While Leonard had plenty of terrible moments in The Big Bang Theory, it was one fateful Halloween special that saw the sitcom’s hero start down a dark path. While Sheldon was unashamedly grating in both The Big Bang Theory and Young Sheldon, his roommate Leonard was always a sneakier sort of character. Leonard was initially established as the put-upon hero of The Big Bang Theory, but as the show continued his character flaws became harder and harder to ignore.

Well before he ended up with The Big Bang Theory heroine Penny, Leonard had a dishonest streak that would come out from time to time. This flaw was at its most egregious in one Halloween episode of The Big Bang Theory when Leonard cheated on his long-distance girlfriend rather than breaking up with her. Years before Leonard admitted that he also cheated on Penny in The Big Bang Theory’s season 8 finale, the character proved he was no angel in The Big Bang Theory season 5, episode 7 “The Good Guy Fluctuation,” when he cheated on his short-lived love interest Priya with a comic book artist named Alice.

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When Leonard First Cheated In The Big Bang Theory

Leonard, Priya, and Sheldon on the couch

In The Big Bang Theory Halloween episode “The Good Guy Fluctuation,” Leonard feels tempted to cheat on Priya when he meets Courtney Ford’s Alice, a fellow geek who draws comic books. Despite his usually stern outlook (inherited from Sheldon’s mother Mary in his Young Sheldon origins), it is Sheldon who accidentally gives Leonard the advice that convinces him to cheat on Priya. Leonard gets cold feet after kissing Alice and admits he has a girlfriend, prompting Alice to storm out. However, in classic sitcom fashion, when he admits this to Priya, she reveals she had also cheated on Leonard by sleeping with her ex. Despite this punchline, in character terms, the damage was already done.

Why This Moment Changed Leonard’s Persona

Leonard holds Penny near the apartment's busted elevator on Big Bang Theory

Like Ross of Friends or Ted of How I Met Your Mother, The Big Bang Theory’s Leonard always rubbed some viewers up the wrong way. A self-proclaimed nice guy, he tended to be self-pitying and resentful which didn’t always make for a likable lead character. However, much like the death of Young Sheldon’s George Sr made The Big Bang Theory’s version of Mary Cooper into a meaner, more stubborn figure, Leonard’s first foray into infidelity made his character less misguided and more outright self-serving. While his lapses into moping were forgivable, Leonard’s choice to cheat instead of breaking up with Priya was simply selfish.

The character’s inexperience in relationships made his early romantic screw-ups sweet and understandable, but his decision to put the moves on Alice before even breaking up with Priya proved Leonard was no longer the lovable loser that The Big Bang Theory originally introduced. By season 4, he was capable of playing two love interests off each other, and the fact that Priya turned out to be even more duplicitous than him didn’t make Leonard’s character shift any less noticeable and unwelcome. The Big Bang Theory’s central friend group was always the show’s main selling point, and making one of the co-leads of the series a callous cad was a shift that The Big Bang Theory never really recovered from.

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