This is such a helpful thread! I've been dealing with a similar situation and had no idea about the pro-rata rule until reading through these comments. I've been making non-deductible contributions to my tIRA for the past 5 years while also having older deductible contributions, and I honestly thought I could just withdraw the non-deductible portions first without any tax consequences. The Form 8606 requirement is news to me too - I've definitely been filing my taxes wrong. It sounds like I need to go back and file amended returns for the years I made non-deductible contributions. One question I have: if I have multiple traditional IRAs at different brokerages, do they all get lumped together for the pro-rata calculation? Or is it calculated separately for each account?

Great discussion everyone! As someone who just went through a similar situation, I want to emphasize how important it is to keep meticulous records of all your IRA contributions, especially the non-deductible ones. I had a mix of deductible and non-deductible contributions spanning 15 years across three different brokerages. When I finally needed to start taking distributions, I realized I had never filed Form 8606 for about half of my non-deductible contribution years. The paperwork reconstruction was a nightmare! What saved me was creating a simple spreadsheet tracking every contribution by year, amount, and type (deductible vs non-deductible). I also scanned and saved all my 1099-R forms and brokerage statements. This made filing the missing 8606 forms much easier. For anyone in Brianna's situation - start organizing your records now before you need them. Future you will thank you when it's time to take distributions and you're not scrambling to prove which contributions were already taxed!

This is such a thoughtful question, and I love how you're approaching it practically while still honoring your relationship! One angle I haven't seen mentioned yet is the impact of potential changes to tax law. Tax policies can shift significantly over time, especially around marriage penalties/bonuses and child-related credits. For example, the Tax Cuts and Jobs Act made some changes to how marriage affects taxes, but many of those provisions are set to expire in 2025. If you're planning to have kids "within the next couple years," you might be making this decision based on current tax law that could change by the time those kids arrive. Also consider that your income trajectories might change once you start a family - if one of you plans to reduce work hours or take extended parental leave, that income difference could shift the marriage tax calculation significantly. What looks like a penalty now with similar incomes might become a bonus later with different earnings. Given all the great resources people have shared here (especially the tools for calculating different scenarios), you might want to model a few different future income scenarios alongside your current situation. The "right" financial answer might depend not just on where you are now, but where you expect to be in 3-5 years!

This is such a comprehensive discussion! As someone who works in tax preparation, I wanted to add a few practical considerations that might help with your decision-making process. First, don't forget about state-specific implications. Some states have community property laws that can affect how income and assets are treated even if you're not married, while others have significant state-level marriage penalties or bonuses that can dwarf the federal differences. Second, if you do decide to get married, consider the timing of major financial decisions in that first year. Things like retirement account contributions, FSA elections, and even job changes can have different tax implications when your filing status changes mid-stream. Finally, I'd suggest documenting your decision-making process and revisiting it annually. Tax law changes, income changes, and life circumstances evolve. What makes sense financially this year might not make sense in two years, and that's okay! Having a clear framework for re-evaluating helps take the emotion out of what can feel like a permanent decision. The fact that you're approaching this thoughtfully and considering both the emotional and financial aspects suggests you'll make the right choice for your specific situation. Good luck with whatever you decide!

Great thread everyone! I'm also dealing with this transition from college to first "real job" and the tax stuff is definitely confusing. One thing that helped me understand the new W4 was realizing that the old allowances system was basically just a rough way to estimate your tax situation, while the new form tries to be more precise about your actual circumstances. For what it's worth, I ended up in a similar situation as Samuel - filled out just the basic info initially, then monitored my first few paychecks. Turned out my withholding was pretty much spot on without any additional adjustments needed. The new system really does seem to work better for straightforward situations like ours. Also wanted to mention that if your employer has an HR department, they're usually pretty good at explaining how the new W4 works since they've had to help tons of employees through this same confusion. Mine even had a little cheat sheet that explained the differences between old and new forms, which was super helpful. Worth asking if yours has something similar!

As a tax professional who's helped dozens of clients transition to the new W4, I wanted to add some clarity to this discussion. The confusion about "claiming yourself" is completely understandable because the terminology changed so dramatically. Here's what's really happening: On the old W4, that "1" allowance you claimed for yourself was essentially telling your employer to reduce your tax withholding by a specific amount (roughly $4,300 worth of income in 2019). The new W4 eliminates this allowance system entirely and instead calculates withholding based on actual tax law. For recent graduates in your situation (single, one job, no dependents), the new system will typically withhold at the 12% federal tax bracket after accounting for the standard deduction. This often results in withholding that's very similar to what you would have gotten claiming "2" allowances on the old system. One important note: if you have student loan interest, you might want to complete Step 4(b) to reduce your withholding slightly, since that interest is tax-deductible. Most new graduates overlook this and end up with larger refunds than necessary. The bottom line is that the new system is actually more accurate for most people, even though the transition feels confusing!

I went through almost the exact same situation last year! Accidentally sent my entire tax payment (federal + state) to the IRS instead of splitting it. Here's what worked for me: 1. File Form 843 immediately - don't wait. The sooner you submit it, the sooner they can process your refund. 2. Include a detailed explanation letter with your form explaining exactly what happened, including the date of payment, amount, and payment method (pay1040.com in your case). 3. Keep copies of EVERYTHING - your payment confirmation from pay1040.com, bank statements showing the transaction, etc. 4. You can also try calling the IRS at 1-800-829-1040, but be prepared for long hold times. Sometimes they can process overpayment refunds over the phone if it's straightforward. The good news is that this is actually a pretty common mistake, so the IRS is used to handling these situations. I got my overpayment back in about 6 weeks. And definitely pay your state taxes ASAP even if you have to put it on a credit card temporarily - the interest on a card will be way less than state penalties and interest.

I've been through this exact situation! The most important thing is to act quickly on both fronts - getting your IRS refund AND paying your state taxes to avoid penalties. For the IRS overpayment, Form 843 is definitely the right form (not 8849 as someone mentioned earlier). Make sure to include: - Exact payment date and amount - Clear explanation that you accidentally paid state taxes to the IRS - Payment confirmation from pay1040.com - Your contact information Pro tip: You can actually request expedited processing if you're experiencing financial hardship due to the overpayment. Include a brief hardship letter explaining your situation. While you're waiting for the refund (typically 4-8 weeks), definitely pay your state taxes immediately even if you have to borrow the money temporarily. State penalties and interest rates are usually much higher than what you'd pay on a short-term loan or credit card. You can also try calling the IRS Taxpayer Advocate Service at 1-877-777-4778 if you're experiencing significant financial hardship. They sometimes can expedite overpayment refunds in genuine hardship cases. Good luck - this mistake happens more often than you'd think, so the IRS is used to processing these requests!

Just wondering - does anyone know if using TurboTax or another DIY software is reasonable for filing trust returns? My family is in a similar situation and we're trying to save on preparation fees.

I've been dealing with trust taxation for several years now, and I'd strongly recommend getting clarity on whether this is actually a grantor trust or a non-grantor trust before making any filing decisions. The fact that it was created when your dad's mom passed away suggests it might be an inherited irrevocable trust, which would typically be a non-grantor trust requiring its own Form 1041 filing. If it IS a grantor trust, then yes, everything flows to your dad's personal return regardless of whether you file a separate informational return. But if it's a non-grantor trust (more likely given the circumstances), then it must file separately and the trust itself pays taxes on retained income. The potential tax savings your dad's preparer mentioned could make more sense in a non-grantor trust scenario, where the trust can deduct administrative expenses against its own income. I'd suggest having the attorney review the trust document to confirm the grantor status before proceeding with any filing strategy.