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I want to ask my friend about how his relationship with a girl he's with is going. Are these completely natural:

How's it going with Hannah?

How's it going with you and Hannah?

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    These seem fine -- I think you could also say "How are things going with Hannah/you and Hannah?"
    – Kman3
    Commented May 24, 2020 at 19:24
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    Or "how are things between you and Hannah?" (Not better, just an alternative) Commented May 25, 2020 at 13:03

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Both are fine.

In future, you will progress faster if you don't worry too much about being "completely natural". You can't ask about every phrase you speak so get used to making mistakes -- mistakes are one of the most natural things in language!

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