta Wolfcastle Appearences: 2F04 - Bart's Girlfriend
When visiting a private school fare, Bart finds Greta being picked on, Bart fights them off, Greta invites him to her house, after finding out that her father is Ranier Wolfcastle. The two start a relationship, but Bart dumps her when he wants to see Skinner's bad comedy. She rebounds onto Milhouse. Bart realises that he loves her, and goes to Canada to win her back, fighting Milhouse but she dumps them both.

Darcy Appearences: JABF04 - Little Big Girl
When Bart saves the town from burning down, he is given a drivers license, which Homer uses for free rides around town for various things. Bart has enough and takes the car to North Haverbrook where he meets Darcy. Darcy believes that because he can drive, Bart is older then he really is. The two go out and eventually, Darcy asks to marry him scaring Bart. Bart comes clean that he's only 10, and Darcy says that she wants to marry him because she's pregnant, also scaring Bart. The two find out that the marraige laws in Utah are looser and the two head out there, with both leaving messages to their parents, though only Homer and Marge know that Darcy is pregnant. All four head to Utah to stop the wedding.

Jenny Appearences: LABF07 - The Good, The Sad and The Drugly
While visiting Grampa, Bart met Jenny who was giving cookies to the old folks, which got Grampa excited. Bart asks her on a picnic where he purposely acts good to be able to stay with her. Milhouse finds out that he's seeing someone and becomes upset that Bart broke his promise. Milhouse contstantly follows them around to break them up, and Bart is forced to come clean with her. When he does, Jenny dumps him.

Nikki McKenna Appearences: MABF07 - Stealing First Base
While Mrs. Krabappel is away, the two fourth grade classes are forced to merge, so the students in Bart's class are forced to share desks with the other classes. Bart gets the last seat which is Nikki's. Nikki likes to intentionally confuse Bart by alternatively hating and loving him. When he kisses her, her parents are none too thrilled forcing the school to indtroduce a no-touch policy. It's inforced so heavily that Skinner would prefer that Bart died when he fell off the roof of the school then have Nikki give him CPR.

Jenda Appearences: GABF12 - Future Drama
Jenda is Bart's date for his highschool prom, afterwards, the two go to Makeout point where Bart proposes to her. But she rejects his proposal under reasons of not being serious for providing for her. Lisa gives him advice that he should get a job to show her that he's serious about his future. She takes him back, but in Professor Frink's house, Bart is worried that Lisa might wreck her life by marrying Milhouse and he decides to dump Jenda in order to stop his sister from a terrible future.