Congratulations on your upcoming wedding! As someone who works in tax preparation, I can confirm that everyone here has given you excellent advice. Your situation is actually pretty straightforward - at your combined income level of $161k, you'll almost certainly benefit from filing jointly rather than face any marriage penalty. One thing I'd add that might help ease your anxiety: the IRS has a "safe harbor" rule that can protect you from underpayment penalties in your first year of marriage. As long as you pay at least 100% of last year's tax liability (or 110% if your prior year AGI was over $150k), you won't face penalties even if you owe some additional tax when you file. Since you're both currently filing as single and presumably having appropriate amounts withheld, you're likely already close to meeting this safe harbor threshold. When you update your W-4s after the wedding (which you should definitely do), even a conservative adjustment should keep you well within safe territory. Also, don't forget that as newlyweds, you might be eligible for some additional tax benefits you couldn't claim when single - things like potentially higher limits on certain deductions or credits. Your first year filing jointly might be more beneficial than you expect! The most important thing is not to stress too much. Millions of couples go through this transition every year, and the tax system is designed to handle mid-year status changes. You're asking all the right questions, so you're already ahead of the game.

Isabella, congratulations on your upcoming wedding! I can totally understand the confusion - tax law can feel overwhelming when you're dealing with a major life change. But the good news is you're asking all the right questions and getting married mid-year is actually very manageable. Just to reinforce what others have said: yes, you'll be considered married for the entire 2025 tax year if you get married on August 15th. And at your combined income of $161k, you're in a sweet spot where filing jointly will almost certainly save you money compared to your current single filing status - no marriage penalty to worry about at your income level. Here's my practical advice: Don't try to solve everything before the wedding. Focus on enjoying your special day! After you get married, update your W-4s within the first month or two, and you'll have plenty of time to adjust your withholding for the remaining pay periods of the year. One tip that helped me when I got married - create a simple spreadsheet to track any tax-related changes you make throughout the year (W-4 updates, estimated payments, etc.). This will make tax season much smoother and help you understand how your decisions affected your final tax situation. You're going to do just fine! The fact that you're planning ahead shows you're already more prepared than most couples going through this transition.

Make sure you keep all documentation related to the settlement in case of an audit! I had a similar situation and the IRS questioned it three years later. Having the settlement agreement and evidence of the payment saved me from a huge headache. Also consider if any portion of the settlement was for attorney fees (even if you represented yourself) as there might be some deduction possibilities.

Just went through something similar last year. One thing to watch out for - if your settlement was over $600, the company is supposed to issue you either a 1099-MISC or include it on a corrected W-2, but many don't follow through properly. Don't wait for them to send the forms - you still need to report the income even without receiving the proper tax documents. I'd recommend reaching out to your former employer's payroll department to ask how they're reporting the settlement payment to the IRS. This will help you report it consistently. If they say they're not issuing any forms (which happened to me), document that conversation and report it as "Other Income" as others have mentioned. The key is being proactive since employers often drop the ball on settlement tax reporting.

I'm dealing with this exact same situation and it's been such a headache! My ex and I have had 50/50 custody for the past three years, and every tax season I get confused by these questions. What I've learned from my accountant is that even though you're not claiming your daughter as a dependent, you should absolutely still enter her information in TurboTax. When it asks about months, just be honest about your actual custody arrangement. Since she's with you part of every month, you could technically count all 12 months, but what really matters for tax purposes is the total number of nights. The key thing is to answer "Yes" when TurboTax asks if someone else can claim her as a dependent. This way the software knows not to give you the dependency exemption, but it will still check if you qualify for other benefits like Head of Household filing status or certain credits. I made the mistake my first year of not entering my son's info at all because I thought it would cause problems since his mom was claiming him. Turns out I missed out on some credits I was eligible for! Don't make the same mistake I did.

I've been helping parents with custody tax situations for years, and your confusion is totally understandable! Since you and your ex already agreed she's claiming your daughter this year, you actually don't need to worry about the months calculation for dependency purposes at all. However, you should still enter your daughter's information in TurboTax - just make sure to answer "Yes" when it asks if someone else can claim her as a dependent. This tells the software you're not claiming the dependency exemption, but it will still check what other benefits you might be eligible for. For the months question, with true 50/50 custody where your daughter is with you consistently throughout the year, you could technically count all 12 months since she's with you part of every month. But what really matters for other credits and filing status is the actual number of nights she stays with you. The important thing is being consistent and honest about your arrangement. Don't skip entering her info completely - you might miss out on credits you're eligible for even though you're not claiming her as a dependent. The tax code recognizes that parents can have different roles (custodial vs. claiming dependent) in shared custody situations.

Theres another angle to consider - if ur trading in both taxable and IRA accounts and do these transactions across accounts, the wash sale rules still apply but ur broker might not track them correctly. Made this mistake last yr and got hit with an unexpected tax bill 😩

Great question about cross-account wash sales! You're absolutely right that brokers often miss these. The IRS considers SPY and VOO to be substantially different securities even though they track similar indexes. SPY tracks the S&P 500 while VOO is Vanguard's S&P 500 ETF - they're different enough that selling SPY options at a loss and buying VOO shares wouldn't trigger the wash sale rule. However, if you sold SPY options and bought SPY shares (or other SPY options) across accounts, that would definitely be a wash sale that you'd need to track manually since your broker won't catch it.

Clay, I went through something very similar when I relocated my consulting business from Texas to Arizona in 2019. The IRS absolutely counts depreciation when determining profit/loss for the hobby rule, so that $14k in equipment depreciation will factor into your loss calculation. Since you're essentially in year 3 with losses, you need to be extra careful about documentation. The fact that you took a year off in 2023 might actually help your case - it shows you made a business decision to pause operations due to circumstances (partner's illness), rather than just continuing to rack up losses. For your restart in Colorado, I'd recommend: 1) Get a new EIN and business license to clearly document the "fresh start" 2) Create a detailed business plan showing path to profitability within 2 years 3) Keep meticulous records of all business activities and expenses 4) Consider quarterly estimated tax payments once profitable to show legitimate business intent The key is proving this isn't just a tax shelter hobby. Document everything - market research, business meetings, networking events, professional development. The IRS looks at the totality of circumstances, not just the profit timeline.

As someone who's dealt with similar Schedule C loss concerns, I want to emphasize that the IRS hobby loss rule is really about demonstrating genuine business intent rather than just hitting specific profit targets. The fact that you paused operations in 2023 due to your partner's illness actually works in your favor - it shows you made rational business decisions rather than blindly continuing to generate losses. A few key points for your Colorado restart: 1. **Documentation is everything** - Keep detailed records of your business activities, not just expenses. Time logs, client communications, market research, networking events all help prove business intent. 2. **The 5-year window is flexible** - Since you had legitimate business reasons for the pause, and you're essentially restarting with new equipment and location, you have a strong case that this demonstrates serious business commitment. 3. **Depreciation strategy matters** - While depreciation does count toward your loss calculation, bonus depreciation on legitimate business equipment actually supports your case for having a real business with substantial investment. 4. **Consider professional consultation** - Given that you're in year 3 with a restart, it might be worth having a tax professional review your specific situation to ensure you're positioning everything correctly for IRS scrutiny. The key is showing this is a legitimate business venture, not a tax-loss hobby. Your equipment investment and strategic restart suggest you're on the right track!