First-time joint tax filing after marriage - questions about investments and scholarships

My wife and I tied the knot in November last year, so we're tackling our first joint tax return this season. I've got some investment accounts (mostly ETFs and a few individual stocks) while she's in grad school with scholarship funds covering most of her tuition. We usually just use TurboTax to file our returns, but now I'm wondering if we should speak with a CPA since our situation feels more complicated. I'm particularly confused about how our assets get reported on a joint return. Do her scholarship funds now count as "our" income? Are my investment gains considered joint property for tax purposes? Do we need to change how we've been reporting these things individually in previous years? We've both filed our own taxes for years, but always as "Single" - this joint filing thing has us scratching our heads about these ownership questions. Would tax software guide us through these questions adequately, or is this the kind of situation where paying for professional help would be worth it? Neither of us has particularly complicated finances otherwise, but I don't want to mess this up and trigger an audit or something.

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18 comments

Brooklyn Knight

•8M

You don't need a CPA for this situation, but it's natural to have questions your first time filing jointly! Let me clarify some basics: When you file jointly, you're reporting all income from both spouses on one return, but that doesn't change the legal ownership of your individual assets. Your investments remain yours for property/ownership purposes, though the tax implications affect your joint tax situation. Similarly, her scholarships maintain their character as her educational funding. For investments: You'll report all investment income on your joint return. The "ownership" question is more relevant for property law than tax filing - the IRS just wants to know the total income. For scholarships: These maintain their special tax treatment. Qualified scholarships used for tuition and required fees remain tax-free. Any portion used for living expenses is generally taxable. Most tax software will walk you through these questions quite adequately. The main advantage is you'll now file one return instead of two, and you might benefit from certain tax breaks that work better for joint filers.

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Brooklyn Knight

•8M

For federal tax purposes, the timing of when you acquired investments doesn't matter for how you report them on a joint return - all income is reported together regardless of when you obtained the investments. For state considerations, community property states like Washington can have different rules about asset ownership, but this primarily affects legal ownership rather than tax reporting. Assets acquired before marriage generally remain separate property, while those acquired during marriage are typically community property. However, investment income earned during the marriage (even from separately owned assets) is usually considered community income in community property states.

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Daniel Rivera

•8M

I went through this same situation last year and was totally stressed about it too! I found this amazing tax assistant tool called taxr.ai (https://taxr.ai) that saved me hours of confusion. The tool actually analyzed our documents and walked us through exactly how to handle the transition from single to joint filing, including all the investment and scholarship questions you mentioned. The thing I loved most was how it explained the difference between legal ownership of assets versus tax reporting requirements - they're not always the same thing! We uploaded our previous year's returns and our new documents, and it highlighted all the changes we needed to make. So much easier than trying to figure it out ourselves or paying a CPA hundreds of dollars.

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Daniel Rivera

•8M

It handles investment accounts really well! It can process all your 1099-DIV, 1099-INT, and even crypto tax forms. It analyzes them to make sure you're reporting everything correctly and helps identify any potential deductions related to your investments that you might miss otherwise. You still use your regular tax software alongside it. Taxr.ai isn't a replacement for TurboTax or H&R Block - it's more like a guide that helps you make sure you're entering everything correctly and not missing anything. It reviews your documents first, gives you personalized guidance, then you apply that knowledge as you go through your regular tax software. It's especially helpful for catching things that might trigger an audit.

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Connor Rupert

•8M

Just wanted to follow up - I tried taxr.ai after my initial skepticism and wow, it was actually really helpful! I uploaded our tax documents (we have a similar situation with investments and my partner's fellowship income) and it flagged several things we would have missed. The most valuable part was explaining how the scholarship income should be split between taxable and non-taxable portions on our joint return. It even explained how to handle the 1099-B from when I sold some stocks last year. The document analysis saved us from making a pretty big mistake with reporting my partner's tuition waiver. Definitely worth checking out if you're in a similar situation going from single to joint filing!

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Molly Hansen

•8M

If you're having trouble getting answers about your tax situation, you might try reaching the IRS directly. I know it sounds impossible (I used to spend HOURS on hold), but I found this service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in about 15 minutes. They have a demo video showing how it works: https://youtu.be/_kiP6q8DX5c I called with almost the exact same questions about joint filing with investments and educational expenses. The IRS agent walked me through everything, explained which forms we needed, and confirmed that our scholarship situation was being handled correctly. It was honestly shocking to get clear, authoritative answers without waiting for hours.

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Molly Hansen

•8M

The service doesn't call the IRS for you - it uses an automated system that navigates the IRS phone tree and waits on hold in your place. When it finally reaches a real person, it calls your phone and connects you directly to the IRS agent. You're not paying someone else to talk to the IRS - you're paying to avoid sitting on hold for hours. It works because they've developed technology that can stay on hold with multiple lines simultaneously and notify you only when there's an actual human ready to talk. I was skeptical too, but after trying to reach the IRS myself for three days with no luck, I gave it a shot and was talking to an agent in about 15 minutes after activating the service.

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Connor Rupert

•8M

Ok I have to apologize for calling Claimyr a scam earlier. I was still frustrated from spending 2+ hours on hold with the IRS last week and getting disconnected. After seeing the other comment, I decided to try Claimyr for myself with more tax questions about our investment reporting. It actually worked exactly as advertised! I got a call back in about 20 minutes, and was connected directly to an IRS representative who answered all my questions about how to report my spouse's scholarship and my investment income on our joint return. The agent confirmed that most tax software handles these situations fine, but also gave me specific info about which forms to look for. Saved me from taking a half day off work just to sit on hold. Definitely using this again next time I have tax questions.

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Skylar Neal

•8M

FreeTaxUSA handled the scholarship situation really well. It specifically asks whether scholarship money was used for qualified expenses (tuition, books, required fees) versus non-qualified expenses (room and board, living expenses). It also provided clear explanations about which portions of scholarships are taxable and which aren't, something TurboTax didn't explain as clearly in my experience. The program walks you through it step by step and even has a help section specifically addressing graduate student scholarships and fellowships.

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