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How can I make this sentence more natural?

Asafisan

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5 Jun 2023
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Hello!
I tried to talk about my weekend evening (it is Friday in my country) and wrote this:

金曜日の夜、私の友達全員が誰かの家で過ごす予定だったので、私は通りがかった友達の一人に家まで迎えに来てもらえるか頼んだ。彼は「問題ないよ」と言ってくれました。しかし、なぜか彼は私が冗談を言っていると思っていたので、私を迎えに来なかった。」と聞いたら、「どこにいるの?」と聞いた時には既に遅く、彼はすでにみんなと一緒にいました。

The last phrase "と聞いたら、「どこにいるの?」と聞いた時には既に遅く、彼はすでにみんなと一緒にいました。" feel a bit unnatural. Maybe it's because I used both と聞いたら and と聞いた時には?

If you could tell me by the context how could I rephrase it to be more natural, I would appreciate it.
The meaning it should convey - It was already too late when I asked him where he is because he was already there (with everybody).

Thank you
 
1. Make sure your verb endings are consistent. If you end your first sentence with 頼んだ, you should make an effort to use the だ ending for all your sentences.
2. I'd break up the first sentence into two sentences, because I somehow feel you've got a lot of information in that one sentence. 予定だった feels like a natural ending place. 私の友達全員 already sounds as if they are excluding you. Might be more natural to say 友達と一緒に (leave the 私の off because its understood). Or maybe 友達とみんなで
3. And for the next bit, 私は通りがかった友達の一人 sounds a bit too much like English translated one-for-one into Japanese. 私はその一人に or 仲のいい一人に etc., might be more natural.
4. 迎えに来て → 連れって行ってくれるようにお願いした or 乗せてくれるように might be more natural in this first sentence. (Again, I'm not a native speaker so YMMV). For some reason I find 迎えに来る not as good in this case as 連れって行く or 乗せて行く. But for sure it is OK to use it. I just find the other ways somehow more fitting.
5. I feel it would be more natural to say しかし、金曜日の夜、遅くなっても彼は迎えに来てもらえなかった (or 彼は現れなかった = he didn't show up). Then explain why - because it feels like the "punch line" of the story is that he thought you were joking. So it feels like that should be at the end.

彼に連絡して「どこにいるの?」と聞いたら、彼はすでにみんなと一緒にいたんだって。
どうも私がお願いした事は冗談だと思ってたらしい

or something like that.
 
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1. Make sure your verb endings are consistent. If you end your first sentence with 頼んだ, you should make an effort to use the だ ending for all your sentences.
2. I'd break up the first sentence into two sentences, because I somehow feel you've got a lot of information in that one sentence. 予定だった feels like a natural ending place. 私の友達全員 already sounds as if they are excluding you. Might be more natural to say 友達と一緒に (leave the 私の off because its understood). Or maybe 友達とみんなで
3. And for the next bit, 私は通りがかった友達の一人 sounds a bit too much like English translated one-for-one into Japanese. 私はその一人に or 仲のいい一人に etc., might be more natural.
4. 迎えに来て → 連れって行ってくれるようにお願いした or 乗せてくれるように might be more natural in this first sentence. (Again, I'm not a native speaker so YMMV). For some reason I find 迎えに来る not as good in this case as 連れって行く or 乗せて行く. But for sure it is OK to use it. I just find the other ways somehow more fitting.
5. I feel it would be more natural to say しかし、金曜日の夜、遅くなっても彼は迎えに来てもらえなかった (or 彼は現れなかった = he didn't show up). Then explain why - because it feels like the "punch line" of the story is that he thought you were joking. So it feels like that should be at the end.

彼に連絡して「どこにいるの?」と聞いたら、彼はすでにみんなと一緒にいたんだって。
どうも私がお願いした事は冗談だと思ってたらしい

or something like that.
Wow, I really appreciate your detail answer!
I think I understand all of your points. It is still hard for me to not literally translate from English.

Thank you very much!!
 
しかし、なぜか彼は私が冗談を言っていると思っていたので、私を迎えに来なかった。」と聞いたら、「どこにいるの?」と聞いた時には既に遅く、彼はすでにみんなと一緒にいました。

The last phrase "と聞いたら、「どこにいるの?」と聞いた時には既に遅く、彼はすでにみんなと一緒にいました。" feel a bit unnatural.
There are two major problems there.

1)
You didn't put the opening square bracket, and only put the closing one after 来なかった。.

2)
彼は is the topic, so the subject of 聞いたら is interpreted as "he", not "I(i.e., you)".


しかし、なぜか彼は私が冗談を言っていると思っていたので、私を迎えに来ませんでした。「どこにいるの?」と聞いた時には既に遅く、彼はすでにみんなと一緒にいました。
 
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