Broke boyfriend prioritizes drugs over job-hunting

Carolyn: I’ve been with my boyfriend for a little over a year and everything’s been great. He’s loving, caring and understanding. Our relationship, overall, is healthy.

But recently I have started noticing a growing resentment toward my boyfriend because I’m always paying for most things. When we go out to the movies he’ll pay for his ticket and I’ll pay for my ticket, the snacks and the food if we go out to eat after because he doesn’t have any more money. At school, he’ll only have a dollar or so for the bus, so I’ll pay for his lunch. One time, he asked if I wanted to go eat at McDonald’s, so I assumed he was going to pay and left my wallet at home. When we got there he realized he only had $3 and asked if I had brought my wallet.

He doesn’t have a job, and when he looks for one he doesn’t try very hard, it seems. He says no one wants him because he doesn’t have experience or a car, but he doesn’t bother to go jobhunting. He just applies to a few places online. He has a car, but he lost the key to it about a year or two ago and it doesn’t work anymore due to the fact that it’s just been parked in his driveway. Instead of saving up his money, he spends it on weed.

This has been going on since the beginning, but it just started bothering me and it’s starting to affect our relationship. I do love him and I don’t expect him to pay for everything all the time, but it would be nice if he would take me out on a date at least once where he pays for everything without worrying if he’ll have enough. I have brought it up to him and he was very understanding and said he’d work hard to change, but I feel like until he finds a job, this resentment will keep growing. Am I shallow for this?

— Anonymous Anonymous: Your boyfriend is a loving, caring, understanding person who barely functions.

Singeth my forehead, “Hello keyboard my old friend.”

And no, it is not “shallow” of you to regard it as a setback that his car is a driveway ornament and being high is his top priority. Your misgivings are, on the contrary, the most promising thing about your letter, because the rest has me afraid.

Why are you doubting yourself? Why so little respect for your own feelings? Why are you backpedaling on legitimate concerns?: “I don’t expect him to pay for everything all the time … ”?

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.

Carolyn: 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? — C.

C.: 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.