Cory cheats on Topanga twice in Boy Meets World. The first time with Missy Robinson in Season 3, Episode 9: The Last Temptation of Cory, and the second time with Lauren in Season 5, Episode 14: Heartbreak Cory.
While those episodes are the only instances of Cory Matthews kissing another woman while committed to Topanga, Cory does flirt with other women in additional episodes.
Cory Cheats on Topanga With Missy Robinson
In Season 3, Episode 9: The Last Temptation of Cory, Missy Robinson kisses Cory in her parent’s basement. Cory previously agreed to attend her house for a party, not knowing that Missy’s invitation was a ruse to pursue him romantically.
As Shawn explains, Cory has “the scent” because of his relationship with Topanga — meaning women find him more attractive now that he’s in a serious relationship.
Cory was not expecting Missy’s kiss but did not turn away either. At the end of the episode, Cory comes clean to Topanga, who, while disappointed in him, decides to forgive him for his transgressions.
Cory Cheats on Topanga With Lauren
The second and most famous time that Cory cheats on Topanga occurs in Season 5, Episode 14, Heartbreak Cory. The entire class attends a ski lodge field trip, which means Topanga, Shawn, and Angela also attend the trip with Cory.
Unfortunately, Cory injures his ankle while getting off the bus, preventing him from skiing with his friends and classmates. As a result of being stuck inside, Cory ends up talking to the lodge concierge, Lauren, all day and all night.
Soon, the pair’s mutual attraction becomes evident, and they later share a kiss. While Cory’s attraction to Lauren is genuine, he reveals to her his commitment to Topanga. However, Lauren seems unbothered by his existing relationship.
Cory Keeps His Interaction With Lauren a Secret
After asking Shawn if he should come clean to Topanga, Shawn urges him not to tell her about the kiss. At the end of the episode, Lauren gives Cory a letter that he puts in his suitcase, but it falls out on his way to the bus, and Topanga picks it up.
Despite choosing not to read the letter initially, Angela Moore opens the envelope on Topanga’s behalf in Season 5, Episode 15: First Girlfriend’s Club, the next episode. Topanga reads the entire letter and confronts Cory about its contents.
Topanga Confronts Cory on His Interaction With Lauren
When confronted with the evidence, Cory admits to everything that happened with Lauren. To make matters worse, Lauren arrives in Philadelphia in Season 5, Episode 16: Torn Between Two Lovers (Feeling Like a Fool).
Lauren’s unexpected arrival further complicates Cory’s efforts to reconcile with Topanga. However, in an odd twist, Cory agrees to go out with Lauren to test his feelings for Topanga. His reasoning is even more nonsensical in retrospect.
Topanga Dumps Cory for “Testing His Feelings” With Lauren
After an enjoyable date with Lauren, Cory, and Shawn unscientifically compare the two women using jellybeans and a balance beam. Cory concludes that while he likes Lauren, he cannot live without Topanga.
When Cory reveals his conclusion to Topanga, she dumps him anyway. As Topanga rightly points out, countless guys had hit on her throughout her relationship with Cory, and she consistently refused those overtures for him.
Other Potential Cheating Incidents From Cory
While Cory doesn’t kiss any other women besides those mentioned above while committed to Topanga, he does engage in other strange behavior for someone in a committed relationship. For example, take a look at these famous instances below:
Cory Pretends To Be Shawn Hunter
In Season 3, Episode 12, The Grass is Always Greener, Cory attends another school’s party and pretends to be Shawn Hunter. While the whole thing was Shawn’s idea, Cory enjoys his newfound persona and pursues multiple women.
Cory and Topanga had been dating since Season 3: Episode 1: My Best Friend’s Girl and were apparently in a rut by Episode 12.
Cory Removes His Engagement Ring
In Season 6, Episode 8, You’re Married, You’re Dead, Cory attends Club Cleaváge with Shawn, Gambling Dan, and Louie, who tease him for being an engaged college student. They call him the major, which is short for a major wuss.
Cory removes his wedding ring at the club to avoid further ridicule and finds himself surrounded by several attractive waitresses during a provocative dance. Later he realizes that he left his ring at Club Cleaváge and goes back to retrieve it.
What Season Does Cory Cheat on Topanga?
Cory cheats on Topanga in Season 5 with Lauren, a ski lodge concierge who attends to Cory after he sprains his ankle. However, Cory also cheats on Topanga in Season 3 with Missy Robinson.
While Lauren’s emergence prompts Cory and Topanga’s Season 5 break up, they get back together later in the same season.
What Episodes Does Cory Cheat on Topanga?
Cory cheats on his girlfriend Topanga in Season 3, Episode 9, The Last Temptation of Cory, and in Season 5, Episode 14, Heartbreak Cory.
How Many Times Did Cory Cheat on Topanga?
Cory definitively cheats on Topanga two times, both by kissing another girl. However, some argue that Cory also cheated in other instances, like when he removed his wedding ring at Club Cleaváge to avoid ridicule from Gambling Dan.
Does Topanga Cheat on Cory?
The only time Topanga arguably cheats on Cory is in Season 3, Episode 12: The Grass is Always Greener. Topanga lies to Cory about her plans for the night so that she can attend another school’s party while pretending to be French.
Topanga quickly becomes the talk of the party, as most of the male attendees contend for her attention. Aside from being attractive, Topanga pretends not to be able to speak English, adding to her mysteriousness.
Ironically, Cory attends the same party pretending to be Shawn Hunter and pursues multiple women while at the party. The pair decides to split at the end of the episode, though their separation proves short-lived.