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Discover LudwigThe phrase "a difficult afternoon with" is correct and usable in written English.
You can use it to describe a challenging or unpleasant experience that occurred during an afternoon, often in relation to a specific person or situation.
Example: "I had a difficult afternoon with my colleagues as we struggled to meet the project deadline."
Alternatives: "a challenging afternoon with" or "a tough afternoon with".
Exact(1)
We knew it would be a difficult afternoon with him.
Similar(59)
It was a difficult afternoon for Annika Sorenstam, who began the day with a one-stroke lead.
The ref changed the game with a really poor decision that made it a difficult afternoon for everyone.
It's been a difficult afternoon.
Jones, who had a difficult afternoon, saw no foul.
It was a difficult afternoon for us.
West Brom boss Steve Clarke: "It was a difficult afternoon.
When we got here we were disappointed with the state of it and thought this was going to be a difficult afternoon".
For Joleon Lescott, in particular, it was a difficult night and he ended up looking like a man with two left feet.
Bryant had a difficult night and forced the action a few times but finished with 29 points and 8 assists.
It was a difficult morning.
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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