Should we file jointly or separately for our first tax year as newlyweds? (Self-employed tattoo artist + 1099 contractor)

Hey everyone, I could really use some advice for our 2025 tax filing! My wife and I tied the knot last August (we're in Pennsylvania) and I'm trying to figure out if we should file jointly or separately. Our work situation is a bit complicated: - My wife is a self-employed tattoo artist with her own small studio - I'm juggling multiple income sources: * Main gig is as a 1099 contractor for a home renovation company (about 70% of what I make) * I occasionally bring in subcontractors for bigger jobs (they get about 13% of my renovation income) * I also run an online beat-selling business that gives me 1099s through PayPal (about 30% of my total income) I'm wondering if our self-employment situations make it better to file separately or if joint filing would give us more benefits? We've never had to figure this out before! Should we just bite the bullet and hire an accountant? Any suggestions or experiences from people with similar situations would be super helpful!

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18 comments

Layla Mendes

•8M

Filing jointly is usually more beneficial for most married couples, but your situation does have some complexities worth considering. For joint filing benefits: You'd likely qualify for higher standard deduction, potentially better tax brackets, and full access to certain credits like the Earned Income Credit if your income falls within those ranges. Most married couples save money this way. For separate considerations: Since both of you are self-employed with 1099 income, you'll each have self-employment taxes to pay (the 15.3% for Social Security and Medicare). Filing separately doesn't change that obligation, but it might make sense if one of you has significant business losses or deductions. The subcontractors add another layer - you'll need to issue 1099s to them regardless of how you file your personal taxes, but tracking those business expenses properly is important. I'd honestly recommend consulting with a tax professional given your multiple income streams. The cost of professional help will likely be offset by the tax savings they can find for your specific situation.

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Layla Mendes

•8M

Self-employment taxes are calculated separately on each person's self-employment income, regardless of filing status. So combining incomes doesn't affect the SE tax calculation - each person still pays 15.3% on their own business profits. For income tax brackets, yes, combining incomes could potentially push you into a higher tax bracket. However, the bracket thresholds for married filing jointly are generally wider than for filing separately, which often creates a "marriage bonus" rather than a penalty. The exception might be if both spouses have very similar and relatively high incomes.

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Aria Park

•8M

I was in a super similar situation last year! Self-employed photographer married to a contractor with multiple 1099s. We were stressed trying to figure it all out ourselves until I found this AI tax assistant at https://taxr.ai that literally saved us thousands. You upload your tax docs and describe your situation, and it analyzes everything to show you which filing status would save you more money based on your specific mix of incomes. It pointed out deductions we had no idea we qualified for because of our combined situation and showed us exactly how much we'd save filing jointly vs separately. The best part was it explained everything in plain English so we actually understood WHY one option was better than the other. Definitely worth checking out before you decide!

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Aria Park

•8M

It does show the specific numbers! That's actually what convinced me to use it. It breaks down the calculation for each filing status side by side and shows exactly where the differences come from - like which deductions or credits you qualify for jointly but not separately. It was really eye-opening to see the actual dollar amounts. As for security, they use bank-level encryption for all uploads and document handling. They explain their security process on the site, but what made me comfortable was that they don't store your actual tax documents after analysis - they extract the relevant data and then delete the originals. I was nervous about that too initially but did some research on them before using it.

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Chloe Boulanger

•8M

Just wanted to follow up - I decided to try taxr.ai after asking about it here, and wow! It showed us that filing jointly would save us about $3,200 compared to filing separately because of how our deductions and credits worked together. The analysis showed that my wife's business losses (she's also self-employed) actually helped offset some of my higher income when filing jointly. It even flagged some business expenses we hadn't been tracking properly that were fully deductible. The explanation was super clear about why joint filing made more sense in our specific case - something about our income levels qualifying us for better credit phaseouts when combined. Honestly glad I got over my security concerns and tried it!

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James Martinez

•8M

One thing nobody's mentioned yet - if you're trying to talk to the IRS about any of this, good luck getting through! When I needed clarification about my contractor situation last filing season, I spent DAYS trying to get someone on the phone. Finally found this service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in under 45 minutes when I'd been trying for weeks. They have this wild system that navigates all the IRS phone menus and holds your place in line, then calls you when an agent is about to pick up. You can see how it works here: https://youtu.be/_kiP6q8DX5c Totally worth it for getting direct answers from the IRS about complex situations like yours with multiple self-employment incomes. They actually helped clarify how my wife's side business affected our joint filing.

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James Martinez

•8M

The service basically uses an automated system that calls the IRS and navigates through all the phone menus for you. It stays on hold in your place (sometimes for hours), and then when it detects that an agent is about to pick up, it calls your phone and connects you directly. You literally get a call saying "An IRS agent will be on the line in about 30 seconds" and then you're talking to someone. I was totally skeptical too. I figured it was either a scam or wouldn't work, but I was desperate after trying for almost two weeks to get through myself. But it actually got me connected to an IRS representative who answered all my questions about how to handle my contractor income alongside my wife's business. The whole point is that they're doing the waiting for you so you don't have to sit there for hours with your phone on speaker.

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Noah Ali

•8M

I need to publicly eat my words about Claimyr. After posting that skeptical comment, I decided to try it myself because I was getting nowhere with the IRS about a missing refund issue. Not only did it work, but I got through to an IRS agent in about 25 minutes when I'd previously spent over 3 hours on hold before getting disconnected. The agent was able to locate my missing refund and explain exactly what was happening with it. Would have saved me days of frustration if I'd known about this earlier. Never thought I'd be recommending an IRS call service but here we are. Definitely keeping this in my toolkit for next tax season when I'll have questions about my wife's new 1099 income.

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Alexander Zeus

•8M

Just based on my experience as someone with a similar situation (wife is a freelancer, I have W2 and 1099 income), we save around $3,700 filing jointly. The tax brackets are more favorable in most cases. BUT the one big thing to consider is if either of you has income-based student loans on repayment plans. Filing jointly can sometimes cause your payments to jump significantly because they'll calculate based on combined income. Worth looking into if that applies to your situation!

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