Wow that’s really helpful, obviously that’s correct considering it’s a native source and all. Unfortunately, two different grammar sources (including maggie sensei) mislead me by stating that ない+げ is done via なさげ. Just goes to show I should start using native resources more often for grammar. Much appreciated thank you 
My girlfriend says that なさげに does not sound wrong to her ear… so this might be a prescriptive vs. descriptive thing. Where なげに is “correct” and なさげに is what you’re more likely to hear.
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Is this an accurate understanding of the difference between these two questions?
バレンタインデーに何か上げたことがありますか。
Did you give anything on valentine’s day?
バレンタインデーに何を上げましたか。
What did you give on Valentine’s day?
The first one means “Have you ever given anything on Valentine’s Day”
The second one means “What did you give on Valentine’s Day”
Are you familiar with the ～たことがある grammar point?
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I am familiar, yeah. I think I just suspected some magic here, that it would be referring to a specific Valentine’s day instance. I don’t have a good reason for suspecting that.
If you just wanted to talk about the most recent Valentine’s day then it would be
バレンタインデーに何かをあげましたか。
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Didn’t want to come back here any time soon, but I gotta embarass myself with questions yet again, sorry. I was floating through Berserk ch.360 when some spirit started talking through the girl’s body while using some ancient words. Presumably even ancient grammar.
「ものはゆげな 童女〔わらはめ〕の 祈事〔ねぎごと〕」
At https://kobun.weblio.jp/ you can easily find out that 童女 = 女の子 and ねぎごと = 願い事.
But what is「ものはゆげな」? As I see it, ゆげな is probably some い-adjective which has ～げな attached. But I can’t confirm that cuz I can’t find any ゆい adjectives. In fact, I spent 2 hours searching all I can to only find myself trapped in the dead end! What can it be?
The example sentence for 焦燥 is: 度重なる事業の失敗で、すっかり焦燥しきっているんだ
What is the meaning of しきっている?
Have you tried verbs and NA adjectives? My J-J dictionary has plenty of verbs beginning with ゆ that would fit the grammar. Dunno about the context though.
Ok this might be very wrong, but my first thought was 面映い which obviously has the wrong reading, but the “suffix” kind of fits? My dictionary doesn’t list 映い as a separate word, but there is an entry for
映し: まばゆい。また、きまりが悪い。(embarrassed, ashamed)
That doesn’t really explain the もの or the げ conjugation, but maybe the conjugation is also valid for old 〜し adjectives? Who knows. It at least makes sense in the context of describing a girl?
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Yes, I tried to find any NA adj. which fits or any V which may fit. For V it has to be some ichidan verb, so る disappears and ～げな replaces it, but I found none, 揺る is godan. And none of NA adj. were found. Show me your dictionary.
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I very well like your thoughts because I was dancing around 面映い for some time but didn’t find it possible to separate 映い just like you.
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I was being an idiot 
Is there any way to distinguish the on’yomi reading that’ll be used with jukugo 日 based on context?
I’ve noticed the patterns that go with other alternate kanji readings; such as げつ being used for “month” in a nondescript-sense, がつ being used for specified months and つき being used to refer to the moon itself., But so far with 日 it seems entirely lackadaisical in whether it uses にち or じつ. It’s irking me and I keep getting jukugo readings turned around as both readings are used just as frequently.
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Outside of the exceptional 今日は, I can’t think of a time it ever takes the にち reading outside of day/date counters (except for 2-10 and 20) and 日曜日. 毎日 you could lump in with those day/date counters.
For the ひ/び reading, you can generally expect it to pop up any time a day is appended as a unit to something else that’s a fixed occurrence, where you could break up the first part of the compound and it would still have meaning on its own. Weekdays. 誕生日、登校日…
じつ tends to pop up for day-related compounds that aren’t fixed events, but more descriptions, I suppose. 先日、嘉日、祝日…
At the end of words perhaps. For the beginning of a word, there’s also 日常, off the top of my head.
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It’s true. 
I forgot about all the times it’s used as a stand-in for Japan, too. (Always にち.)
“結局、その場その場で丸暗記するしかないことが多い。”
https://open.mixi.jp/user/7552023/diary/1959305993
You can suss out trends, but at the end of day, for kanji that frequently used, a lot of compound readings just come down to what era the phrases entered Japanese in, as that article concludes. There isn’t always a practical, logical reason behind it.
Wanikani also has 日没 and 日欧.
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I guess it depends on whether “just memorize each word” or “look up the era the word came from” is more practical!
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