Only the complicated irony of this episode is that hooking up with a more vibrant, energized, “perfect” version of Miles isn’t what she wants, after all.
The couplet from the song that “Piña Colada” most strongly evokes, however, is this one: “I didn’t think about my lady, I know that sounds kind of mean / But me and my old lady, had fallen into the same old dull routine.” Now set aside the creep factor of calling a romantic partner your “old lady” - though Styx did an entire song around this, which made for maybe the most awkward (yet sweet) scene in all of Freaks and Geeks - and you’ve got Kate’s marital dilemma in a nutshell. ( “I’m the love that you’ve looked for, come with me and escape.”) She also comes to the realization, in the end, that maybe she already has what she’s seeking. Kate and Miles 2.0 have placed the modern equivalent to a classified ad in the form of Da8er profiles, and Kate is on the lookout for someone new, who turns out to come in the extremely familiar form of her husband. (The narrator responds to the ad while lying in bed next to its author, for example.) But this episode of Living With Yourself reflects that song to such an uncanny effect that it feels like a straight adaptation - one that, surprisingly, dignifies Holmes’s lyrics.
People have noted that the song is a little creepy. The surprise ending is that the woman he meets is his current partner, which in Holmes’s telling affirms that neither of them had to look outside their relationship at all. The gist of the story is that a man bored in his relationship responds to a classified ad that mentions, among other things, the requirement that he must like piña coladas, and he arranges a meeting with the ad’s author at a bar called O’Malley’s. Everyone knows the chorus to the soft-rock standard “Escape (The Piña Colada Song)” - “if you like piña coladas, and getting caught in the rain” - but Rupert Holmes’s 1979 single tells a three-verse story with a twist, which suggests his future work as the author of Broadway musicals like Drood and Curtains.
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