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Bart's first infatuation was with Laura Powers, his babysitter in 'New kid on the Block' (episode 8, season 4) but, although she broke his heart, she was never his actual girlfriend and was dating Jimbo Jones. Bart's first real girlfriend was the daughter of Reverend Lovejoy, Jessica, who Bart dated in 'Bart's Girlfriend' (episode 7, season 6).

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