What's the meaning of "それはそれで どうなんですか？"?

Question

I usually try to figure things out on my own and have never asked a question on this site before. But I ran into a difficult sentence in an anime and feel completely overwhelmed. I know my question is long, but I would appreciate it if you could try to answer it.

The sentence is this one:
それはそれで どうなんですか？
The official translation is "I'm not sure if you should be okay with that."

I learned not so long ago that the formation XはXで (which I encountered in これはこれで) means "X in its own way", but I couldn't translate the sentence with that. So I checked and found on jisho.org that それはそれで meant "in that case; (might not be what was expected or hoped for but) if that's the case".
What? Two different meanings? (If it's the same meaning, then I'm already lost.)

And I still can't translate the sentence. Here are the two possibilities, literally:
"That, in its own way, how is it?"
or
"If that's the case, how is it?"

When I encountered これはこれで, alone, "good" was implied : "This is good in its own way."
So I tried something like :
"That, in its own way, (how) is it good?"
or
"If that's the case, (how) is it good?"
I feel like I'm close, but something is still missing...

If the sentence was something like "それはそれで どうなんですかね" (with ね), then I would have this connotation of doubt:
"That, in its own way, I'm not sure."
or
"If that's the case, I'm not sure."
But it's NOT どうなんですかね, and I'm still far away from the official translation. And I'm not sure I understand the sentence, even with the context!

Here are the few lines of dialogue that precede it, if you need context:
A (shy girl, still lives with her parents):
きっと 20年先も 花ちゃんと私は一緒だし
それに 私は ずっとあの家にいるから
いつでも来てね！

B (花ちゃん):
それはそれで どうなんですか？

Could you explain to me why それはそれで has two meanings (apparently ?) and what the meaning of the whole sentence is (and why it has that meaning)?
Usually I don't try to translate, just to understand, but here I am scratching my head...

(If you need to know, I'm kind of at N3 level right now, more or less. I'm not sure because I'm self-taught and I know a lot of N1/N2 stuff. I don't usually have too many problems with anime, but sometimes I come across this kind of insurmountable obstacle, and it's really demoralizing. :/)

Thanks in advance.

Answer 1

The correct approach is "That, in its own way, how is it?". This それはそれで indicates that the suggestion/opinion/statement has its own problem.

• Xはダメですが、Yも問題です。
  X is no good, but Y is also problematic.
• Xはダメですが、Yもそれはそれで問題です。
  X is no good, but Y, in its own way, is also problematic.
• Xはダメですが、Yもそれはそれでどうなんですか？
  X is no good, but what about Y on its own? (It has its own issues, doesn't it?)
• それはそれでどうなんですか？
  → I'm wondering if it has its own issue. / That's another problem by itself!

From context, B is probably saying that, while it's true that she's worried about their future friendship, A living with her parents for another 20 years is a different problem in its own right.

---

I don't think それはそれで by itself means "if that's the case". But it may work as a possible translation in certain contexts:

• 行きたくないの？ じゃあ、それはそれで。
  He doesn't want to go? Well, if that's the case (that's another option / I'm fine with it)...

Here, something like それはそれで構わない is implied.

Note that それはそれ has other usages, too.