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This is not going to be a popular opinion.
I think the writers had some good intentions when they wrote this episode, and they really wanted it to be an emotionally powerful masterpiece. They had a coherent theme that flowed through every storyline except the boat: this was the episode where *every* character made some decisions about how to acheive the future stability and security they longed for. Ross broke up with Elizabeth because he realized he had no future with her. Rachel and Phoebe faced the idea that they didn't want to be alone when they were older, and tried to give themselves a guarentee. And Monica nearly broke up with Chandler because he foolishly allowed her to believe that she had no future with him. Monica and Chandler's story came the closest to working, but there were substantial flaws in every storyline they gave us this episode.
1. Ross and Elizabeth: Elizabeth joins the increasing line of SOs who suddenly go weird after several consistent episodes of pleasant maturity. I'd love to know what Professor Gotta Keep It Secret Geller was doing in her dorm room, anyway.
2. The Backups: I've got a huge beef with this one. We are expected to believe that after *all this mess*, after the reunions and the breakups and the messed up vows and the "I still love yous" and the marriage in Vegas and the whole thing with Jill... after ALL THAT......!
Ross and Rachel treated their prospective future marriage with the same casual abandon that Phoebe and Joey did. There was no glimmer of deep emotion behind the businesslike transactions. even though Rachel did trade for Ross' name. Ross actually did not care if he got Phoebe or Rachel, as long as he "didn't end up an old maid." That's very emotionally dishonest writing. As recently as nine episodes ago, Rachel asked Ross to keep away from her sister because the idea of them dating made her uncomfortable. The emotional residue of their past was there. That was believable. As recently as three episodes ago, Ross felt weird because Rachel went out with his girlfriend's father. That made sense. This needed to be rewritten. There needed to be some undercurrent that the two characters were either nervous about the prospective deal, or anticipatory, or if they were acknowledging, subtly to each other, that there was still the spark, or SOMETHING. Even refusal to do it because of their past would have been preferable to just ignoring it. This is really not my R&R side talking. I have recently found myself on a Niles and Daphne kick and don't care much anymore. They took an issue that was emotional dynamite and treated it like it was a game. Ross and Rachel are not Joey and Phoebe. Bad writing.
Now, as for the Big Deal...
I tried to like this one. I thought Matthew Perry was pretty good. He bounced back and forth with a rollercoaster of emotions and I wanted it to turn out for him. But there were severe problems with this story, not the least of which was that it was entirely made up of recycled material.
We've already dealt with Richard before. He caused the big fight between them *last* year, and for the most part, that episode was well handled. But here, I'm actually supposed to believe that, after *four years* apart from Monica, with whom he had a three month relationship, Richard is suddenly supposed to materialize with a marriage proposal the very same week that she's about to get engaged to a man she's been dating two years and living with for one.
And this actually gave Monica pause.
Can't make me think very highly of Monica's devotion, that's for sure.
She never once considered saying, "Chandler, remember that advice I gave Ross about Elizabeth? Well, it goes for you, too. If we have no future, we are over." But instead we got a very contrived conflict where the outcome was really never in any doubt at all and the big payoff was one of the most badly overacted, maudlin scenes I think I've ever seen on any sitcom. I agree that the little moment where Joey told Chandler she was gone was a nice little bit for Matt. The candles were good. Monica on one knee was good. But then they started crying, and it was so forced and obviously phony I was actually embarrassed watching it. My husband, who has *no* couple affiliation at all, groaned and got up to get a snack during that scene. Courteney Cox cannot act her way out of a wet paper bag that somebody has sliced with scissors. Emmy nomination for this? Uh....no.
I watched it again yesterday just because I felt I MUST have been too hard on that last scene. I wasn't. I did, however, figure out what they were trying to do and why it didn't work for anybody who wasn't a Chandler and Monica fan. This was an attempt to be the Anti Morning After. Ross and Rachel get into jealousy issues, Ross and Rachel break up in a very emotional scene that leaves them both crying. Chandler and Monica are sorely tried by jealousy issues, Chandler and Monica get engaged in a very emotional scene that leaves them both crying. . Cue the crying. Crying actually written into the script. Problem?
In TOW the Morning After, Jennifer Aniston was not supposed to cry. David's performance moved her so, and she was so caught up in the moment, that she cried involuntarily and the producers liked it so much they kept it in. That was a genuine emotional epiphany for the actors, the characters, and the audience combined. Here, Courteney and Perry were both directed to cry, and it was very obvious they were both pretending. Not one real tear to be seen anywhere. No real reason for the tears. (And yes, I've lived through that moment when you realize you will spend your life with the person across from you. I know EXACTLY how it feels.)
But as they go along their engagement journey, I will try to remember a much better, more effective, more honest, more enjoyable proposal that was among the best delivered lines of the fifth season.
Chandler looks at her warmly with all the feelings in his soul, crawls through the metaphorical tunnel, and says with all his heart, "It's a four."
Now THAT was a good, honest proposal scene.
One last note: One of the problems that this episode faces is that it immediately preceded one of the great emotional epiphanies for one of the great sitcoms of all time - Frasier. I actually thought this wasn't all THAT bad until I watched David Hyde Pierce go into action immediately after the Chandler and Monica show was over. The power that a really exceptional actor can produce from the smallest look, a slight tremor in the voice, a closing of the eyes, puts what we saw here in the engagement scene to shame.