Married or Single for biggest tax break with children and new home purchase?

But doesn't the "marriage penalty" hit at higher income levels? I thought getting married sometimes causes couples to pay more in taxes, not less?

The "marriage penalty" typically affects couples where both spouses earn similarly high incomes, pushing their combined income into higher tax brackets. In your specific case, since you're not currently working and your partner is the sole earner, you'd likely benefit from what's sometimes called the "marriage bonus." With one income being split across the married filing jointly brackets, plus the higher standard deduction and potentially more favorable child tax credit situation, marriage would likely reduce your overall tax burden rather than increase it.

Does it actually explain WHY one status is better than the other? Or does it just give you numbers? I want to understand what's happening with my taxes, not just be told what to do.

How secure is this? I'm always nervous about uploading my tax documents to random websites. Do they store my information?

It actually breaks down exactly why one status is better, showing side-by-side comparisons of deductions, credits, and tax brackets that apply in each scenario. It's like having a tax professional explain everything to you in plain English. Their security is top-notch - they use bank-level encryption and don't store your documents after analysis. Once you get your results, your documents are purged from their system. I was skeptical too but their privacy policy is really clear about this.

Wait, so they just call the IRS for you? How is that even a service? Couldn't I just do that myself?

Sounds like a scam. No way they can get you through to the IRS faster than just calling yourself. The IRS phone system is notoriously backed up for everyone.

They don't just call for you - they use their technology to navigate the IRS phone system and secure your place in line. Have you tried calling the IRS lately? The average wait time is over 2 hours, and many calls get disconnected. Their system holds your place and only calls you once an actual human IRS agent is on the line. No, it's definitely not a scam. They don't handle any of your personal tax information - they just connect the call. The difference is their system can monitor multiple lines simultaneously and navigate the complicated IRS phone tree automatically. You're still talking directly to IRS agents, just without the hours of waiting and frustration.

Isn't there also something about head of household status? If they're not married, could the boyfriend file as head of household since he has dependents? How would that compare to married filing jointly?

Yes, head of household status is another consideration. If they're not married, the partner who has the children as dependents could potentially file as head of household, which has more favorable tax rates than filing as single. However, in most cases with one income and multiple children, married filing jointly still provides better overall tax benefits than one person filing head of household and the other filing single. The married filing jointly status usually provides lower overall tax rates, a higher standard deduction, and can make qualifying for certain credits easier.

Did you have to do anything special to prove you were married since it was so close to the end of the year? We're thinking about doing the same but worried about documentation.

No special documentation needed! As long as you have your marriage certificate, that's all the IRS requires. We got married on December 28th and just filed our taxes with the marriage certificate as proof. The IRS doesn't care what day in December you get married - you're considered married for the entire tax year. Just make sure to keep a copy of your marriage certificate with your tax documents for your records.