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I have seen the expression "land in the tall grass" and I am unsure of its meaning. Googling for it, I can only get the literal meaning, but not the one from a context like the one below from a TV series:

He is the one who should be nervous, Mommy. If you ask me? George Altman landed in the tall grass.

Any ideas?

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We may need a little more context. It looks like the sentence doesn't have any metaphorical meaning attached to it. I think George simply landed in the tall grass. – Noah Nov 24 '12 at 13:45
I think the meaning is related to the feeling of the situation when you land in the tall grass. You can't see what's around, lots of confusion. You also don't know where you're going. – Rikki Rockett Nov 24 '12 at 13:50
Yep, without context it's hard to know what it means, but the tall grass is sure a lot softer than the rocks that Roald Dahl landed in when his plane crashed in the North African desert back in WWII. – user21497 Nov 24 '12 at 14:15
More context: From episode "Ryan's Song" of the comedy Suburgatory. Here's the subtitles. – Hugo Nov 24 '12 at 14:16
I would sure like to see what kind of person uses both "mommy" and "in the tall grass" in the same speech. – tylerharms Nov 24 '12 at 14:44

To "land in the tall grass" comes from golf. It means to hit your ball out of bounds, or at least into the deep rough on a golf course instead of on the fairway, from which it would have been easier to hit.

The expression is used figuratively here. Obviously, they're not playing golf, but "George Altman" appears to be in some kind of predicament.

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After reading the transcript of the scene, I would say that "in the tall grass" is a slightly more obscure way of saying "in over your head."

The context of the scene seems to be that a woman who is well-seasoned in dating handsome, wealthy, successful men is suffering anxiety over a date with this George Altman fellow; and her daughter (?) is calming her down by reminding her that she is the experienced one and George Altman is the one who should be nervous about a date with such a classy lady.

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I have always assumed that this metaphor (and land in the long grass) comes from golf, where a ball that misses the mown fairway is much harder to play.

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