One thing nobody has mentioned yet - look into whether you qualify for the Child and Dependent Care Credit if you're taking classes. If you're going to school to be able to work, and your boyfriend is paying for childcare so you can attend classes, he might be eligible for this additional credit when he claims your son.

I was in a very similar situation last year! My partner and I aren't married, I stayed home with our 18-month-old while taking online courses, and he was the sole income earner. Here's what we learned after consulting with a tax professional: Your boyfriend should definitely claim your son as a dependent - this will unlock the Child Tax Credit ($2,000) and potentially the Earned Income Credit depending on his income level. Since you have no income, these credits would be wasted if you filed. For Head of Household status, your boyfriend needs to provide more than half the cost of maintaining the household AND have a qualifying person (your son) living with him for more than half the year. If both conditions are met, HOH gives him a much better standard deduction than filing single. Regarding claiming you as a dependent - this could work in your favor! If your boyfriend provides more than half your support and you made less than $4,400 (which you did with $0 income), he can claim you too. This increases his standard deduction even more. Don't forget about education credits! If he's paying for your school expenses and claims you as a dependent, he might qualify for the American Opportunity Credit or Lifetime Learning Credit, which could be worth up to $2,500. The key is to make sure only one person claims each dependent and that all the IRS tests are met. Document everything - who pays what bills, childcare costs, education expenses, etc. - in case you ever need to prove the dependency claims.

I'm currently dealing with a very similar situation - $48k in tax debt from before marriage, and my spouse earns significantly more than I do. Reading through all these responses has been incredibly helpful, especially seeing actual success stories. One thing I'm still confused about is the timeline. For those who got approved, how long did the entire OIC process take from submission to final approval? I know the IRS says it can take 6-24 months, but I'm wondering about real-world experiences. Also, during the review process, did anyone have to provide additional documentation beyond what was initially submitted? I want to make sure I include everything upfront to avoid delays. The proportional expense allocation approach that several people mentioned makes complete sense, and I'm planning to use that method. It's reassuring to hear from people who actually got through this process successfully rather than just reading conflicting information online.

This thread has been incredibly helpful - I'm dealing with almost the exact same situation with about $52k in pre-marital tax debt and a spouse who earns substantially more than me. One thing I haven't seen mentioned yet is whether anyone has experience with what happens if you're in a community property state. I live in California, and I'm wondering if that affects how the IRS views household income and assets for OIC purposes, especially for pre-marital debt. Also, for those who successfully got OICs approved using the proportional expense method - did you use any specific language or templates for the explanation letter? I want to make sure I'm articulating the situation clearly to avoid any misunderstandings. The success stories here are really encouraging. It sounds like the key is proper documentation and clearly explaining that the debt predates the marriage, along with showing your actual proportional contribution to household expenses rather than just splitting everything 50/50.

Update for anyone in the same boat: my refund JUST hit my account about 5 minutes ago! Chime Bank, DDD 2/27, rejected last Thursday when they tried early deposit. So it's definitely coming through today!!

Congrats Dylan! So glad you finally got your refund! This whole thread has been super helpful - I'm dealing with the same situation (Chime, 2/27 DDD, early deposit rejection last week) and was getting really anxious. Still waiting on mine but seeing all these success stories today is giving me hope that it's just a matter of time. The IRS really needs to get their act together with these banking partnerships though - this early deposit rejection thing seems to be happening way too often this year!

One thing nobody's mentioned yet is that you need to be super careful about how the mystery shopping company reports your income on tax forms. Some companies will send you a 1099-MISC or 1099-NEC that includes BOTH your actual income (fees for completing shops) AND your reimbursements all lumped together. This can really mess up your taxes because reimbursements under an accountable plan shouldn't be taxable income. If they report it all as income, you'll be paying taxes on money that was just passing through (reimbursements). If your 1099 includes reimbursements, you'll need to report the full 1099 amount on your Schedule C, but then deduct the reimbursed expenses to get to your actual taxable income.

Just to add one more wrinkle to this discussion - if you're doing mystery shopping involving alcoholic beverages, there are some additional considerations. The IRS sometimes scrutinizes alcohol expenses more closely, even when they're legitimate business expenses for mystery shoppers evaluating bar service. Make sure your assignment details explicitly state that ordering alcoholic beverages was required as part of your evaluation. This documentation is crucial for supporting the business purpose if you're ever questioned. Also, if your mystery shopping involves evaluating delivery services (like GrubHub/DoorDash mystery shops), make sure you're tracking delivery fees and tips separately from the actual meal cost.

Watch out for state taxes too! We sold property from my grandmother's trust in Minnesota and were shocked to find out that MN has different rules than the federal government for stepped-up basis in certain trust situations. Also, if the cottage has been rented out at all or used for any business purpose, that complicates things further. In our case, part of the property had been occasionally rented, which created a partially different tax treatment.

One additional consideration for your Michigan cottage situation - make sure you understand the property tax implications of the transfer. In Michigan, when property passes through a trust to beneficiaries, it may trigger an uncapping of the property's taxable value under Proposal A rules, which could significantly increase future property taxes if you decide to keep the property rather than sell. Also, given that this is lakefront property, there might be special environmental or zoning considerations that could affect the sale process and timeline. Some Michigan counties have additional regulations for waterfront properties that could impact your tax planning. I'd strongly recommend getting a current appraisal to establish the exact stepped-up basis value, especially since lakefront property values can be quite volatile. The closer your sale price is to the date-of-death value, the less capital gains tax you'll owe. If there's been significant appreciation since your mother's passing, you might want to consider the timing of the sale for tax purposes.