There is so much that's great about this episode that it's difficult to find aspects to criticize. So many reviews (and virtually all of the User Reviews here) dwell completely on the likability of the character of Diane and why she left the show (one suggesting the writers drove her away???) and whether the series was an improvement as a result that there's no mention of the quality of the episode.
This episode is easily one of the finest in the show's history.
In the olden days when Cheers first ran, the romance of Sam and Diane was constant water cooler talk and a source for People magazine stories. There were rumors of Shelley Long leaving the show, so they even filmed three different endings to try to throw reporters off the scent. But she was leaving a successful show in which she was a star and - like just about every single sitcom out there, by definition - there were, of course, a limited number of places they could take her character. In one ending, they were married; then this ending; the third ending was never revealed. I'm guessing they might have killed her off; that's the only ending I can imagine them not wanting to admit.
This episode was written by Glen and Les Charles, the creators of the show who had started out writing for another fine television show, M*A*S*H. The literary devices they used in this show were ingenious; in particular, Sam's fantasy when he tries to anticipate whether Diane might someday regret never having written her novel.
It's easy to say nearly 40 years later, "but women can hold down a job and still have a family! She could have written her novel anyway!" and of course that's true; however, it does not play with the deck that the writers were dealt: Shelley Long was leaving, period.
Furthermore, the character of Diane Chambers DID care about typical homemaking items like drapes and china patterns and duvet covers. Over the five years she'd more or less been with Sam, I believe, Diane had become more traditional in her life goals and desires. For someone who was supposed to be such a serious-minded feminist, she threw tantrums over having her engagement ring box in her hope chest. She was a fashionista. And so on. PLUS ... what had she written in the five years she'd been with Sam, aside from poetic letters to him?
Throughout her five years in the show, Diane Chambers was more of a dilettante than an artist. Given the task to write Long out of the show, Glen and Les Charles went all the way back to the pilot and pulled out Sumner as an excellent bookend on the Diane era, teasing out old threads of her writing dreams as the *one* *thing* that might be strong enough in her heart to break her away from Sam. That was genius.
Then there was the task of doing justice to the Sam and Diane romance. Glen and Les Charles gave us, in under 5 minutes, a pretty realistic idea of what Diane and Sam had to gain by going through with the marriage - as well as what they would lose if she walked away. The fantasy sequence showed us who they could become over decades of marriage - and it gave them a device to illustrate with heartbreaking realism what Diane's leaving - again - would do to Sam. That was genius.
Sam's act of love and sacrifice, his wisdom in understanding that Diane's writing would soon consume her passion as he once had, rang through in his poignant last line: "Have a good life." That was genius.
Even the song choice for the closing fantasy dance - Irving Berlin's "What'll I Do" - spoke to the emotional loss dealt to Sam. Berlin wrote the song as an ode to a young woman he loved and wanted to marry whose wealthy father sent her away to break them up, and the song was likelier to have spoken to the 1987 audience. That, too, was genius.
(Although I came to prefer "Forever Love" by Luke Rackers, the moving piano music selected to replace it in syndication, "What'll I Do" has meaning that echoes the longing of the episode.)
The backdrop of the entire bar making bets on whether Diane was even "capable of saying I do," while the Justice of the Peace looked on with dismay, was clever comic relief to Sam's vacillation.
I also believe the loop the showrunners threw the show for at the beginning of season 6 was a perfect follow-up to an episode that was an emotional wildfire, but that's for another review.
As someone who can relate to looking back on life and wondering about "the one who got away," I admire so much the Charleses' ability to bring to life the idea that Sam had the wisdom to foresee the impact Diane's leaving would have on his life. Their work in this episode made it look much simpler than it was.
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