Definitely in S1 before he had his redemption conversion
I think he was trying to get to know her because of her superstardom but when they actually became friends I don't think he cared. He's always been the one to actually see her as she is. Charlie was definitely trying to make Avery think he wasn't on her level but it didn't work. What I would have wanted them to address is the money/class inequality between them. They dealt with it just a little when they first got together and he didn't want her buying dinner for him all the time, but they kind of dropped it. I always loved this dynamic between them and felt like it was fertile ground - before their marriage and the PPD - because Juliette is rich as sin but she doesn't care at all about money. Which is interesting because she came from NOTHING. You'd think she'd have a hangup about it but she doesn't.
On a kind of related note, I think one of Juliette's love languages is receiving (giving) gifts - this is how she expresses affection. From Deacon's dog and letting Avery use her studio to Halle's car. But it isn't Avery's love language (words of affirmation/acts of service) and so he took her buying dinner/accepting that Edgehill deal as an affront when she didn't mean it that way. They need to read that book.