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What Would Married Life Be for Jack? SPOILERS


Sideways posits Jack(Thomas Hayden Church) as a borderline successful TV and voice over actor who has used his fame, his brawn and his attitude to get a lot of women in his life.

As we meet him, he is about to be married in a few days and on a wine tasting and golf trip with his old college buddy Miles(Paul Giamatti) ...Jack elects to have sex with one more woman before marriage. He succeeds. He even deludes himself during the trip that maybe he will call off the wedding, switch to his new woman, and settle down with HER.

Maybe he would have settled down with the new woman, probably he would NOT have, but it is all made moot when the new squeeze finds out about the wedding and smashes Jack's face in with a motorcycle helmet, breaking his nose. "Goodbye."

And so , as "Sideways" ends, Jack goes through with the wedding --to a beautiful woman from a rich family. (He met his wife when she was a waitress, which is pretty much how he meets his wine trip woman, too.)

But isn't this the question going forward after the movie ends: What would married life be for Jack?

I doubt there is one of us who saw Sideways who believed that Jack would be faithful. He wouldn't. The issue would be how long could he hide his cheating? Would he manage to get paid enough by working with his rich father-in-law to "want to make a go" of hiding the cheating? Or would the wife find out soon enough and dump his ass?

At the end of Sideways, Jack's pal Miles arrives at the door of the woman who dumped HIM -- because she learned of Jack's cheating ways. Now the woman(Maya)is forgiving Miles and inviting him to visit. If Miles and Maya DO get together -- married or otherwise -- methinks that Jack will be "persona not grata" with Maya. No more good times for Jack and Miles as pals.

Sideways ends before any of these things happen. It is all speculation - which good movies create in us -- as we wonder "what happened next."

What would married life be for Jack?

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The answer would be in the novel sequel "Vertical" but I haven't read it. The synopsis on Wikipedia only mentions Jack's presence in some of the plot no mention of his marital status.

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Jack is divorced and depends upon Miles for support during the trip. Stephanie (Terra) is not in the book and the guys talk about how she is a "pay for play" girl in Reno.

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The answer is in the sequel, Vertical. It is probably exactly what you might expect of a man who cheats on his fiancee and whose fiancee also cheats on him (in the book).

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Ah..so the pretty fiancée cheats on HIM. Turnabout is fair play.

I wonder if she cheated on him during his trip to the wine country with Miles.

That said, I think we maybe have to go with the movie as we have it. The sequel book was never filmed.

I'm pretty sure that the marriage simply didn't last, and that cheating would be a reason why. Though also possibly work difficulties if Jack couldn't keep up his voiceover work.


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Yes she did cheat. Jack injured his ankle in the book, so Miles danced with the bride. Victoria asked Miles if Jack had cheated on her while the two men were on their trip. Miles lied and said no, but Victoria said that if Jack cheated, then it was fine as she also cheated (or words to that effect).

The book Vertical was very different than Sideways.

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Yes she did cheat. Jack injured his ankle in the book, so Miles danced with the bride. Victoria asked Miles if Jack had cheated on her while the two men were on their trip. Miles lied and said no, but Victoria said that if Jack cheated, then it was fine as she also cheated (or words to that effect).

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Well , there you go. Actually, it might have been a marriage of cheaters staying together for the sake of...society? Money? The parents?

Or the wife had the same thought as the husband: "One last fling."

But WOULD it be?

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The book Vertical was very different than Sideways.

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I may track it down, but since it will never be filmed, and not with the same actors looking the same way even if it is...I think I'll conclude the "Sideways" adventure with the movie as we have it.

Hopeful for Miles...

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Pickett has written screenplays for the two sequels to Sideways. https://www.hollywoodreporter.com/news/general-news/sideways-development-as-broadway-musical-1206537/

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