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"she's so irresponsible, how could she possibly live a life like this?"

He actually didn't say it like that. But I think it's healthy for him to recognize the chaos in her life and realize getting drawn into it would be counter to the hard work he's done to make his own life less chaotic. And people shouldn't be beating him up for making that (sane) decision. Even if he DID say ILU already. People are acting like he's obligated to stick with her and work it all out and he's not! This is dating. Yes, he should slow his roll in the future but he's hardly the only person here who has jumped into something too quickly. (T, stop with the romantic weekends away btw! Save that for later!)
That's why I think it's good to have a larger discussion about what people mean when they say ILU and where they think the relationship should be before they say it. So far I've heard 6 months and "whenever you feel it". But if people are saying it's a very serious commitment to say it, then should we wait longer? Or should we acknowledge that it isn't necessarily the same thing as making a very serious commitment?

His observation was that this wasn't about her being broke, but about her being broke AND fiscally irresponsible AND relying on daddy to bail her out from bad decisions. That would be a dealbreaker for me any day. I think it's healthy that he recognized that it's a dealbreaker for him too now.