12 With your income difference ($95,000 vs. $42,000), you'd likely receive a "marriage bonus" by filing jointly. The marriage penalty typically affects couples when both spouses earn high, similar incomes that push them into higher tax brackets when combined. In your case, your higher income would be partially taxed at your fiancée's lower rates when combined, resulting in tax savings. Based on 2025 projected tax brackets, you could save approximately $2,100-$2,800 by filing jointly compared to both filing as single. The exact amount depends on your deductions, credits, and other tax situations, but with that income spread, you're definitely in the "bonus" category rather than the "penalty" zone.

10 When you updated your W-4s, did you have to do anything special? Or just check the "married" box? I'm getting married in June and don't want to mess this up.

9 Just checking the "married" box isn't enough! The W-4 form changed a few years ago, and you actually need to coordinate between both spouses now. If both of you work, there's a specific section for "multiple jobs" that you need to complete. The easiest way is to use the IRS withholding calculator online. My husband and I both had to adjust our withholding amounts to account for our combined income pushing us into a higher bracket. One of us actually had to withhold at the "single" rate even though we're married to avoid owing at tax time. It's confusing but worth getting right!

If I get rid of these partnership investments now, will I stop getting K-1s next year? This is all way more complicated than I signed up for when I started investing.

Yes, if you sell all your partnership investments now, you won't receive K-1s for those investments next year. You'll just have a final K-1 for this tax year that includes the sale. Just be careful about which investments you're selling. Look specifically for anything labeled as MLP (Master Limited Partnership), LP (Limited Partnership), or PTP (Publicly Traded Partnership) in your portfolio. Don't just randomly sell investments because most normal stocks and many ETFs don't generate K-1s. Some platforms like Robinhood actually mark which investments might generate K-1s in their descriptions.

Bad idea. The IRS gets a copy of your K-1, so they know you received partnership income even if you ignore it. Ignoring it basically guarantees an audit or at minimum a tax notice and potential penalties. A friend tried this and ended up owing the original tax plus a 20% accuracy penalty and interest.

That makes sense from a business strategy perspective. Do most POS systems automatically track this for you? I'm using a pretty basic one right now and doing some calculations manually which is where I noticed this issue.

Most modern POS systems have tip tracking features, but they vary in sophistication. Basic systems might just record the tips but not calculate the tax implications. More advanced restaurant-specific POS systems will actually estimate your employer FICA obligation from tips and can generate reports for payroll. If you're using a basic system, it might be worth upgrading if tips are a significant part of your business. In the meantime, a simple spreadsheet that calculates 7.65% of reported tips will give you a quick estimate of your additional tax responsibility. Some owners I know actually set aside this percentage from daily sales automatically to cover the eventual obligation.

Each employer is separately responsible for their own FICA taxes on tips earned at their establishment. Your employee needs to keep tips separate by workplace and report them accordingly to each employer. You're only responsible for tips earned while working for you.

Do those services automatically generate and file the 1099-NECs at the end of the year? That's my biggest headache with contractors.

Yes, all three services I mentioned can automatically generate and e-file 1099-NECs based on the payments you've processed through them throughout the year. They collect and verify contractor W-9 information upfront and track all payments. QuickBooks is probably the most comprehensive if you use their accounting system too, but even standalone Melio or Bill.com will handle the 1099 filing process. They usually charge a small fee per 1099 (like $3-5 each), but the time saved and accuracy is absolutely worth it compared to manually preparing them.

I agree with this. I've been running a small photography business for 5 years and have occasionally messed up payment classifications. As long as you issue the correct 1099s at tax time, how you actually transferred the money is less important. The IRS wants the income reported correctly on both sides.

Whoa I had no idea there were different penalties! So if I file on time but can't pay everything, I'll only get the smaller penalty? Is there any way to avoid penalties completely if I just need like an extra month to pay?

Exactly! Always file on time even if you can't pay - the filing penalty is 10 times higher than the payment penalty. It's one of the most expensive mistakes new filers make. If you just need an extra month or two, you might qualify for a short-term payment plan with minimal or no setup fee through the IRS website. For extremely short delays (like a few weeks), sometimes you can call and request a one-time extension without penalties, but this is case-by-case and not guaranteed. Your best bet is to pay as much as you can by April 15th to minimize the amount subject to penalties, then set up a formal payment arrangement for the rest.

Most states align their deadlines with the federal April 15 date, but not all do! For example, Virginia's deadline is May 1st, and Hawaii's is April 20th. Always check your specific state's tax website to confirm.