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He is a British student who becomes engaged to Lisa 15 years in the future, but after he insulted her family, she breaks their engagement off.
In the future, 23 year old Lisa becomes annoyed by Hugh and at first, the two quarrel over a book in the library, but the pair eventually fall madly in love.
The two discover they have a lot in common and Hugh invites Lisa to come back to his home in England so she can meet his parents.
Hugh asks Lisa to marry him and she immediately accepts. Lisa and Hugh travel to Springfield where Lisa is worried that her family will embarrass her and things get off to a bad start when Bart and Homer accidentally set the British Union Jack flag on fire, which they put out by throwing compost onto it.
At dinner, Lisa plans on going for a wedding dress fitting and Homer decides to take Hugh out on the town to Moe's Tavern. While there, Homer presents Hugh with a tacky pair of cuff links (a bride and groom pig) that all Simpsons men have worn on their wedding day, asking him to continue the tradition; Hugh reluctantly agrees to wear them during the wedding.
Later that night, Lisa apologizes profusely for the behavior of her family and although Hugh says it was nothing, he stays up thinking. On the day of the wedding, Homer talks with Lisa and she discovers that Hugh did not wear Homer's cuff links.
She finds Hugh and asks him to wear them. He agrees, but lets slip that after the wedding he plans for them to return to England and never see her family again. Lisa is outraged and calls off the wedding.
Back in the present once more, the fortune teller says that Hugh went back to England and never saw Lisa again and that there was nothing Lisa could do to prevent it - although she should "try to look surprised".
Lisa questions the fortune teller about her "true love" and the fortune teller reveals that although Lisa will have a true love, she "specializes in foretelling relationships where you get jerked around."
Lisa leaves the booth and finds her father, who brags about his day at the fair and Lisa listens raptly as the two walk off, undoubtedly grateful to Homer after she saw what his future self had done for her.
- Mandy Patinkin as Hugh is considered one of the best Simpsons guest spots by Chris Turner in his book Planet Simpson, who says that many of the best Simpsons guest stars have been lesser known celebrities.
- Hugh Parkfield is a parody of English actor Hugh Grant.
- The scene where Lisa and Hugh fall in love after arguing over a book is similar to Ali McGraw and Ryan O'Neal in Love Story.
- According to the wedding invite, Hugh's full name is Hugh St. John Alastair Parkfield