Dear Penny: Is My Underachieving 52-Year-Old Boyfriend Using Me?

A man sleeps on the sofa with a dog sleeping on him.
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Dear Penny,

My boyfriend is a bit of an underachiever. He’s 52 and makes $15 an hour working about 25 to 30 hours per week. He has his paychecks garnished for back child support. He says he was injured and couldn’t work much when his kids were growing up, so he only nets a couple hundred a week. He lives with his parents and doesn’t pay for food or rent. 

Meanwhile, I’m a single mom earning over $100,000 working two jobs. I’m not super rich because I have college-age kids to support and a pretty sizable mortgage. I paid off my boyfriend’s past debts, his cell phone bill, his auto insurance and all our dating expenses, such as entertainment and eating out. It’s getting expensive, and I’m going into debt. 

I miss being able to go on a couple of decent vacations each year. (He says he will go with me, but he has zero funds to contribute.) He really is a sweet man who treats me really well, but I’m starting to resent this arrangement. Is he using me?


Dear S.,

Maybe your boyfriend is using you, or maybe he’s just really lazy. You’ll never know with 100% certainty what’s going on in his head. Regardless, though, it sounds like you feel used in this relationship. Don’t dismiss that feeling.

Another glaring red flag you shouldn’t ignore is your boyfriend’s delinquent child support. Do you believe he did the best he could to provide for his kids? If the answer is no, RUN. Someone who shirks their responsibilities as a parent is unlikely to be a good partner.

Let’s assume you still want this relationship to work, though. The easiest way to figure out if your boyfriend is using you is to close your wallet. Quit paying for dates. And for heaven’s sake, do not pay this grown man’s bills again. Tell him the truth — which is that you need to cut back on expenses because this relationship is putting you in debt. If your boyfriend is using you, he’ll bolt pretty quickly.

But if he’s simply lazy, he may stick around, even if he doesn’t put much value in your relationship. Sure, he’ll be disappointed that his girlfriend is no longer functioning as his ATM. But sometimes lazy people linger in relationships because they’re getting entertainment and affection. If you dumped him, your boyfriend would need to find these things elsewhere. That requires at least a modicum of effort.

What you need to do is test whether he’s willing to match your effort once you take money off the table. If he does value the relationship, this is a perfect opportunity for him to prove it. Ask him to take turns cooking dinner for each other at home or planning inexpensive date ideas. See if he can come up with something better than Netflix and chill.

Outearning your significant other doesn’t necessarily spell doom for a relationship. What often is a deal breaker, though, is when your work ethics are completely out of sync. You obviously have goals if you’re driven to work two jobs and earn six figures on top of being a single parent. But some people are content with keeping themselves fed and clothed, even if it means living with their parents forever and never climbing out of debt.

Though you say your boyfriend is a sweet man who treats you well, don’t give him too much credit. It’s easy to be pleasant when someone caters to you, especially when you also place zero expectations on them.

Should you decide to continue this relationship, it’s essential that you keep your finances separate. That means no co-signing for him, no paying his bills, and no moving in together.

And once you’ve paid off the debt that you’ve accrued from this relationship, please take one of those vacations you’ve been missing. Even if you’re still with your boyfriend, there’s no rule that you have to travel together. You can take a solo trip or travel with a friend or go on a group tour. Don’t put your life on hold in hopes that your boyfriend will morph into a financially responsible adult.

Ultimately, you have to ask yourself whether you’re willing to continue things more or less as is, with you footing the bill for every splurge. Maybe you enjoy his companionship so much that you’re fine with that. But it’s also OK to decide that you want to build a life only with a partner who shares your ambition.


Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to [email protected].