I've said this on some other videos, but I find it ironic that Claire alone stopped Dylan's proposal to Hayley while Phil just sat and said/did nothing and in the finale of this season, Phil was 100% on Claire's side and had her back in trying to discourage Hayley from moving in with Dylan until they found out from Luke that she got into college.
I think its bc he honestly never minded the idea of Haley ending up with Dylan- he always liked Dylan, right from the start (makes sense considering how alike they are). With the moving in with Dylan- I think he just genuinely thought that she was too young, top it off with him feeling uneasy about them being intimate (which had nothing to do with Dylan, more so to do with Haley herself). Even with the proposal- if Haley did supposedly say yes, I'm pretty sure Phil would've asked Haley to wait and stay engaged until she was older, but that's just a theory.
