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A chronological list of boys that Lisa has shown romantic interest in:

Confirmed

  1. S04E15/S09E17: Ralph Wiggum ("I Love Lisa", no canonical "Lisa the Simpson")
  2. S06E19: Hugh Parkfield ("Lisa's Wedding")
  3. S07E20: Langdon Alger ("Bart on the Road")
  4. S08E07/S19E12/VABF02: Nelson Muntz ("Lisa's Date with Density", non-canonical "Love, Springfieldian Style" and "Barthood")
  5. S12E04: Jesse Grass ("Lisa the Tree Hugger")
  6. S12E18: Thelonious ("Trilogy of Error")
  7. S14E18: Luke Stetson ("Dude, Where's My Ranch?")
  8. S14E12 and others: Milhouse Van Houten (non-canonical "I'm Spelling as Fast as I Can" and others)
  9. The Simpsons Movie: Colin (The Simpsons Movie)
  10. S21E12: Milhoose ("Boy Meets Curl")
  11. S22E04: Edmund ("Treehouse of Horror XXI")
  12. S23E13: Nick ("The Daughter Also Rises")
  13. S25E17: Lucas Bortner ("Luca$")
  14. S27E17: Jack Deforest ("The Burns Cage")
  15. S28E12: Blake Black ("The Great Phatsby")
  16. S29E??: Brendan ("Haw-Haw Land")
  17. Simpsons Comics #33: Martin Prince (Rhymes and Misdemeanors)
  18. Simpsons Comics #97: Q-Bert Spuckler (Feud, Glorious Feud!)