MovieChat Forums > Sideways (2004) Discussion > if you're Miles....

if you're Miles....

posted 2 years ago by daveyh (623)
5 replies | jump to latest

....at what point do you draw the line with Jack's "shenanagins" ?
Even if, and I'd like to think most people wouldn't, but even if you're just about on board with him wanting to have one last, ahem, night of fun before his wedding:
(1) There's a time and place for that - it's not like he's getting with a stripper or dancer at his bachelor party. They're not on a wild weekend in Tijuana or Vegas.
What's more, they're in Miles' sanctuary, which, as Miles himself points out near the end, Jack has now ruined for him.
(2) By making his first night with Stefanie a double-date, it gets Miles directly involved in his deceit, and also means Miles has to live up (or down) to the lie that his book is being published. Plus Miles clearly isn't ready to date again, especially after Jack tactlessly broke the news about Victoria remarrying only a few hours earlier.
The tragedy for me is that Miles and Maya probably would have eventually gotten together anyway further down the line without Jack's interference.
(3) By Tuesday lunchtime, it's apparent that this isn't the one night stand he'd told Miles he was after. He's getting into a full blown relationship with Stefanie - spending all her free time with her, meeting her family, even bonding with her daughter, all while he's due to marry another woman just days later.
This is the point, for me, where everyone would say enough's enough. Even if he'd let things go that far, Miles should have left a note in the room for Jack and gone home on the Tuesday daytime while he and Stefanie were out for the day - by then of course he'd already had the (for him) disastrous double-date but cut your losses.
Things just snowballed from there. Miles was horribly used during that week - even on that last morning, if Cammy had turned out to be single, there's no telling when, or even if, Jack would have returned to the motel when it was the rehearsal dinner later on. Miles would have been sat there all day not knowing what was happening, if he needed to call Christine or her family to say they were running late etc.
Oh, and
(4), Jack announces that he wanted to have one last fling just 12 hours after he asked Miles if he thought he was doing the right thing getting married. That's a sign that if anything the wedding should have been called off, and again, it put Miles in a really difficult situation.

So yeah, original question - if you were Miles, when would you have put your foot down and told Jack to do one?

[–] DancingintheDark (1609) 2 years ago

I had a friend like Jack, in fact, he was my best friend in high school, I ultimately let the friendship go because it never stopped, the constant shenanigans, the using, exploiting, selfish behavior. I do miss him but in terms of our friendship, he consistently drained my cup, and one day a light switch was flicked and all of a sudden I had enough and wanted nothing to do with him, and I doubt I ever will.
And I’m cool with that.
Not sure if I answered your question, I don’t think I did.

I love the film Sideways and every time I watch it I can’t help but compare Miles and Jack, their personalities as well as their relationship to myself and my old friend. I’m an introvert and overly empathetic and my old friend, just like Jack, exceedingly handsome, extroverted, charming, lady killer, probably sociopathic, and exceedingly manipulative… he would pull the exact same type of shit that Jack did, it’s almost scary how closely the film resembles the dynamic of our late friendship, but there is a nostalgic feeling I get when watching Sideways, that or I’m laughing my ass off.

[–] daveyh (623) 2 years ago

I've had a similar experience. I've known a couple of Jack types too. I've learned that, over the years, a lot of these "cool guys" show themselves to be chancers and users and completely irresponsible. I've also observed that they tend not to have any like-minded friends who they view as their equals, instead they seem to have sidekicks. Or lackeys or monkey-boys or whatever you want to call them. The women in their lives also seem to be completely manipulated by them.

Like the saying that everyone's a socialist at 20 and a capitalist at 40, when you watch Sideways at 20 you think Jack's awesome and Miles needs to lighten up, then when you watch it again at 40 you realise what a selfish, feckless a**hole Jack really is. And this is coming from someone who identifies more with Miles personality-wise, both when this movie came out and now!

[–] Gd5150 (11747) 2 years ago

Miles did the right thing.

And we all benefited from the hilarious stories it reaped.

[–] daveyh (623) a year ago

true, would have been a very short movie had Miles gone home early. Plus Miles himself will have some hilarious stories involving Jack (and largely at Jack's expense) as a result of staying and putting up with Jack's shennanagins (still can't spell that word!).

[–] BourbonKing (5777) a year ago

Miles told Jack off by ditching the wedding reception, and likely his Best Man Speech, because he knew Jack's marriage was doomed. There's no indication of Miles' friendship with Jack after he returns home to San Diego and there's the impression of a period of time passing by. Miles eventually reconnected with Maya, so she didn't begrudge him.

If Miles ditched Jack during their getaway then this story ceases to exist. BTW, without Jack's presence with Miles at the restaurant, Miles and Maya would have ended up platonic acquaintances.