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Yea, TOW The Flashback was the episode that really made me really appreciate Chandler/Rachel in a romantic context, but I saw TOW The Cheesecakes before I watched that (I came into the show late), and I loved the friendly dynamic and chemistry they had. I didn't know they had kissed in earlier episodes, so it was just a crackship of mine that I didn't take seriously because of Chandler/Monica and Ross/Rachel. They're my two favorite characters, so that played a part in my love for them too. I just loved how FUNNY they were together, and for a sitcom, you want that. Then I saw TOW The Stripper Cries, and it went from crackship to actual-ship-even-though-I-knew-it-would-never-happen.
I actually think I read once that the writers were planning on putting them together, then decided against it? Or they were part of the original plan when they created the show?
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They're my two favourite characters, too; so I think that also played a part in why I started shipping them, also as a crackship. TBH, I still kind of refer to them as a crackship of mine, because Ross/Rachel are my otp of the show. But, at the same time, while I do also ship Chandler/Monica, I have more interest/ship Chandler/Rachel more than them. So, maybe that takes C/R past the crackship level.
Does that make any sense?
Yeah, I also read that about the writers having initially intended to put Chandler/Rachel together. The main couple for the show was going to be Joey/Monica; and the first season was going to focus on them. Chandler was only meant to be more of a secondary character (along with Phoebe), but something was to eventually happen between him and Rachel.
I wish I could remember the exact places I read all of this from. I know some of it was mentioned in the recent Vanity Fair article, but I don't think the part about C/R was mentioned in that.