Dear Penny: Should I Dump My Financially Irresponsible Jerk of a Boyfriend?

Dear Penny,

My boyfriend and I have been together for seven years now. Unfortunately, we are not doing too well financially and are paying off debt with a debt relief company. Even with this, we still struggle to get by. 

I make $40,000 a year. He barely makes $30,000 a year as a construction contractor who isn’t even on a W-2, so his taxes are very expensive come tax season. He also purchases cigarettes and weed on a weekly basis, which is a chunk of change as well. He claims he wants to get ahead, but he won’t budget or look for a better job. 

What should I do? I've tried talking to him, but he gets defensive about this stuff and then walks away. Should I just end the relationship because he’s not willing to grow up? 

-Stressed Girlfriend

Dear Stressed,

The problem with being in a relationship with someone who won’t grow up is that you feel more like a parent than a partner. It’s been seven years. Based on what you’ve told me, I’m not holding out hope that your boyfriend will change his ways.

Your boyfriend is detached from reality if he expects his financial situation to get better without making changes. But what bothers me most isn’t the cigarettes or the weed or the refusal to plan for the giant tax bill he gets every single year. It’s the fact that his response when you express concern is to walk away from the conversation. That suggests a problem that goes way beyond money.



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I’m in favor of dumping this guy unless he’s given you some reason to think he’ll turn things around. But I get it: Breakups are hard, particularly when you’ve been together for years.

If you’re not willing to end things just yet, you could see if he’s willing to make a small change instead of asking for a complete overhaul. It’s understandable why you’d want him to look for better-paying work or stop wasting money on smoking. But switching jobs or giving up a long-term habit can be enormously stressful.

You could start with something that’s less likely to put him on the defense, like telling him how stressed you feel every year at tax time. Independent contractors are supposed to make tax payments each quarter instead of waiting until tax season to pay, but you can make payments as frequently as you want. Ask him if he could start paying his taxes each week or on paydays so that you won’t be panicked next year at tax time.

Compared to changing jobs or giving up a smoking habit, this is a relatively small ask. If your boyfriend still isn’t willing to budge, he’s sending you a clear message that things will never change. As long as this relationship continues, your odds of achieving financial stability are pretty much non-existent.

I think you should start prepping your finances now, assuming that you are going to end this relationship. If it’s possible to save a little extra, either by cutting back or working extra, do it. Be sure to keep the money in a bank account that’s in your name only. If you don’t think you’d be able to afford your current housing on your income alone, look around at alternatives in the area. You may want to ask around to see if anyone you know is looking for a roommate.

I’m not sure whether you’re enrolled in a joint debt management plan or if the debt is in one person’s name. If you’re jointly liable, you may want to ask the company you’re working with if it’s possible to separate your debts. Given your boyfriend’s poor track record for managing money, I wouldn’t trust him to make his share of payments should you split.

Sometimes people need an impetus to change. Your boyfriend is clearly comfortable with letting you absorb the stress of his decisions. Perhaps a breakup would give him a much-needed kick to grow up already.

Regardless, your boyfriend’s days of holding you back are numbered. Either he learns to act like an adult, or you’re gone.

This was originally published on The Penny Hoarder, which helps millions of readers worldwide earn and save money by sharing unique job opportunities, personal stories, freebies and more. The Inc. 5000 ranked The Penny Hoarder as the fastest-growing private media company in the U.S. in 2017.

Make Money – The Penny Hoarder 2022-01-18 15:37:23

You can now order four free at-home COVID tests from the federal government, regardless of whether you have health insurance. A new website, covidtests.gov, went live on Tuesday, Jan. 18, one day ahead of schedule.

The website allows every home in the U.S. to order four free rapid antigen tests that deliver results in 30 minutes. PCR tests aren’t available. Tests are expected to ship within seven to 12 days, according to the website.

How to Get 4 Free COVID Tests

Signing up for your free tests is incredibly simple. All you need to do is go to covidtests.gov and provide your name and address, plus an email address if you want shipping notifications. And that’s it.

The U.S. Postal Service will deliver the tests. Currently, the website limits you to four free tests for each residential address, no matter how many household members you have.

Technically as of Tuesday, the website was in beta mode, which means it’s being tested for possible hiccups. Though there have been concerns that the website could crash upon launch due to high demand for tests, the site appeared to be functioning early Tuesday afternoon. A staff writer for The Penny Hoarder placed an order for testing kits without issue.

A health worker grabs two at-home COVID tests

What About the 8 Free Tests Insurers Have to Provide?

As of Jan. 15, health insurance companies are required to pay for eight home tests per month for each person covered by the plan. However, many people are still finding that they need to pay out of pocket for the tests and submit a receipt for reimbursement.

You can access four free tests for your household using the federal government’s website regardless of whether you have health insurance. The website doesn’t ask for insurance information, and no upfront payment is required. For now, the four free tests are a one-time only offer.

What if I Can’t Wait for My Test?

The earliest you can expect to receive your test through the federal website is late January. If you need a test before then and you have private insurance, you can pay for a home test and then get reimbursed for any upfront payment. The challenge, of course, is finding a home testing kit.

You can also access free and low-cost tests through a community testing center. To find a site, use HHS.gov’s testing center locator.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. She writes the Dear Penny personal finance advice column. Send your tricky money questions to AskPenny@thepennyhoarder.com.

This was originally published on The Penny Hoarder, which helps millions of readers worldwide earn and save money by sharing unique job opportunities, personal stories, freebies and more. The Inc. 5000 ranked The Penny Hoarder as the fastest-growing private media company in the U.S. in 2017.

Dear Penny: I’m So Frugal I Make My Own Toothpaste, So Why Am I Always Broke?

Dear Penny,

College was a struggle for me. As a student with a learning disability, I struggled and school took longer. When I graduated with my master’s of arts in 2008, the economy collapsed, and we went into survival mode. 

After 10 years of struggle, I FINALLY found my dream job, which is part time. Now I have a second job that uses my master’s degree, but it’s only 10 hours a week. With family help, we were able to buy a house. With two jobs, I am finally able to start paying on student loans and not defer them. 

We are struggling to stay on a budget with three kids. With increasing prices for basics, we find ourselves back in that space of struggle, overdraft and panic. We've tried using budgeting apps and find them confusing or hard to keep up with. 

We have done everything we can to survive: We got our grocery budget down by eating a lot of rice and lentils, by getting eggs from a friend and milk from a local farmer. We use free apps and the library for streaming apps. We make our own toothpaste. We are thrift store champs for clothing. 

But… I want savings. I want a future. I want to know I can one day retire. So, how do I do that? How do I get started?

-J.

Dear J.,

People don’t go broke from buying grocery store eggs and name-brand toothpaste. What you have isn’t a spending problem. You clearly have an income problem — meaning you aren’t bringing in enough income to pay for basic expenses and save for the future.

There’s only so much you can cut from your variable expenses, i.e., the ones like groceries, clothing and entertainment that you have some control over on a daily basis. Your fixed expenses, like housing, transportation and student loans, tend to eat up a much bigger chunk of your budget, and they’re a lot harder to cut.



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You have two part-time jobs. But two part-time jobs often don’t add up to one full-time job in terms of compensation. You may not qualify for benefits like health insurance or a company 401(k) match when you’re not a full-time employee. Career advancement can also be hard when you’re a part-timer. That’s not to mention the brain drain that often comes with working two jobs.

You don’t say what subject you earned your master’s degree in. But it sounds like it’s not in a particularly lucrative field.

So you need to ask yourself some tough questions. Would you rather work your dream job or a job that offers financial security? How important is it that your job actually uses your master’s degree?

If you earned your master’s in a discipline like arts or social work, you may need to accept that a better-paying job may not take advantage of your degree. That’s not to say you’ll never use the skills you acquired from your education. But you may need to shift gears and look for jobs that don’t require your specific degree.

Taking a hard look at your current jobs is going to be difficult. You finally found your dream job after a decade of struggles. You made significant sacrifices to earn your master’s degree, and you’re still paying for your education.

Keep in mind that most people aren’t working their dream jobs. That doesn’t mean they don’t pursue their passions. It’s entirely possible to work a full-time job because it offers good pay and benefits, and then do what you love on the side. There are countless 9-to-5ers whose true passion is blogging, podcasting, volunteer work or playing in a band.

As you figure out your long-term career path, you still need to get a handle on managing your day-to-day expenses. Since budgeting apps aren’t working for you, I’d suggest something called the cash envelope method. Essentially, you keep paying bills like your mortgage and student loans as usual, but you withdraw cash for your variable expenses. Then you label an envelope with each budget category.

For example, you might have separate envelopes for groceries, clothing, gas and pet expenses. You put the amount of cash you’ve budgeted for each category in the envelope. If you run out of cash for that envelope, you’re done spending in that category for the month. Only in a true emergency do you turn to your debit or credit card.

This approach can help you avoid overdrafting. Sometimes it helps people identify areas where they didn’t realize they were overspending. But I suspect that in your case, this method will highlight the difficult reality so many Americans are facing right now, which is that income is the problem.

There’s so much you’ve done right here. You’ve found creative ways to be frugal, while still providing for your family. You own a home. You’re making progress on your student loan. Now it’s time to take stock of how to maximize your income, even if that means your passion won’t be your full-time job.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to AskPenny@thepennyhoarder.com or chat with her in The Penny Hoarder Community.

This was originally published on The Penny Hoarder, which helps millions of readers worldwide earn and save money by sharing unique job opportunities, personal stories, freebies and more. The Inc. 5000 ranked The Penny Hoarder as the fastest-growing private media company in the U.S. in 2017.

How to Get 8 Free At-Home COVID Tests From Your Health Insurance

If you have private health insurance, you’re eligible for free at-home COVID tests starting Saturday, Jan. 15. The Biden Administration announced earlier this week that private insurers would be required to foot the bill for eight home COVID tests per month for each customer covered under a plan.

But finding tests could still be a challenge in the weeks to come. Also, many insurers won’t have the systems in place that would allow customers to access tests without paying out of pocket. That means it’s likely that you could have to pay up-front for tests and then submit a claim to reimbursement for your insurer.

Want to learn more about how to access free home COVID tests? Here’s everything you need to know.

Is My Insurance Company Required to Provide Free Home COVID Tests?

Yes, if you’re covered by a private insurance plan. If you have coverage through your employer or you bought a plan on the Affordable Care Act marketplace, your plan is required to cover the cost of eight tests per month.

Does Everyone in My Household Get 8 Free Tests?

Yes. The mandate requires insurers to cover eight free tests each month for each person covered under a plan. If you have a family of four and everyone is insured under your plan, your household can receive 32 tests per month.

How Do I Get My Free COVID Testing Kits?

Check with your insurer about whether it has a network of preferred pharmacies and retailers. If you get your test from within your insurance company’s network, you should be able to get your tests with no out-of-pocket cost.

You can also buy your test elsewhere and submit a claim for reimbursement. If you go that route, be sure to save a copy of your receipt. But be aware that your insurer can cap reimbursement at $12 per test if it has a preferred network and you choose to go out of network. If your insurance company doesn’t have a preferred network, they’re required to cover 100% of the cost no matter where you buy your testing kits.

Pro Tip

If your insurer requires you to submit a claim for reimbursement, purchase your COVID tests separately from other items and get a receipt to streamline things.

Will I Need to Pay Up Front?

Check with your insurance company. But there’s a good chance you’ll need to pay out of pocket for tests at the beginning. As The New York Times reported, home tests don’t have the billing codes that insurers need to process claims. Many insurance companies will require customers to save their receipt and submit a claim for reimbursement, just as you would if you went out of network for care.

Can I Buy All 8 Tests at Once?

Yes. You’re allowed to buy all eight tests at once or space out your purchases throughout the month. But keep in mind that as of this writing on Jan. 14, 2022, testing kits remain in extremely short supply.

What if I Don’t Have Health Insurance?

The federal government is purchasing 1 billion home tests and will soon launch a website that will allow anyone to request a free home test. You can also go to a community health center that offers free rapid tests.

Can I Get Free Tests if I’m on Medicaid?

Yes. State Medicare programs and Children’s Health Insurance Programs were already required to cover home testing kits under the American Rescue Plan, the $1.9 trillion COVID relief bill that passed in March 2021.

Can I Get Free Tests if I’m on Medicare?

At-home tests aren’t covered by original Medicare. If you have a Medicare Advantage plan, check with your plan about whether they’ll pay for home testing. You can also access free tests once the federal test-ordering website launches or go to a community health center for rapid testing.

Will the VA Cover Home Tests?

Veterans Affairs won’t send out free tests for now, but in many circumstances veterans can receive free testing at VA hospitals. Once the federal website launches, veterans will also be able to order free tests.

Will I Get Reimbursed for Tests I’ve Already Paid for?

Check with your insurer. Insurance companies aren’t required by federal law to retroactively cover home tests purchased before Jan. 15, 2022. However, some states already require insurers to cover at-home tests.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to AskPenny@thepennyhoarder.com or chat with her in The Penny Hoarder Community.

This was originally published on The Penny Hoarder, which helps millions of readers worldwide earn and save money by sharing unique job opportunities, personal stories, freebies and more. The Inc. 5000 ranked The Penny Hoarder as the fastest-growing private media company in the U.S. in 2017.

Dear Penny: Do I Tell My Mother-in-Law Her Retirement Plans Are Screwed?

Dear Penny,

My in-laws are hardworking folks who have never had much money, nor have they been good at managing it.

By his mid-20s, my partner was already in a caretaker role with them both with some light money management and my father-in-law's extensive health issues. This care is part of what made me fall in love with him. He's been able to hold firm boundaries through the years, allowing us to help when needed but still enjoy our warm relationship with them.

Several years ago, an elderly family member became ill. This family member was close to my in-laws a long time ago, but they'd lost touch as everyone aged. When this family member's power of attorney attempted to defraud her, my in-laws stepped in to manage her finances and her medical care since she has no other living family.

It quickly became clear this task went beyond my in-laws’ abilities. While they didn't want our help, my partner eventually had to intervene. This family member was about to be homeless, and my in-laws were essentially clueless. My partner was able to secure federal benefits for this family member that covered large portions of her care. This took a lot of the strain from my in-laws, and we thought all was well.

But we recently learned my in-laws took out a gigantic loan to cover some of this family member's nursing expenses before she died last year. Not only is the loan huge, but the interest rate is terrible. My father-in-law told my partner they inherited a few thousand dollars from her, but they decided to keep it rather than apply it to the loan.

My father-in-law's health continues to be poor, and my mother-in-law is beyond overwhelmed. My father-in-law has long been the manager of the family's finances, but he's terrible at it and my mother-in-law doesn't like to intervene. It's possible she's not aware of the details of the loan. She's close to retirement age, but this loan on top of their monthly expenses threatens her ability to retire completely.

With some assistance, I think they could manage the debt and even determine if any of this family member's federal benefits will cover a portion of it. But is there any way to present this information in a way that they'll accept? I'm tempted to use some direct language with them, like, “Without refinancing this loan you won't be able to retire.” But my partner worries that will just add to my mother-in-law's already paralyzing anxiety. 

What should they do first to manage this loan? Which financial services can we put them in touch with in the future so if they don't want to come to us, great, they can go to this person?

-Loan, Loan Go Away

Dear Loan Go Away,

Your in-laws are adults who are allowed to make bad choices if they want. But unsolicited advice rarely goes well. Even when the motives are good, the person on the receiving end usually feels like they’re under attack. And if your mother-in-law already has severe anxiety, starting the advice by telling her that she may never be able to retire will make matters worse.



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Your partner needs to take the lead here because these are his parents. He should try to make this a conversation instead of a lecture.

He should ask his parents if they’d be OK with sitting down to discuss a few financial matters. Tough conversations are best had when no one feels ambushed. Ideally, the three of them would have this discussion together.

Your partner should ask his parents some neutral questions. How big is the balance? How much is the interest rate? What are the monthly payments?

You say you’re not sure if your mother-in-law is aware of the details of the loan. But I wouldn’t assume your father-in-law is fully aware, either. Sometimes when people are overwhelmed by debt, they have no idea what they owe or what it’s costing them.

Once your partner gets the facts of the situation, then he can ask his parents how they’re feeling. Do they feel worried about whether they’ll be able to repay the loan? What about after his mother retires?

If your partner is worried that his parents can’t afford the loan, then he should say to them something to the effect of “I’m worried about whether you can afford these payments, but I think you have options. Could we discuss them?”

The point is to keep the message judgment-free. Telling your in-laws that they’ve made poor money management decisions will only put them on the defensive. But I’d urge your partner not to shy away from this discussion out of concern for his mother’s anxiety.

If your in-laws are willing to discuss their options, your partner could suggest they meet with a financial counselor. Unlike financial planners and financial advisers, who typically work with wealthier clients, financial counselors help lower- and middle-income clients with basic money management. They often work with clients struggling with debt.

You can search the Association for Financial Counseling & Planning Education’s website for a financial counselor in your state. Many charge on a sliding scale. If your in-laws are open to the idea, your partner could offer to pay the fees.

Bringing in a third party may be beneficial here. A professional isn’t going to have an emotional stake in this game. Plus, sometimes people are more willing to listen to guidance when it isn’t coming from family.

Ultimately, though, managing this loan is up to your in-laws, not you and your partner. Respect their boundaries, even if you don’t agree with their decisions.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to  or chat with her in The Penny Hoarder Community.

This was originally published on The Penny Hoarder, which helps millions of readers worldwide earn and save money by sharing unique job opportunities, personal stories, freebies and more. The Inc. 5000 ranked The Penny Hoarder as the fastest-growing private media company in the U.S. in 2017.

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