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 are the only times Cory Matthews kisses another woman while committed to Topanga, he does flirt on other occasions.
Cory Cheats on Topanga With Missy Robinson
In Season 3, Episode 9, Missy Robinson kisses Cory in her parent’s basement. Cory agreed to attend her house for a party, but 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 the kiss but didn’t turn away. However, he comes clean to Topanga at the end of the episode, and although she scolds him initially, she forgives him.
Cory Cheats on Topanga With Lauren
The second and most famous time that Cory cheats on Topanga occurs in Season 5, Episode 20. Cory’s class attends a ski lodge field trip, which means Topanga, Shawn, and Angela also attend the trip.
Cory injures his ankle getting off the bus, and can’t ski with his friends. So he ends up talking to the lodge concierge, Lauren, all day and all night. Soon, a mutual attraction becomes evident for the pair, and they share a kiss. But, even though Cory admits to having feelings for Lauren, he tells her that he’s committed to Topanga.
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. Unfortunately, the letter falls out as he walks to the bus, and Topanga picks it up.
Topanga chooses not to read the letter initially, but Angela opens the envelope on her behalf in the next episode. Finally, after confronting Cory about the letter, he comes clean about everything. Soon though, Lauren arrives in Philadelphia to explore her feelings for Cory further.
Cory agrees to go out with her to test his feelings for Topanga. Even though Topanga wins out, she dumps him for having to test his feelings. As Topanga rightly points out, tons of guys hit on her throughout their relationship. She is the more attractive member of the couple and refused overtures consistently out of loyalty to Cory Matthews.
Other Potential Cheating Incidents From Cory
While Cory doesn’t kiss any other women besides the two 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. Of course, the whole thing was Shawn’s idea, but Cory ends up pursuing multiple women at the party despite being in a relationship with Topanga.
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 dance. But, unfortunately, he leaves his ring behind and has 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 causes Cory and Topanga to break up for a short period, they eventually get back together.
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 cheats on Topanga two times by kissing another girl while in a committed relationship. However, some argue that Cory also cheated on her in other instances, like when he removed his wedding ring at Club Cleaváge to avoid ridicule from his college friends.
Does Topanga Cheat on Cory?
The only time Topanga arguably cheats on Cory is in Season 3, Episode 12, The Grass is Always Greener. Although she doesn’t kiss another man, she misled Cory about her plans to attend another school’s party and pretend to be a French girl to gain male attention.
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.