Kelso’s Cheating: Point Place Continuity™
The show was known to retcon events or add in events we never saw or heard about on-screen until later, like Kelso getting “a little side action” from a girl from Sacred Heart while he was sleeping with both Jackie and Laurie.
On Jackie and Hyde’s double-date with Kelso and Brooke (“I’m a Boy” [6x08]), we learn Kelso slept with other girls when he and Jackie were “on a break” when Jackie was annoyed at him. No reason for her annoyance is given. Neither is a time for this break, which is the more important detail.
The relevant dialogue from the episode:
Kelso: I only cheated on [Jackie] with Eric’s sister. Well, and then the rest of the girls when we were on a break ‘cause I annoyed her. But none of those girls were anybody’s sister … uh, except for the two that were sisters.
This line makes absolutely no sense with what actually happens on the show. Jackie breaks up with Kelso the first time when she learns that he made out with Pam Macy. The second break-up happens after her pregnancy scare. The third breakup happens when Jackie catches Laurie and Kelso kissing. The fourth breakup happens when Kelso realizes Jackie makes him feel badly about himself. The fifth and final breakup happens when Kelso runs away to California.
He was already cheating on Jackie during S1-S2 with Laurie and a girl from Sacred Heart. So the cheating he discusses in the above line of dialogue had to happen during their S3-S4 relationship, which makes little sense because that was Kelso’s growth arc. He’d actually felt remorse for cheating on Jackie – and took responsibility for it – and was shown to be honest and monogamous toward her. To fit this “break” and more cheating into J/K’s relationship timeline means Kelso is – unbelievably – worse than he already is.
After Jackie confesses to her one kiss with Todd (“the Cheese Guy”), which she didn’t initiate and was tricked into, Kelso acts like she had sex with another guy. But according to “I’m a Boy,” Kelso must have cheated on Jackie (again) before then with multiple girls, not just one girl, which must have happened over a period of weeks.
Kelso has no legs to stand on, to begin with when he breaks up with Jackie in “Everybody Loves Casey” (4x26). The writers, again, create an incident that never happened on-screen:
Kelso: Remember the first time I kissed Pam Macy?
Kelso: Earlier that day, I didn’t have any money to buy you Tater Tots. You said that I’d never be able to support you, ‘cause I wasn’t smart enough.
We never hear about this incident until Kelso tells Jackie when he breaks up with her – and we definitely would have heard about it in “Ski Trip” (1x13). Kelso’s friends are so angry at him for (potentially) messing up their weekend at Jackie’s ski cabin that Kelso would’ve confessed: “I only did it 'cause I had no money to buy Jackie Tater Tots, and she said I wasn’t smart enough to support her. So I went and made out with Pam Macy, which was awesome! Come on – what else was I supposed to do, not make out with her? It made me feel better!”
At the end of season 4, Kelso blames his cheating on Jackie for making him feel badly about himself. But what we actually get on-screen during the series is, yes, Jackie expressing her frustration and disappointment in him when he screws up – often insultingly. But Jackie is also his biggest supporter in his dreams, vs. his / their friends, in pretty much everything. She bolsters his ego as much, if not more, than she puts him down.
But his argument doesn’t hold water either way. He’s still responsible for his cheating. He could’ve broken up with Jackie if he felt verbally and emotionally abused by her. Jackie also shows no awareness that Kelso cheated on her again during their S3-S4 relationship, but her reaction to his statement in “I’m a Boy” is a facial expression that can be interpreted several ways: mild surprise, annoyance, disbelief he’d talk about his cheating in this manner, or all of the above.
Ultimately, though, the new information Kelso (and the writers) inject into his a and Jackie’s tlimeline is a continuity mess, created for the purpose of a joke with no consideration of characterization and the show’s timeline.