That's tough. I mean, I"m really close with one of my exes, but she was NEVER the type to need rescuing or need "to be pushed to get a job." Like... if she needs to be harangued by her friends into functional adulthood; she isn't "a positive influence in his life" to begin with. He's definitely emotionally invested (which isn't all together bad, we'd want that in our friends) but if it comes down to "Keeping a date with you or going to rescue her"... that is when you know above all where his heart truly lies.