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Boy Meets World: 5 Best (& 5 Worst) Relationships

As one of the many incredibly popular coming of age sitcoms of the TGIF era of television, Boy Meets World followed a group of teenagers and young adults as they navigated life and love in Philadelphia. The series' main characters were the lovably awkward Cory Matthews, the bad boy with a heart of gold Shawn Hunter, and the flower child perfectionist Topanga Lawrence. But beyond this central trio, the series was populated with colorful and iconic characters, like Cory's brother Eric, Shawn's brother Jack, and the beloved teacher Mr. Feeny.

RELATED: 10 Casting Decisions That Hurt Boy Meets World (And 15 That Saved It)

Over the course of the series, the main and supporting characters found themselves pairing off in relationships both significant and disappointing, worth rooting for and totally worth rooting against. Regardless of whether they were intentionally romantic, many of these relationships would also define the series as a whole, standing the test of time as some of the best and worst decisions Boy Meets World ever made.

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Jack Hunter and Eric Matthews in Boy Meets World
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10 Best: Jack and Eric

Jack Hunter and Eric Matthews in Boy Meets World

"Don't know if this is the right time to say it: I love you, man." "Dude, don't even, man. I’m the one that loves you!" "Dude..." "Dude!" In terms of bros being bros, confessions of love don't get cornier - or more nineties - than that. Jack Hunter and Eric Matthews are conventional total opposites. Jack is learned and comes from a world of privilege, while Eric is adorably clueless and never really knows what he doesn't know.

They play off each other in the perfect way that the best comedic duos do, but the series has fun with their closeness on many occasions, playing up the potential of a romantic angle whenever it can. Based on how emotional and affectionate these two are with each other, we can't exactly complain.

9 Worst: Chet and Virna

Alan Matthews Amy Matthews Virna Hunter and Chet Hunter in Boy Meets World

Boy Meets World may have been about the kids at its core, but it never shied away from exploring the difficulties of adult life, too. As part of that, the series was unafraid when it came to showing marriages on the decline, and in particular, marriages that never should have happened to begin with. Perhaps the clearest example of that comes in the form of Shawn's parents, Chet and Virna Hunter.

Chet is hardly father of the year, which doesn't exactly make it easy for Virna to be mother of the year, either. But both Chet and Virna frequently abandon Shawn, in favor of running away from each other and living their own lives, leading to much conflict between the both of them, their son, and the Matthews family.

8 Best: Mr. Feeny and Dean Bolander

Dean Lila Bolander and George Feeny in Boy Meets World

For much of the series' run, Mr. George Feeny is nothing more than just the loving but stern teacher that follows Shawn, Cory, Topanga, and Eric around from school to school to school. But in the later seasons, the series reveals more of Feeny's personal life, including his romantic history and romantic future, too.

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Having been widowed after the loss of his first wife, Lilian, Feeny takes quite some time to find someone else to truly stir something inside of him. But when the series introduces Dean Lila Bolander, the Dean of Pennbrook University, everything just falls perfectly into place. It also certainly makes everything better to know that William Daniels and Bonnie Bartlett have been married for nearly 70 years in real life as well.

7 Worst: Jack and Rachel

Jack Hunter and Rachel in Boy Meets World

In the world of sitcoms, the unwritten honor code known as the "bro code" more or less reigns supreme. Nothing good can come of two best friends falling for the same girl. Boy Meets World sadly falls into this bad trope in the later years, introducing a love triangle between best friends Jack and Eric and new addition Rachel McGuire.

Rachel strings along both guys at first, despite clearly not being interested in Eric at all. But worst of all, when Jack and Rachel begin their relationship for real, they keep things a secret from Eric, which leads to him getting deeply hurt in the end. Jack and Rachel truly bring out the worst in each other - which is saying something, when Rachel is one of the series' least well-executed characters to begin with.

6 Best: Alan and Amy

While Shawn may not have had the most compassionate or successful parents in the world, given the state of Chet and Virna's unhappy marriage, Cory, Eric, and Morgan Matthews really lucked out in the parents department. Alan and Amy Matthews are far and away the series' most stable couple, unabashed in their love for and lifelong devotion to one another, no matter how much it may embarrass their children.

From the very beginning of the series, Alan and Amy are always presented as a team, and though they occasionally fight, no real conflicts last for very long. They weather any storm that comes their way, whether trouble caused by their children's misadventures, the premature birth of their youngest child, or concerns about their own parenting abilities.

5 Worst: Cory and Lauren

Cory Matthews and Lauren in Boy Meets World

Teenage relationships on television these days are often filled with plenty of scandals and cheating. But in the days of wholesome nineties sitcoms, it came as a real upsetting shock when Boy Meets World had Cory cheat on longtime love Topanga with Lauren, a girl he met at the ski lodge the John Adams Highs students were staying at.

Lauren (played by future icon Linda Cardellini) was unapologetic in her interest in Cory, keeping him up all night talking at the lodge, and eventually planting a kiss on him, and giving him a detailed letter about the extent of her feelings. While Cory never really returned the feelings the way she initiated them, he still went along with the flirtation to begin with, leaving a sour taste in many fans' mouths.

4 Best: Cory and Topanga

The series may have been called Boy Meets World, but Cory Matthews's story was also very much a story of boy meets girl and everything changes. In the earliest episodes of the series, it was almost unthinkable to imagine a future in which Cory and Topanga would ever be together. Cory was loud and judgmental, and Topanga was over the top and just plain weird. But over time, as their characters developed and became more refined, it became clear that these two were perfect for each other.

From middle school, through high school, college, and beyond, Cory and Topanga were always by each other's side and always supported each other's dreams. While they split a few times, and fought on plenty of occasions, they learned how to function as a team and loved one another no matter what came their way, eventually going on to raise a family of their own in the spinoff series Girl Meets World.

3 Worst: Shawn and Angela

Boy Meets World Shawn Angela

For most of the series, Shawn Hunter was a charming kid who girls swooned over left and right. Despite his difficult background, Shawn never had any trouble getting the girls, though it never seemed like the show would put him in a serious relationship of any kind. All of that changed, however, when the series shoehorned in the introduction of Angela Moore - a character who decidedly changed the series for the worst.

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There's no denying that Boy Meets World made great strides in terms of representation by prominently featuring a teenage interracial couple. But there's also no denying that Shawn and Angela were absolutely terrible for one another, frequently at odds, and almost never able to put each other's best interests first.

2 Best: Cory and Shawn

Cory and Topanga may have gotten their happily ever after, but if there's a real soulmate in Cory Matthews's life, it's absolutely his lifelong best friend, Shawn Hunter. From the very beginning of the series, these two always had each other's backs, no matter how difficult things got in either of their lives. They survived everything together, including issues with alcohol addiction, premature sibling births and wedding jitters.

They outlasted almost every romantic relationship either one of them had, even after a blowout fight during the leadup to Cory and Topanga's fairytale wedding. Shawn and Cory need each other more than they need anyone else in their lives, and even in Girl Meets World, Topanga knows better than to think that she'll ever be number one in her husband's life. And based on how much these two crazy kids love each other, we can't say we blame her.

1 Worst: Eric and Rachel

We've already discussed the real mistake the series made by introducing the love triangle between Jack Hunter, Eric Matthews, and Rachel McGuire. But as bad as things were in Jack and Rachel's on again, off again relationship, the drawn out nature of Eric's unrequited feelings for Rachel was even worse.

Perhaps the most difficult part of this plot was the fact that, when they weren't romantic with each other in any way, Rachel and Eric actually did have a sort of adorable friendship, as perhaps the two dimmest bulbs in the friendship group. But Eric was left longing for Rachel far longer than the series should have allowed - even worse, considering they never let him find a true love all his own.

NEXT: Boy Meets World Stars Re-Stage Classic Cast Photo For 25th Anniversary

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