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Here is the sentence:

Let the users spend more time playing this game and make the users come back often after their first-day of gameplay.

When I try to omit the "of" like this, the grammarly app tells me not to do so.

Let the users spend more time playing this game and make the users come back often after their first-day gameplay.

Well, when I read the sentence, I feel that omitting the "of" is all good. May I ask when two words need a preposition between them?

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    Think about it this way: do you want the users to come back after the day, or after the gameplay? It might seem like the same thing, but the original sentence says "I want them to come back after the first day (in which they played the game) and your change says "I want them to come back after their gameplay" and "first day" is simply modifying "gameplay".
    – stangdon
    Commented Jan 3, 2023 at 13:42
  • So both sentences are legal but are delivering different meanings?
    – AGamePlayer
    Commented Jan 4, 2023 at 11:42
  • They're both grammatically correct, yes. I think "first day of gameplay" makes a lot more sense, because you're saying that you want them to come back another day.
    – stangdon
    Commented Jan 6, 2023 at 21:12

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There is no general rule for 'when two words need a preposition between them'.

I don't know why first-day is hyphenated here, but a day of [something] means a day spent doing that, or one when something was happening all the time (a day of rain). So their first day of gameplay is the first day they spent playing the game. You could also say their first day's gameplay. It doesn't sound idiomatic without either of or the possessive.

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