"Once Upon a Time…" The Top 10 Love Stories of Our Generation’s Pop Culture

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by Alexandra Ley


These are the love stories we knew growing up—of the couples we’ve rooted for and wish we could write to for relationship advice. Most importantly, they’re ours and characterize romance for our generation. Sure, the entire world delights in the romances of Pride and Prejudice and Casablanca, but these couples stand out specifically for our generation’s collective memory and taught us how to date, how to NOT date, and yes, how to use the phrase “on a break.”
Here are the love stories of the last twenty years that have captured our generation’s hearts and imaginations.
Note: In cases where the popular version of a story differed from source material, the following material was based off the popular version our generation is most familiar with.
10. Sabrina Spellman and Harvey Kinkle (Sabrina The Teenage Witch- 1971 comic series, 1996-2003 TV series)
“What happened to saving the world?” “I did. You are my world”


How they met: Sabrina started a new high school on her sixteenth birthday and saw Harvey through a window. They turned out to be in the same biology class, but when Harvey tried to ask Sabrina to be his lab partner, Libby asked him to pair off with her instead.
First date: Unknown.
First kiss: In Harvey’s car in Sabrina’s driveway, after an awkward date where Sabrina refuses to kiss him. Her aunts told her that because she is part witch, if she kisses him, he might turn into a frog. Sure enough, this happens.
Obstacles: Sabrina’s inability to explain weird actions and occurrences because she cannot tell Harvey she is a witch; Libby’s constant attempts to sabotage their relationship and seduce Harvey; Harvey’s aversion to Sabrina’s supernatural powers; Sabrina’s engagement to Aaron
Break-ups/Make-ups: Harvey breaks up with Sabrina when he finds out she is a witch.
Where they left off: Sabrina leaves Aaron at the altar and finds Harvey outside the church. They ride off on a motorcycle together.
9.  Kathleen Kelly and Joe Fox (You’ve Got Mail- 1998 film)
“I wanted it to be you. I wanted it to be you so badly.”


How they met: In a chat room online. Later, they meet in person at Kathleen’s bookstore, where Joe takes his younger relatives for “storytime.”
First kiss: In Riverside Park, where Kathleen has an online meet-up, and it turns out to be Joe and his dog Brinkley.
First date: Unofficially at a coffee shop where Kathleen waits with a rose and a book, and Joe “interrupts” without telling her he is her online contact.
Obstacles: Competing businesses (Joe’s corporation FOX books shuts down Kathleen’s independent children’s bookstore); the media war Kathleen starts in retaliation for FOX books moving in; Kathleen’s lack of knowledge of Joe’s online alias; Kathleen’s relationship with Frank; Joe’s relationship with Patricia; their tendency to disagree on everything
Where they left off: Kathleen told her online pen-pal that she would meet him in Riverside Park and is overjoyed to see Joe waiting for her.
8. Belle and the Beast (Beauty and the Beast- 1740 fairy tale, 1991 Disney animated feature)
“There may be something there that wasn’t there before.”


How they met: Belle’s father Maurice got lost in a forest and found himself at the Beast’s castle. The Beast took him prisoner and Belle went to the castle to retrieve him and exchanges herself for her father’s freedom.
First kiss: Belle had just saved the Beast’s life by telling him she loved him as the final rose petal (signifying the time limit for the Beast’s curse to find someone who loved him despite his outer appearance) dropped. The curse was broken and he was turned into a handsome Prince. Belle kissed him when she saw in his eyes the same creature she had grown to love.
First date: Dinner together in the castle.
Obstacles: The Beast’s anger at the world; The Beast did not want to treat Belle kindly when he first took her prisoner; Belle’s anger at the Beast for imprisoning her father; Belle’s disobedience of his orders and going to the West Wing of the castle; both of them having stubborn tendencies; Belle leaving the castle to take care of her father
Break-ups/Make-ups: None known, but the Beast did release Belle and resigned himself to never seeing her again. When Belle found out that the mob was attacking the castle, she returned to save him.
Where they left off: Belle and the Prince lived happily ever after.
7. Buttercup and Wesley (The Princess Bride- 1973 novel, 1987 film)
“Death cannot stop true love. All it can do is delay it for awhile.”


How they met: Wesley worked on a farm in Florin for Buttercup’s family and she liked to boss him around, have him respond, “as you wish.”
First kiss: Occurred on the farm, shortly after Buttercup realized she loved Wesley.
Obstacles: Buttercup heard that Wesley was killed by pirates; Prince Humperdinck chose her to be his bride so that she could die and he could blame Florin’s rival country Guilder; she was kidnapped by a gang hired by Humperdinck’s advisor Count Rugen; lightning sand; fire-spurts; Rodents of Unusual Size; Rugen’s life-sucking machine almost killed Wesley; Buttercup believed Wesley was dead and tried to kill herself when she believed she was legally married to Humperdinck
Break-ups/Make-ups: Buttercup believed Wesley was dead, but never stopped loving him. They were reunited when Wesley tried to rescue her from Vezzini, Inigo, and Fezzig.
Where they left off: The two rode away on horses from the castle in Florin and shared the most passionate kiss in world history.
6.  Rose DeWitt Bukater and Jack Dawson (Titanic- 1997 film)
“When this ship docks, I’m getting off with you.”


“This is crazy.”
“I know. It doesn’t make any sense. That’s why I trust it.”


How they met: Rose was hanging off the stern of the ship, contemplating suicide, when Jack walked by and yelled to stop her. Rose was surprised and lost her grip, and Jack helped her back up onto the deck.
First date: Rose defies her mother and fiancé to meet Jack on the bow of the ship, where Jack holds her so that she can “fly.”
First kiss: While “flying” at the front of the ship at sundown (with Celine Dion warbling in the background, of course).
Obstacles: Differing social classes made it hard for them to be together on the ship, and Rose’s mother Ruth disapproved of Jack; Rose’s fiancé Cal framed Jack for stealing; the ship they were on sunk; Jack froze to death; Rose’s marriage
Break-ups/Make-ups: Although not exactly a break-up, Rose was appalled to find out that Jack had “borrowed’ another man’s jacket and stopped sticking up for him in front of her family. During the ship’s sinking, Jack was handcuffed to a desk in a flooding room, and Rose helps set him free.
Where they left off: Jack froze to death after the ship’s sinking, but Rose took his name and started a new life away from her family when the Carpathia docked. She eventually married and had children, but never forgot her voyage on the Titanic or her love for Jack.
5.  Noah Calhoun and Allie Hamilton (The Notebook- 1996 novel, 2004 film)
“It’s going to be really hard; we’re gonna have to work at this everyday, but I want to do that because I want you. I want all of you, forever, everyday. You and me…everyday.”


How they met: Noah fell in love with Allie when he saw her at a carnival. She was in a ferris wheel cart with another boy when he jumped up onto the bar of the cart and threatened to let go unless she went on a date with him.
First kiss: Unknown.
First date: Noah’s friend sets up a blind double date to see Lil’ Abner with his girlfriend and Allie (who had previously made it clear to Noah that she did not want to make good on her promise). Noah and Allie walk home, stopping to talk, lie down on the pavement, and dance in an empty street.
Obstacles: Allie’s structured life and strict family; different socioeconomic backgrounds; the Hamilton’s disapproval of Noah; living in different places; a constant lack of communication with each other while apart; Noah’s enlistment; Allie’s engagement to Lon; Noah’s relationship with Martha; Noah’s heart problems and Allie’s dementia later in life
Break-ups/Make-ups: Allie breaks up with Noah because he mentions breaking up at the end of the summer when Allie leaves Seabrook, because he does not want her to feel tied to him when does not think his life is right for her. Allie finds Noah and her old summer home later through a picture in the paper and returns to Seabrook.
Where they left off: Noah gets Allie to recognize him despite her dementia, and the two died side-by-side in a nursing home, still in love with each other.

4.  Ross Gellar and Rachel Greene (FRIENDS- 1994-2004 TV series)
“Just so you know…with us…it’s never off the table.”


How they met: As children growing up on Long Island, Rachel was best friends with Ross’s sister Monica. Specific moment is unknown, but Ross knew he wanted to date Rachel when he was in ninth grade.
First kiss: Ross and Rachel have a fight in Central Perk after Ross finds out Rachel had feelings for him, because Ross does not want to screw up his relationship with Julie. Ross storms out into the rain and Rachel closes the door, turns off the lights, and starts to cry. She turns to continue cleaning up and sees Ross standing in the doorway. She has trouble unlocking the door until Ross tells her which lock to try, and she opens the door, letting in the rain and Ross.
First date: A movie, and a lot of awkward kissing, because Rachel cannot stop laughing about the fact that Ross is kissing her.
Obstacles: Rachel’s relationships with Barry, Paulo, Joshua, Danny, Tag, and Joey; Rachel’s engagements to Barry and Joey; Ross’ relationships with Julie, Bonnie, Rachel’s sister Jill, Elizabeth, Emily, and Mona; Ross’ marriage to Emily; Ross’ inability to communicate; Rachel’s inability to take a hint; the “I Hate Rachel Greene” Club Ross started in high school; a pro/con list Ross makes between Rachel and Julie; Rachel’s father disapproving of Ross; Ross’ intense jealousy of Rachel’s boss Mark; Rachel’s devotion to her job at Bloomingdale’s; Ross sleeping with Chloe after Rachel suggested they “take a break;” Emily asking her newly-wed husband Ross to never see Rachel again; divorcing after a drunk Vegas wedding to each other; arguing about how to raise their child Emma; a tempting job offer for Rachel in Paris
Break-ups/Make-ups: Rachel was insulted by the pro/con list Ross made between her and Julie and decided she did not want to be with Ross. She made up with him when they watched Monica and Rachel’s prom video, which revealed the fact that Ross got dressed up to take her to her senior prom when her date cancelled. The two had a bumpy relationship, and fought on their first anniversary about Ross’ jealousy and Rachel’s workaholic tendencies. Rachel suggested that the two “take a break,” and in response, Ross gets drunk at a club and sleeps with Chloe. Rachel finds out the following day and dumps him for good. The two had a number of hook-ups, multiple one-night stands, a marriage, a divorce, and a baby over the next 7 years, but did not officially begin dating again until Rachel left her plane to Paris right before it took off so that she could tell Ross she loved him.
Where they left off: Rachel stayed in New York instead of moving to Paris, and Rachel and Ross began dating and raising Emma together.
3.  Edward Cullen and Bella Swan (Twilight- 2005-2008 book series and 2008-2012 film series)
“If I could dream, I would dream about you.”


First kiss: After spending some time at a meadow by Forks High and talking about Edward’s life as a vampire, they walked back to Bella’s truck and Edward asked Bella to try something.
First date: A few hours in a forest and a meadow by Forks High.
Obstacles: Bella’s mortality; Edward’s almost-uncontrollable urge to suck Bella’s blood every time she gets near him; Bella’s family friend Jacob Black, who turns out to be a werewolf who is also in love with Bella; James, a vampire who tries to hunt Bella; Edward’s reluctance to change Bella into a vampire; Edward’s desire for Bella to have a normal life; the Cullen family’s rivalry with the Blacks, who are friends with Bella; the treaty that states that the families will fight if the Cullens bite a human; Edward’s desire for the Volturi (basically the members of a very strict vampire government) to kill him when he thinks Bella is dead; Victoria and Laurent, vampires who want to avenge James’ death; Jacob’s wolfpack who want to kill Bella when she becomes pregnant with a half-vampire baby; the Volturi who do not want Bella to know about vampire secrets and later mistakenly believe she has turned a child into a vampire
Break-ups/Make-ups: After Edward’s foster brother Jasper tried to suck Bella’s blood at her eighteenth birthday party, Edward decided that his lifestyle was too dangerous for her and left Washington. Edward’s clairvoyant foster sister Alice had a vision of Bella cliff-diving, but mistakenly thought Bella has committed suicide, which is what she told Edward. Bella and Alice flew to Italy to stop Edward from revealing his secret to the world, and Bella and Edward reunited.
Where they left off: After all the trouble that they have had, Edward and Bella are ready to live happily with their crossbreed daughter Renesmee and her soul mate Jacob.
2.  Hermione Granger and Ron Weasley (Harry Potter- 1997-2007 book series and 2001-2011 film series)
“It’s now or never, isn’t it?”


How they met: On the Hogwarts Express, first year of Hogwarts. Hermione was looking for Neville’s toad in Harry and Ron’s compartment. She mocked Ron for not knowing real spells and Ron was annoyed at her for trying to be right at everything. She left to keep looking for the toad and Ron hoped out loud to Harry that he would be in a different house than she would be.
First kiss: During the Final Battle at Hogwarts, in the Room of Requirement. Ron voiced concern to Harry and Hermione about the house elves working in the school kitchens and wanted to get them out of the battle. Hermione, who had been very active in fighting for the rights of house elves for four years, kissed him, which Ron reciprocated enthusiastically.
First date: Unknown.
Obstacles: Hermione’s tendency to be an annoying know-it-all; Ron’s lack of tact; Hermione’s relationship with Victor Krum; Ron’s relationship with Lavender Brown; Death Eaters; a Wizarding War; Voldemort’s determination to eliminate Muggle-borns (like Hermione), blood-traitors (like Ron) and allies of Harry Potter (both of them) from the Wizarding World.
Break-ups/Make-ups: None known.
Where they left off: Ron and Hermione got married, both worked at the Ministry of Magic, and had two children named Rose and Hugo.

1.  Topanga Lawrence-Matthews and Cory Matthews (Boy Meets World- 1993-2000 TV series)
“The only thing that ever made sense to me was you, and how I felt about you. That’s all I’ve ever known, and that’s enough, enough for me, for the rest of my life.”


How they met: On the playground, as toddlers. Topanga helped give him the courage to jump off the monkey bars when he was scared.
First kiss: In the school hallway in sixth grade. Cory was handcuffed to a locker after yelling to a bunch of students to sign a petition. He jokingly mentioned that Topanga should kiss him for his bravery, and she took him seriously. When Cory could not free himself from the handcuffs, he told her they shouldn’t kiss because they weren’t married. Topanga thought for a minute and agreed that she would need to know and like the person, then pinned Cory to the locker and kissed him.
First date: Unknown.
Obstacles: Cory’s eighth-grade awkwardness with everyone of the female sex; thinking they’d be better off as friends; Topanga’s family moving to Pittsburgh right before ninth grade; Cory kissing another girl on a skiing trip in high school; Topanga getting accepted to Yale when Cory was going to Pennbrook College.
Break-ups/Make-Ups: Topanga broke up with Cory briefly when he told her “I love you” and she freaked out. They reconciled when Cory climbed through Topanga’s bedroom window and they talked about their relationship. Later that year, they decide to try being friends, but Cory follows her to Disney World a few months later to show Topanga he wants her back. While on a skiing trip, Cory kisses another girl and lies about it, and when Topanga finds out, they break up again. They reconcile in time for prom, where they are crowned King and Queen.
Where they left off: Moved to New York with their friends from high school and college so that Topanga could work at a law firm. 


All photos courtesy of www.fanpop.com


Alexandra is a sophomore at Barnard College and a staff writer for The Nine Ways of Knowing.
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2 thoughts on “"Once Upon a Time…" The Top 10 Love Stories of Our Generation’s Pop Culture

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