And I believe that a lot of these... issues of his stem from an extreme lack of self confidence, as he really just wants attention.
That's what I thought too.
He parks his self esteem in other places and he wants the strokes/attention to feed/feel it rather than sit his booty down to look inward because he doesn't want to park it there.
Could choose to REALLY work on the self esteem thing and learn to validate HIMSELF so he can be his own self esteem generator instead. But doesn't at this point. Not ready to go there -- I have no idea what baggage he's carrying.
(Frankly, I don't care. You are both still internet strangers to me but so far I see you doing the hard work of personal growth, so I'm more sympathetic to you. I know it burns. Hang Time at the Forge. And here you are, trying to suck it up and roll. Kudos, BTW!)
You build self esteem by doing esteemable things. In this case -- owning your own freakin' bag no matter what it costs you, being a person if integrity, a person of your word.
Making honest, deliberate intentional choices, and OWNING the consequences of the choice(s) you made!
Not running away from the "feels uncomfortable" that goes with taking a real stand on something. Not flying willy nilly by the seat of your pants.
Changing from "I want everyone to like me all the time" to "I want everyone who matters to me to like me most of the time, and forget about the rest! They can like me or not like me, I do not care for they do not matter most to me!"
I hope for his sake he's ready to own his own bag. It's not going to be fun Hang Time for him. He's been putting OFF and putting OFF so his Hang Time will thus be all the longer. But better now than never. He's making himself his Morley's chain and sooner or later he'll have to wear the burden.