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The phrase "a pretty difficult time" is correct and usable in written English.
It can be used to describe a challenging or tough period someone is experiencing.
Example: "After losing his job, he went through a pretty difficult time adjusting to the changes in his life."
Alternatives: "a quite challenging time" or "a rather tough time".
Exact(5)
It has come at a pretty difficult time for Roy Hodgson.
In "Garden State" Andrew never learned how to swim and has a pretty difficult time jumping in the pool.
Before the ACA's passage, Congress and the Administration had had a pretty difficult time keeping Medicare costs in check, in part because of political opposition to necessary reform.
ThIn arthele originally appeared on VICE US.
We thought it might be an honest mistake after all, Shepard Fairey probably has a pretty difficult time keeping his ear to the ground between all the album artwork and celebrity guitars and culture-jamming Bush out of the White House but an anonymous insider told us, "The whole office was against using that picture, but Shepard insisted on it.
Similar(55)
We went through some pretty difficult times.
"You know that she came through some pretty difficult times, as many people who are breaking down barriers did".
Those were pretty difficult times, but perhaps not as rancorous as the era of fierce combat in which we now live, a legacy from the bitter battles over the Supreme Court nominations of Robert Bork and Clarence Thomas, and the impeachment of Bill Clinton.
And we've had some pretty difficult times together, but in the 31 years we've worked together, there is no one I have ever worked with that is more a man of his word or a person of his word than John McCain, Reidd told reporters Tuesday afternoon.
"Jim was having a pretty hard time.
It's a pretty funny response, but the general consensus it prompts amongst most of the class is that this is a measure that punishes "ordinary" people, both banged up and on the outside, for whom buying a can of Fanta is a small moment of affordable enjoyment in what is at times a pretty difficult slog.
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com