S4 E15 — ‘Chick Like Me’
Cory: Well Shawn, I don’t want you take this the wrong way, but… you’re kind of a babe.
When Cory decides he wants to be a hard-hitting journalist and write about life from the perspective of a woman, it’s up to Shawn to pretty-it-up and go on his first date as a lady. This episode is laugh out loud funny as Cory remains his dorky self in a dress, and Shawn pulls off the part of demure yet sexy Veronica with ease. What’s hilarious is that this episode is basically all of Cory’s fantasies come true: Shawnie as a hot girl? What a babe.
S4 E21 — ‘Cult Fiction’
Shawn: If I was an empty person who didn’t have anything to believe in, I might go with you, because that would be easy. Well, I’m done with easy. And I’m done with empty. I’m done with you.
Poor Shawn has always been a kid without a solid support system, and Cory’s seemingly perfect life is a reminder of everything he doesn’t have. He’s the perfect target for a cult looking for lost souls, and after drinking the Kool Aid for a hot minute, Shawn snaps back to reality when his former foster parent, Mr. Turner, ends up in the hospital in critical condition. This episode is really powerful in showing how easy it is to get caught up in a cult crowd, and the leader, Mr. Mack, manages to seem terrifying, despite never actually saying anything too troublesome. The ending itself is a tearjerker, as Cory forces Shawn into a hug to remind him that genuine love can’t come from empty gestures, and overwhelmed with fear in losing Mr. Turner, Shawn finally breaks down and prays.
S5 E7 — ‘I Love You, Donna Karan (Part 1)’ and S5 E8 — ‘Chasing Angela (Part 2)’
Topanga: Stop it! You’re afraid of getting to know someone, and you’re afraid of someone getting to know you, and unless you get over this you’re going to go through life all alone! Except for Cory, who will bring you magazines and pudding.
This is the episode where Shawn falls in love with a purse! After keeping a strict two-week dating rule so that he never has to get hurt, Shawn finds the purse of his “perfect girl,” and immediately falls in love, even though Cory and Topanga insist that his infatuation can’t be real because he’s fallen in love with an idea, instead of a person. When it turns out that the purse belongs to Angela though, Shawn knows that he has to swing for the fences if he’s going to have a shot with the girl of his dreams. Angela’s introduction in these two episodes is a real delight, as she both fits in with the group right away, and brings a blunt, practical charm that’s different than what they’re used to. She’s so breezy and effortlessly cool! She also inadvertently turns Shawn on into poetry and writing when he finds her book of sonnets! Angela teaches Shawn about the importance of getting to know a girl for who she is first, instead of just focusing on the superficial.
S5 E13 — ‘The Eskimo’
Mr. Feeny: I’m talking about the boy in the crowd. Look at the one holding up the sign!
Alan: Which one?
Cory: The one that says, “Hey Feeny. Nothing’s impossible.”
Fed up with the trio’s antics, Feeny gives them an assignment they’re all destined to fail at: Shawn has to get Superbowl tickets, Topanga has to butt out, and Cory has to help them both. Deeming the assignment impossible, they all decide that they’ve figured out the week’s lesson: to try. But Mr. Feeny doesn’t want them to just try — he wants them to succeed. And on his path to success, Shawn realizes that he’s always been his own worst Eskimo — he has to believe in himself to make it, it’s not enough for other people to believe for him.
S5 E17 — ‘And Then There Was Shawn’
Angela: Well is anyone of us safe?
Shawn: Yeah, virgins! Virgins never die!
Cory (to Topanga): All right! Thanks for saving me.
Eric: I’m dead.
Jack: I’m dead.
Shawn: I’ll get as sick as you can get without actually dying.
Simultaneously hilarious and terrifying, Shawn’s horror-comedy dream has fun with every cliché from the teen horror genre—including a special guest stint from Jennifer Love Hewitt as Feffy! A wonderfully original Halloween episode, “And Then There Was Shawn” is always one of the most memorable Boy Meets World episodes.
S5 E19 — ‘Eric Hollywood’
Shawn: Cory’s my best friend… but I want to tell you to your face that if I knew that you and I weren’t friends anymore, it’d break my heart too.
While Eric and Mr. Feeny journey to a weird alt-version parody of Boy Meets World called Kid Gets Acquainted with the Universe, Topanga tries to salvage her friendship with Shawn amidst her and Cory’s breakup by nursing him through the chickenpox. The Eric scenes are delightfully self-aware as the cast plays extreme versions of themselves, but the Philly scenes with Shawn and Topanga remain genuinely sweet as they show the struggle of picking sides with friends amidst a breakup.
S5 E24 — ‘Graduation’
Shawn: I could’ve done better. That’s what I wrote. That’s how I feel. I’m sorry. I could’ve done better. Congratulations to those who did.
A celebration of Boy Meets World’s five previous seasons, the season 5 finale brought back the classics while also propelling us in the future. Frankie and Joey, the Cory and Shawn of the underworld were back! Minkus was competing with Topenga for Valedictorian! Mr. Turner got a shout out! And meanwhile, we got to be excited about where our regulars were going to be headed into season 6 as well. Eric was his full-on crazy self in trying to stop Mr. Feeny from retiring, and Jack was in quintessential older sibling mode trying to force Shawn to be excited for graduation (“Why don’t you appreciate my caricature of you with a big head and tiny body and you’re riding the big diploma like it’s a magic carpet ride to your future?”) And Shawn, despite five years of academic apathy, finally gets his head in the game with his beautiful graduation speech — it’s a sign of his beginnings on the path towards becoming a writer, and how in college he evolves into an academically competent student once he starts caring. And of course, in the final shocking minute, academically-driven Topanga risks it all to propose to Cory, the love of her life.