Grammar Trainwrecks

[cranefly]

During today's writing session, I took pause after this masterful scrawl (yep, I can scrawl with a keyboard):

"He was creepy in every respect, impossible to get comfortable with around."

The structure fascinates me.  Two prepositions at the end.  (I'm pretty sure "with" is being used as a preposition.)

Rephrasing often brings enlightenment (and intelligibility).

He was creepy in every respect, and it was impossible to get comfortable with him when around him.

That's just plain unwieldy.  I'm letting my original stand.  For now.

[Greg]

How about ' with him around'?

[cranefly]

Sounds good, Greg.  Sometimes you just gotta simplify.

I think my fascination was that I was overlooking the obvious -- a blind spot right smack dab in the middle of it all.

[Drunk Monk]

That sentence needs to end with more prepositions with at of for.

That wasn't something I sent you to edit at, was it?

[cranefly]

DM, you give me such an easy out.  But gotta be honest; it came from my own stuff -- my latest story, "Strident Embraces," which I'm about two weeks from finishing up at.

[Dr. Ivor Yeti]

On my first reading of the sentence in question, my brain edited your original version to Greg's suggestion.