Yeah seemed reasonable enough to me
Didn't spoil anything, really enjoyed this movie
Great heartfelt characters

it didn't seem in the movie like they were miles away. the whole wine country seemed tight and it seemed logical that two "wine country working girls" would know each other somehow. never seemed a stretch to me, and I'm always looking for a stretch.
The Fearmakers Blog
https://thefearmakers.blogspot.com/

I'll take your word for it
Ha - well done.

Interesting! As someone who has been accused of being "too" honest, I'm not much of an authority on these things so I'll take your word for it.

Jack has a low understanding of how things work, and how people react. He knows saying he lost the rings won't fly, and he knows saying a drunk hit him at a tasting will lead to questions - were you flirting with his girlfriend, etc.
OTOH, the car is "proof" of an accident.
People who lie as often as Jack or Miles develop an instinct for these things.

Even though I understand your point, this has never bothered me, maybe because Sandra Oh made it seem so plausible. I wasn't even bothered by the implausibility of Miles breaking into the house to get the wallet. The one thing I found implausible that did bother me about the movie was that Miles and Jack had to wreck the car to explain the broken nose. It would have been so plausible and so easy for him to say that he got hit by some really drunk guy at a tasting.

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I know what you mean. I would say normally that wouldn't happen like that in life. In rare occasions I suppose it could, and the movie just happen to "catch" one of those rare occasions.

"If you put your mind to it, you can accomplish anything." -George McFly

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I don't think it's really a flaw as it doesn't really hurt the quality of anything in the film, it's just writing something to make the story development move quicker and help pacing.

It is not some massive area of California. They work 9 miles away from each other. I don't know how it is where you live but in California where we don't walk, 9 miles is next door neighbors. Stephanie works at a renowned local winery and no doubt Maya has been to and probably frequents all the local wineries in the area. She's a huge wine enthusiast and studying horticulture because of said interest in wine culture. Frankly I would be surprised if they HADN'T met. Not to mention, they have a lot in common, both divorcees, both seemingly in their mid 30s. Both in the service industry. They both share a great love of wine. I agree with you that Stephanie's reaction should have had a little more surprise and wonder in it when they mentioned her friend Maya but again, very probable they would know each other.

But it's not likely. And the lack of shock between Stephanie, Jack and
Miles plays contrived, plain and simple.

Maya's a huge wine fan. Stephanie works at a local winery. It's not implausible that their paths would have crossed at some point.

I live in Santa Barbara and I just want to mention that The Hitching Post, which is in Buellton, and the wineries around Los Olivos (I believe when they meet Stephanie they are around there) are quite near each otherit's not a large area at all. So considering they are both way into wine and live and work in the tourist industry in the same lightly-populated area, they probably move in the same circles so I don't think it's so implausible at all that Maya and Stephanie know one another.
Luke this is your father come set the table for dinner.

No it's not extremely contrived. And now that I read the script of that part again it pretty much does everything you just said it should do.
And it's a film anyway- sometimes you do have to just let things roll by without making them 100% realistic.

Sorry, it plays extremely contrived, possible or not. This is a huge
area of Central and Northern California and Jack says the line as though
he's expecting Stephanie to know her. She responds without shock or
surprise. It would've played better if she had said something like, "Oh, my
God - I KNOW Maya. Very well, in fact", with Miles responding with,
(genuine surprise) "You're kidding. How weird is that?"
The way the scene plays is so rushed and written, as though the
screenwriters just wanted to get that contrivance out of the way to move
the plot forward.
Think about it: This is no different than you being friendly with a
waitress in some ordinary restaurant, then driving 15 miles away to a
K-mart and casually asking some clerk if she knows the waitress.
Possible? Of course. Likely, no. The scene makes me roll my eyes every
time I watch it, despite how truly great this film is.

Really? Life is full of coincidences. I worked with someone for the first time a few weeks ago and it turned out that a week later we were both going to be visiting our brothers who both lived over a 1500 kms away and only 20 minutes from each other in a pretty random part of Australia.
The coincidence you speak of in Sideways is hardly unbelievable. In fact it's not even that remarkable. It's natural that two women working in the same industry not too far from each other could be friends.