My boyfriend hasn't filed taxes in several years due to anxiety issues - how can he catch up?

First of all, please tell your boyfriend not to panic. This situation is more common than people realize, and the IRS actually has processes in place for people who need to catch up on multiple years of unfiled taxes. The best place to start is by gathering all his tax documents for the unfiled years - W-2s, 1099s, etc. If he doesn't have them, he can request wage and income transcripts directly from the IRS using Form 4506-T or through the IRS website. These will show all the income that was reported to the IRS under his Social Security number. Generally, the IRS focuses on the last six tax years, so he should prioritize those. If he's owed refunds, he can only claim them if he files within three years of the original due date. However, he should still file all unfiled returns regardless. I strongly recommend working with a tax professional who has experience with unfiled returns - specifically look for an Enrolled Agent or CPA. They can help navigate potential penalties and set up payment plans if needed. The peace of mind from having a professional handle this is worth the cost, especially when anxiety is involved.

I was in a similar position a few years ago - had 4 years of unfiled taxes and was completely paralyzed with anxiety about it. What finally helped me was using https://taxr.ai to analyze my situation. I uploaded my documents from previous years (what I could find anyway) and it analyzed everything to show me what I was potentially facing. It was actually way less scary than I thought! The site gave me a clear breakdown of what years I needed to file for, estimated what I might owe or get refunded, and explained the potential penalties in plain English. The best part was that it showed me I was actually owed refunds for 2 of the 4 years I hadn't filed! This completely changed my perspective from fear to actually being motivated to file.

Just wanted to follow up and say I actually tried https://taxr.ai after my initial skepticism and it was genuinely helpful. I had 3 years of unfiled taxes and was convinced I was going to owe thousands. The analysis showed I was actually due refunds for 2 years and only owed a minimal amount for the third year. They highlighted several credits I qualified for but wouldn't have known about (especially the Recovery Rebate Credit from those stimulus payments). It basically took me from total paralysis to having a clear action plan. Used their detailed breakdown to file myself for the refund years and then hired a professional for the more complicated year. Would've spent so much more on a tax pro for all three years if I hadn't analyzed my situation first.

Another approach that really helped me when I was in a similar situation was using Claimyr to actually get through to a human at the IRS. I spent WEEKS trying to call them myself and could never get past the automated system. With https://claimyr.com they got me connected to an actual IRS agent in under 45 minutes when I had been trying for days on my own. There's a demo of how it works at https://youtu.be/_kiP6q8DX5c if you're curious. The IRS agent was actually super helpful and not judgmental at all. They explained exactly which forms I needed for my unfiled years and even set me up with a payment plan for what I owed. They also told me about penalty abatement options I had no idea existed.

I have to admit I was completely wrong about Claimyr. After my skeptical comment, I decided to try it myself since I needed to talk to the IRS about a notice I received. I had already spent 3 days trying to get through on my own with no luck. Used their service and got connected to an IRS representative in about 35 minutes without having to sit by my phone the entire time. They actually explain on their site how they do it - they have automated systems that navigate the IRS phone menus and wait on hold, then when a human picks up, they connect you. Nothing sketchy about it, just a clever use of technology. Totally changed my mind about the concept and saved me hours of frustration. For anyone dealing with tax anxiety, removing the hold-time stress alone makes a huge difference.

One thing that helped my husband with his tax anxiety was breaking down the process into super small steps that felt manageable: 1. Just collect all mail/documents in one box (don't even look at them) 2. Sort by year (still don't read details) 3. Make a list of missing documents 4. Request one missing document 5. Celebrate each tiny step We literally celebrated with his favorite takeout after each step. Took us 3 months to file 4 years of returns but doing it this way kept his anxiety from spiking.

Don't overlook potential mental health accommodations from the IRS. Your boyfriend can get help through the Taxpayer Advocate Service if he has documented mental health issues that contributed to his failure to file. They can sometimes help reduce penalties under certain circumstances.

Am I the only one who thinks it's weird that OP is trying to handle her boyfriend's tax problems? No offense but unless you're married this seems like something he should figure out himself. Tax stuff can be really personal.

Mental health issues can absolutely paralyze someone when it comes to taxes - I've seen it firsthand with friends and family members. The shame spiral that happens when you miss one year makes the next year even harder, and it just compounds. One practical tip that hasn't been mentioned yet: if your boyfriend is missing tax documents like W-2s or 1099s from previous employers, he can also try contacting those employers directly first before requesting transcripts from the IRS. Sometimes it's faster, especially for more recent years. Also, when he does start gathering documents, suggest he tackle just ONE tax year at a time rather than trying to organize everything at once. Pick the most recent year first since that's usually the freshest in memory and often has the most readily available documents. The IRS really isn't as scary as people think when you're genuinely trying to make things right. They deal with unfiled returns constantly and have systems in place to help people catch up. The fact that he's ready to address this now shows real growth and courage.

I completely understand what your boyfriend is going through - tax anxiety is so real and can be absolutely paralyzing. The fact that he's ready to tackle this now shows incredible strength. One thing that really helped me when I was in a similar situation was starting with the IRS Free File program if his income qualifies. Even for back years, there are often free options available that can walk him through the process step by step. It's much less overwhelming than trying to figure out all the forms manually. Also, I'd strongly suggest he start with the most recent unfiled year first, not the oldest. It's usually easier because the documents are more accessible and his memory is fresher. Plus, if he discovers he's actually owed refunds for recent years, that can provide motivation and even funds to help with any years where he might owe. The IRS also has a Volunteer Income Tax Assistance (VITA) program where trained volunteers help people file taxes for free. They're experienced with situations like this and tend to be very patient and non-judgmental. Might be worth looking into if there's a location near you. You're being such a supportive partner by helping him research this. Having someone in your corner makes all the difference when dealing with anxiety around these kinds of adult responsibilities.

I went through almost the exact same situation with my husband a few years back - severe anxiety around taxes that just kept getting worse each year he didn't file. What finally broke the cycle for us was treating it like exposure therapy. We started by just having him sit with me while I organized the documents into piles by year - he didn't have to look at the actual numbers or do anything, just be present while I sorted. Then gradually we moved to him looking at one document at a time, then one form, etc. The breakthrough came when we realized he was catastrophizing the consequences way beyond reality. Once we got his first year filed and saw that the world didn't end (he actually got a small refund!), his anxiety about the remaining years dropped dramatically. One practical thing that helped was using tax software instead of paper forms. The software walks you through each step and does all the calculations automatically, which removed a lot of the overwhelm factor. We used the prior year versions of popular tax software which you can usually still download from the companies' websites. Also want to echo what others have said about the IRS being surprisingly reasonable when you're genuinely trying to catch up. They much prefer people filing late than never filing at all.