How Charlie’s Relationship With The Waitress Should End On ‘Always Sunny’

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When It’s Always Sunny In Philadelphia premiered in 2005, it didn’t take long for the show to establish one of it’s most prominent recurring bits: Charlie’s relentless pursuit of The Waitress. In the very first episode, “The Gang Gets Racist,” he has his first of many awkward encounters with her. This time, she hears Charlie drop an n-bomb, and assumes that he’s a racist, when he was actually recanting a story of someone else using that word. That misunderstanding left a terrible impression of Charlie that he has spent the entire series trying — with absolutely no success — to erase.

The most memorable episode in the Charlie-Waitress saga is almost certainly “The Nightman Cometh,” in which Charlie stages a nonsensical play designed for the sole purpose of convincing The Waitress to marry him. We remember this episode for the general ridiculousness of the songs, and of course, the famous “boy’s soul/boy’s hole” bit, but what’s most important is the very end, when The Waitress rejects Charlie in front of everyone. His play is yet another miserable failure with The Waitress.

Just for a second, let’s compare what happens in “The Nightman Cometh” to what happens in the famous Futurama episode, “The Devil’s Hands Are Idle Playthings.” In each episode, a dumb-but-perpetually-optimistic character stages a grand production to win over an unrequited love. In Fry’s case, he writes a beautiful opera thanks to the Robot Devil’s magic hands, and in the end, Leela is enraptured. In Charlie’s case, he writes the worst musical of all-time (okay, it’s kind of the best, too), and the object of his affection is more repulsed by him than ever. Really, the difference between It’s Always Sunny and Futurama is the difference between fantasy and reality. Don’t get me wrong, I totally cry at the end of “The Devil’s Hands Are Idle Playthings,” but if you tried this in real life, your fate would probably resemble Charlie’s a lot more than Fry’s.

Of course, at one point, Charlie almost does convince The Waitress to change her mind about him, and how that played out may have been the cruelest joke of all. This is what happened in “The Gang Goes To The Jersey Shore.” On their trip to the boardwalk, Charlie runs into her, and they end up having a beautiful evening on the beach together. She apparently finds him more charming then usual. It looks like after all this time, all those rejections, Charlie has finally won her over.

Then, she wakes up the next morning believing that Charlie must have drugged her, and feeling more creeped out by him than ever. Charlie decides to take his minor victory, and just enjoy that he got to spend the night with her, but really, this was arguably his biggest humiliation over the entire saga. What looked like the breakthrough he had long been hoping for turned into yet another failure, and his odds of ever-changing her mind were now next to impossible.

Let’s make one thing perfectly clear: many of the things Charlie has done in pursuing this woman are emphatically Not Okay. He’s not just incredibly creepy, he does several things that are illegal, stalking this poor woman at every turn. I could totally understand why someone who had been stalked in the past would feel no sympathy for Charlie after his many terribly misguided actions.

At the same time, Charlie’s behavior is part of why he is by far the least evil of the central characters on It’s Always Sunny. He has no idea he’s doing anything wrong here. Is it because he’s too stupid? Too crazy? Too obsessed? The answer, of course, is all of the above. On a show full of characters who are willfully evil, Charlie is accidentally evil, putting this poor woman through years worth of unwanted attention because he doesn’t know any better, and because he genuinely believes that each gesture, hell, each interaction will be the one that finally convinces her to see things his way. Much like most of what happens on It’s Always Sunny, it’s hilarious in an incredibly dark, often sad way.

The show is going into its tenth season, and while it’s already been renewed for two more, there has to be some talk going on about how it will finally wrap things up. I’ll say one thing for certain: if It’s Always Sunny ends with Charlie and The Waitress finally getting together, I will be sorely disappointed. This is a show about the miserable realities of the human experience, and I hope it stays true to that form right till the bitter end.

I have nothing against the happy universe where Fry finally gets together with Leela, but that’s not what this show does. If it ends with Charlie taking things one step too far, and doing serious jail time? Now that would be the type of ending that this tragic twisted tale of obsession deserves.