Broke boyfriend prioritizes drugs over job-hunting
Why are you backpedaling on legitimate concerns?: "I don't expect him to pay for everything all the time ... "? Did you really proofread your letter and worry readers would think you were greedy, for thinking it might be nice if your boyfriend invited you to McDinner only if he had the $10 to pay for it?
And why is your main concern about this ("healthy"?) relationship that he doesn't pay for popcorn at the movies? It's like saying patients' main problem with stage 4 cancer is that their hats no longer fit.
I'll be the first to agree that greatness takes many forms, and if your boyfriend is in possession of such greatness of companionship, moral support, affection, wisdom, laughter, and burdensome-chore completion that having to be his money source is totally worth it to you, then I'd say to embrace him as-is and go in peace.
But your resentment is telling you that you're not getting enough out of this pairing to justify what you're putting into it. And the only answer to that is to listen carefully to what your better judgment is trying to say.
How do you tell whether the right thing to do with a friend who is giving you the cold shoulder is to confront the issue with him/her, or to be your normal kind and friendly self when your paths cross and hope it sorts itself out? Sure, with a very good friend you would discuss it. But with a more casual friend you risk making interactions more uncomfortable and maybe come away more disappointed.
My husband says let it be. I'm more the type to confront problems, but I'm not sure it's done me any good in my life. What are your thoughts?
I think you're both right.
There's always a chance your friend's "cold shoulder" is not about you, but instead is a bad mood that slipped its leash. It happens to the best of us. So, it's a kindness to be flexible enough not to react to every exchange with friends that's a little off.
If it happens enough with this person to be a pattern, then that's your cue to say, "Is everything OK? I get the sense you're unhappy with me," or similar.
That is, if you care enough about this casual friendship to recover it; it could just be running its course. Don't confront others unless you're sure you actually want what you're asking of them.
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