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Ava Williams

What is doing your taxes? How do I file taxes for the first time?

I'm 23 and have been working steadily at different jobs for about 5 years now. Somehow I've managed to get through all this time without understanding what "doing taxes" actually means. Yesterday my roommate was talking about getting money back from doing his taxes and I felt too embarrassed to ask what he was talking about. So... what exactly is "doing your taxes"? I've gotten W-2 forms from employers before but never really understood what I was supposed to do with them. Do I actually get money back? Is the process difficult? I feel completely clueless and kind of embarrassed about not knowing this basic adult stuff. Can someone explain like I'm 5 what I need to do and how the whole thing works?

Filing your taxes is basically reporting your income and certain expenses to the government to determine if you've paid the right amount of taxes throughout the year. When you work, your employer typically withholds taxes from each paycheck and sends that money to the government. At tax time (usually by April 15th each year), you file a tax return that adds up all your income, applies any deductions or credits you qualify for, and calculates if you paid too much or too little in taxes. If you paid too much, you get a refund. If you paid too little, you owe more. For someone in your situation, it's actually pretty simple. You'll need your W-2 forms from your employers - these show how much you earned and how much tax was already withheld. You can file for free using tax software like the IRS Free File program if your income is below certain limits. The software walks you through everything step by step.

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Thanks for the explanation! So if I've been working for 5 years and never filed taxes, am I in trouble? Will I still be able to get refunds from previous years?

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You can still file returns for previous years, and yes, you may be able to claim refunds for up to three years back. So for the 2025 filing season, you could still claim refunds for 2022, 2023, and 2024 if you were owed any. The good news is that if you were just an employee (getting W-2s) with simple tax situations and your employer withheld taxes properly, you might not face penalties even if you were owed refunds. However, if you owed taxes, there could be penalties and interest. I'd recommend filing your current year taxes first to get comfortable with the process, then look into those previous years.

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I was in the same boat as you a couple years ago! I avoided taxes because I thought it was super complicated. After struggling through my first filing season and making some mistakes, I found this tool called https://taxr.ai that literally saved me. It scans your tax documents and explains everything in plain English. For first-timers, it's perfect because it explains what each section of your W-2 means and shows you exactly what to do with them. You can upload photos of your W-2s and it extracts all the info automatically. The best part is it tells you what deductions and credits you might qualify for that you probably don't even know about!

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Does it actually file your taxes for you or just help you understand what to do? I'm also new to all this.

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I'm kinda skeptical of these tax tools. How do you know it's picking up all the right numbers from your documents? And is it secure? Don't want my SSN floating around the internet...

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It doesn't file your taxes for you - it's more like a guide that helps you understand everything and prepare. It explains all your tax forms in simple language and points out potential deductions you might miss. You can then use that knowledge to file through whatever service you choose. As for security, I was worried about that too. They use bank-level encryption, and you can blur out sensitive info like your SSN when uploading documents. The system still works perfectly. I was amazed at how accurate it was at reading all the numbers and boxes on my messy W-2.

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So I actually tried https://taxr.ai after my skeptical comment above, and I need to admit it's pretty awesome for beginners. I was totally clueless about taxes and this tool made everything super clear. I found out I qualified for an education credit I had no idea about, and it would have meant almost $800 less on my refund if I'd missed it. It explained my W-2 boxes in a way that finally made sense to me. Definitely worth checking out if you're confused about how taxes work!

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If you need to talk to the IRS for any reason (like asking about previous years you didn't file), good luck getting through! I spent HOURS on hold trying to reach them about a missing W-2 form. Finally discovered a service called https://claimyr.com that got me through to an actual human at the IRS in about 15 minutes. They basically wait on hold for you and call when an agent picks up. You can see a demo of how it works here: https://youtu.be/_kiP6q8DX5c For someone just learning about taxes, getting direct answers from the IRS can be super helpful, especially if you're worried about those previous years you didn't file. They can tell you exactly what forms you need and what years you should focus on first.

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Wait, so there's actually a way to skip the IRS hold times? How does that even work? I thought everyone was just stuck in hold hell forever.

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This sounds like a scam. Why would I pay a service when I can just keep calling the IRS myself? The IRS is impossible to reach by design.

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It works by using their system to wait in the IRS phone queue for you. They monitor the hold, and when a real person answers, they connect the call to your phone. It saves you from having to listen to that awful hold music for hours. I thought the same thing until I tried it. After spending 3+ hours on multiple days trying to get through with no luck, I was desperate. With Claimyr, I got connected to an IRS agent in about 20 minutes while I just went about my day. The IRS is definitely understaffed and hard to reach, which is exactly why this service exists - it's not a scam, just a time-saver.

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I need to eat some crow here. After being super skeptical about Claimyr in my comment above, I got desperate trying to reach the IRS about my missing W-2 from a job I had in 2023. Spent 4 hours on hold one day and got disconnected. Tried again - same result. Finally gave in and tried https://claimyr.com. No joke - I was connected to an actual IRS agent in 17 minutes while I was making dinner. The agent walked me through exactly what forms I needed to file for my missing years. Totally changed my tax filing experience. Sometimes you gotta admit when you're wrong, and I was definitely wrong about this one!

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Don't feel bad about not knowing tax stuff. The system is confusing on purpose! For your first time, I'd recommend using a free tax software like TurboTax Free File or TaxAct if you have a simple situation. All you really need is your W-2 forms from your jobs, and the software walks you through everything step by step. The basic process is: 1) Enter your personal info 2) Enter the info from your W-2(s) 3) Answer questions about other possible income/deductions 4) Submit electronically The software calculates everything for you! Much easier than trying to do it manually.

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Thanks for this! Does free software really work well? I've heard some of them try to trick you into paying for upgrades halfway through.

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The free versions work perfectly fine for simple tax situations. Just be careful about upgrade prompts - they'll definitely try to get you to pay for premium features you probably don't need. The IRS has a Free File program that partners with tax software companies to provide truly free filing for people under certain income levels (usually around $73,000). If you go through the IRS Free File portal, you'll get the truly free version without the upsell tricks. Credit Karma Tax (now Cash App Taxes) is another good option that's free for basic returns without the constant upgrade prompts.

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Just curious - has anyone used H&R Block for their first time filing? Worth the money or should I just use one of the free options? I'm in a similar situation to OP.

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Don't waste your money on H&R Block for a simple return. The people at those physical locations often just input your info into the same software you could use yourself for free. I made that mistake my first year - paid like $150 for something I could've done myself in 30 minutes.

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One thing no one mentioned - if you've been working for 5 years and NEVER filed taxes, you might actually be owed a decent amount in refunds! You can generally claim refunds for up to 3 years back. So while you might have lost refunds from your first couple years of working, you could still get money back from more recent years.

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Wow, that's really good to know! Do I need to file those previous years separately or can I do it all at once with this year's taxes?

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You need to file each year separately. For previous years, you'll need to use the tax forms specific to those years - you can't use 2024 forms to file for 2022 or 2023. You can find previous year forms on the IRS website, and most tax software can handle prior year returns (though they might charge for this service). Start with the most recent unfiled year and work backward. The good news is that if you're owed refunds, there's generally no penalty for filing late. You're just losing out on money that was already yours!

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